Kentucky Derby Hats: The History Behind the Fashion

A few years ago my friends and I went on a girls’ trip to the Kentucky Derby. During the race, there was a crazy woman standing in the infield screaming “You’re all winners!!!” at the horses as they sped around the track. That crazy woman was me.

Truth be told, I don’t care for horse racing or any sport that exploits animals for entertainment. And while I’m not a fan of the Kentucky Derby itself (too many horses dying) – I do love the fashion. In fact, I think they should do away with the horse race altogether and just make it one big drunken fashion show where everyone struts around the track in their best hats!

It rained when we attended the Derby in 2019, so our hats were not just fashion statements. They protected us from a very bad hair day. As you can tell from the photos below, the rain certainly didn’t stop us from having a blast. Or maybe we’d just had one too many mint juleps.

As a vintage collector, curator, and seller, I wanted to understand the history of the Derby hat and how it became such an iconic fashion statement. So I went straight to the Kentucky Derby’s official site, which provided most of the details and photos for my research.

Here’s what I found.

Kentucky Derby hat styles through the decades

The 1870s

The first Kentucky Derby took place in 1875. This was the beginning of the “gilded age” in fashion.

The wide-brimmed and elaborately styled hats worn at the inaugural race would have been constructed of straw with satin and velvet trim and decorated with feathers.

The 1900s

In the decades that followed the first run for the roses, fashion became more streamlined and simple.

Kentucky Derby hats for women retained their wide brims and satin ribbons, but the extravagant plumes and feathers were absent.

The 1920s

The roaring 20s introduced “flapper” style and the popular bell-shaped cloche hat. (Cloche being the French word for “bell.”)

With its simple design and low brim, the cloche was definitely the most understated style of hats in Kentucky Derby fashion history.

The 1930s

Hats remained small in the 1930s, but the brim was lifted and many were worn tilted at an angle, paving the way for the popular pillbox styles.

Plumes and feathers returned as did wide satin and velvet ribbon trims.

The 1940s

In the 1940s, turbans and snoods became popular as the original “bad hair day” coverup during wartime, when women were working in the factories and money for regular hair appointments was tight.

Certain materials like felt and straw were scarce, so trimmings such as flowers, ribbons, feathers, and netting were used in greater quantities to construct larger-looking hats that influenced Kentucky Derby style in the late 40s.

The 1950s

Post World War II, the fashion industry longed for a return to glamour.

When Christian Dior launched his “New Look” collection in the late 40s, saucer and cartwheel hats became as popular as the new look itself, as they were quite complementary to the wider style skirts and dresses.

The 1960s

Wider brimmed hats became popular again in the 60s thanks to the floppy styles worn by the hippies and beatnik generation.

Whether adorned with a bouquet of flowers or a single satin bow, these Derby hats were a throwback to the original 1800s versions.

The 1970s

Both the hems on the pants and the brims on the hats got wider in the 70s.

Floppy hats continued to be popular throughout the decade, appearing at the Derby with wide brims and wide trims in satin and silk fabrics.

The 1980s

The only thing that got smaller in the 1980s when it comes to fashion were the hats.

While big shoulder pads and big hair were the trends of the decade, it was just the bright neon colors of the 80s that made it into the overall hat designs.

The 1990s

When I think of hat styles in the 1990s, I think of Julia Roberts in Pretty Woman and I also think of Princess Diana.

The hats of the 90s were definitely a flashback to the wider brims and more elegant styles of the 1950s and 60s.

The 2000s

Reality stars descended on the Derby during the 2000s, bringing much more attention to the fashion and the race itself.

While the clothing got smaller and the waistlines dropped lower, the hats definitely got bigger and brighter.

The 2010s

Okay, so my best friend Missy and I got in at the very end of the decade here in 2019.

The royal wedding of Prince William and Kate Middleton in 2011 made the fascinator hat fascinating again. I actually ordered this hat from Amazon and Missy wore this beautiful cream and black hat from my vintage shop.

So while Derby hats have changed throughout the decades, there are two things about Derby style that remain the same: creativity and individuality. My advice for dressing for any outdoor formal event is to start with the hat and build your entire look around it. Start at the top and the rest of the look will follow.

And let’s hope they either find a way to make horse-racing 100% safe and beneficial for the horses, or do away with it altogether. Fashion is fun. Animal abuse is abhorrent.

Check out some of the vintage hats available at Shop Stylaphile

The Top 5 Spring 23 Fashion Trends

What’s old is definitely new again.

Current fashion trends are always a throwback to previous decades. For Spring 2023, the trending styles are all about the 50s (polka dots), the 60s (mod florals and bright yellow), and the 70s (sequins and pleats).

So if you’re planning your spring outfits or buying spring clothing, here are some of the trends that were all over the runways this season, along with a flashback to their vintage counterparts.

Spring Fashion Trend #1: Polka Dots

Left: Chanel Spring 2023 (Vogue Runway) | Right: Vintage (Unbranded)



Spring Fashion Trend #2: Sequins

Left: Simkhai Spring 2023 (Vogue Runway) | Right: Vintage 90s Sequin Skater Dress



Spring Fashion Trend #3: Pleats

Left: Altuzarra Spring 2023 (Vogue Runway) | Right: Vintage Pleated Skirt (Unbranded)



Spring Fashion Trend #4: Yellow

Left: Monique Lhullier Spring 2023 | Right: Vintage 1970s Maxi Dress (Unbranded)



Spring Fashion Trend #5: Florals

Left: Lela Rose Spring 2023 (Neiman Marcus) | Right: Vintage 1960s Adele Simpson Maxi Dress



Like this post? Share it or leave a like or comment below! You can also check out these previous vintage fashion stories…

13 Going on 30 Outfits

Thirty, flirty and thriving.

While I’ll never be 30 again (nor do I want to), I certainly felt flirty and thriving while putting together these looks from one of my favorite movies. Jennifer Garner is an absolutely joy in this film. The entire cast is actually. Judy Greer’s “Tom Tom” to Garner’s Jenna Rink is a frenemies match made in movie heaven. (The fact that they’re best friends IRL makes it even better.) Even the soundtrack to this movie rocks. I mean, The Go-Gos, Rick Springfield, Pat Benatar, Billy Joel? Come on!

But the real star of this movie to me is the fashion. Costume Designer Susie DeSanto (who also did the costumes for Hope Floats and Miss Congeniality) succeeds in making us all nostalgic for the early aughts. Slip dresses, Fendi baguettes, pastel cardigans, and butterfly motifs were all the rage. I wore them all when I first moved to New York City in 2000.

And while the Jenna-Rink-Versace-dress-look has become a popular Halloween costume, many of the other outfits are just as fashionable today as they were back then. Here’s a look back at some of the best outfits from 13 Going on 30. (And if you haven’t seen it, or haven’t seen it in a while, do yourself a favor and watch it. Again. You can watch the full movie online here.)

The Slip Dress

Vintage Nanette Lepore Coat (slip brand unknown)


The Closet Scene


THAT Dress

Versace dress & Tarina Tarantino butterfly necklace (The necklace I’m wearing is Betsey Johnson)


The Polka Dot Dress (that’s only seen for a split second)

Moschino or Marc Jacobs dress (I think!) & the bag is either Prada or Fendi (couldn’t find an exact match)


The Lace-Up Blouse

Moschino blouse and vintage yellow skirt (she later wears this skirt with a Ralph Lauren strapless corset top)


The Black Leather Jacket

I think the dress is Roberto Cavalli but not sure about the jacket


The Chop Sticks

Christian Dior Corset Bag (not sure who made the jacket & pants)


The Chloe Ribbon Blouse

Chloe blouse & skirt


The All Pink Ensemble

Marc Jacobs skirt


The Moschino Dress That No One Can Find

Moschino dress


If you liked this post, check out the “Get The Look” posts I did for The Devil Wears Prada and Factory Girl – two of my other favorite fashion films.

Vintage 80s Clothing: 5 Things I Kept From High School

Some things you never throw away.

Everyone has that box up in the attic or down in the basement that holds pieces of our past… old memories we may want to revisit some day.

Being a collector who regularly scours consignment and thrift stores for other people’s vintage pieces, I recently climbed up into the attic and brought down my own box of history. It was filled with middle and high school annuals, printed photos (from a time when you actually had to get them developed) and lots of clothes.

Here are 5 vintage 80s clothing items that I kept from my high school years.

1. Letterman Sweater

Above right: A photo from my high school annual. That’s me in the middle (with blonde hair) wearing my letterman’s sweater in the homecoming parade. Below right: My dad’s football patch from Etowah High School, my mom’s majorette patch from Emma Sansom, and mine.

I remember the day my mom took me to the sporting goods store in the Gadsden Mall to order my letterman sweater. She was so proud of me.

It was my sophomore year of high school and my first year as a majorette. Mom was a majorette at the same high school in the 1950s, and she told me about how excited she was when she got her lettermans sweater.

When my mom passed away, I got several boxes of her things. In one of those boxes was her letterman sweater patch. Right next to it was one of my Dad’s football letterman jacket patches. I love the fact that she kept them, and the fact that I still have them now means more to me than she’ll ever know.

2. Pep-Rally Uniform

Above left: A photo of a few of the majorettes in our pep rally uniforms. I’m on the right in the back row (right under the “wine” sign, of course.)

Our pep-rally uniforms had our names embroidered across the front. One day, two of my majorette friends and I skipped the last two periods of school to drive across town to another school to see boys we were dating.

We thought we were so cool, showing up to a rival school in our little pep-rally uniforms. Unfortunately, the principal of that school did not think we were cool. He called our school and reported all three of us since our names were right there on our chests.

We got suspended for three days.

3. Varsity Sweatshirt

My high school had a bit of an identity crisis when it came to school colors. The marching band uniforms were red, white, and blue, but our school colors were actually purple and gold.

The majorettes wore these purple tracksuits when traveling to band competitions or during Christmas parades if it was really cold.

I only have the sweatshirt now. No clue what happened to the pants. I’ve been trying to order sweatpants to match, but I’ve yet to find the exact color.

4. 80s Sequin Sweater

Sequins were a big 1980s fashion trend. So was my big blonde hair. In the photo above, it looks like I’m emerging from a gas station loaded with Mountain Dew and Pepsi. I’m guessing my friend and I were en route to drive around the mall, which is what everybody did on Friday and Saturday nights in Gadsden, Alabama in the 80s.

I’m still a sucker for sequins, so I still wear this 80s style sweater.

5. Majorette Uniform

My red sequin majorette uniform is missing its stars. I wore it in college in a play called The Miss Firecracker Contest and the costume designer replaced the original stars with big silver ones that eventually fell off.

I had another majorette uniform my junior year that was silver instead of red, but I think my niece took it when she was younger. She also took my original Starline batons. (I recently ordered a new baton from Amazon because I missed twirling. Now I do it around the house just for fun. I even remember some of my old routines.)

I actually kept two of my majorette uniforms. This one is from middle school. Eighth grade to be exact. Check out my Princess Diana haircut.

I kept this uniform because it reminded me so much of the one my mom wore in the 1950s.

I only have the top now. I have no idea what happened to the shorts. I’m certain they wouldn’t fit me now anyway. The only reason I was able to zip up the top in the photo below is because I wasn’t wearing a bra!

But of course, the best thing I kept from high school is…

My friends.

I don’t get to see my high school friends as much as I’d like, but when we do get together, it’s like nothing has changed. We’re still the same group of girls we were back in the 80s.

Vintage friendship is by far the most valuable type of vintage you can ever own.

Sansom majorettes decades later. Me, my friend Kristi, my best friend Missy, and my friend Leslie in a hometown bar a few years back.

Shop 80s vintage clothing at Shop Stylaphile Vintage

The Little Black Dress: By the Decade

The first little black dress

There’s nothing little about it, really. It’s as iconic and larger-than-life as the person who invented it. Coco Chanel.

According to The Costume Institute, Chanel debuted the little black dress in 1926. Vogue quickly nicknamed it the “Ford of Fashion,” comparing the garment to the Model T car, which was very popular at the time. The drawing pictured on the left of Chanel’s original design appeared in the magazine that same year.

The first little black dress was long-sleeved, fell just below the knees, and was constructed of a wool jersey fabric. Chanel designed it to be a simple and unadorned foundation piece that could be worn with different accessories and dressed up or down according to the occasion.

Prior to World War I, women didn’t really wear black that often because the color was associated with mourning. In the period that followed (and especially during the Great Depression of the 1930s) black captured the collective mood of despair and became more acceptable. The little black dress required minimal fabric, so it was more affordable to produce at the time, making it even more popular.

In the decades that followed, the little black dress only increased in popularity, appearing on fashion runways and magazine covers in various forms: the pinup, the wiggle, the mini, the maxi, and more. Here’s a little sampling.

1940s Dresses: The Pinup

After years of fabric-rationing and factory uniforms, there was a strong desire for a return to more glamorous dressing. Enter Christian Dior.

In the 1940s, Dior came up with the famous “New Look” silhouette, featuring rounded shoulders, nipped waistlines, and full skirts. This design led to the “pinup” and “rockabilly” styles of the late 40s and mid-50s. Black was a dominant color.

“You can wear black at any age,” Dior stated at the time. “You can wear it on almost any occasion. A little black frock is essential to a woman.”

Shop the 1940s look

1950s Dresses: The Wiggle

The 1950s introduced another new look. The “wiggle” or “pencil” dress became popular when worn by movie stars including Marilyn Monroe and Audrey Hepburn.

The wiggle got its name in reference to the way a woman had to walk when wearing the dress. The straight hemline was more narrow than the hips, requiring her to take shorter strides and keep the legs close together when walking. This caused a swaying of the hips that became known as the “wiggle.”

The little black wiggle dress was certainly not the easiest to walk (or sit) in, but it was glamorous nonetheless.

Shop wiggle dresses

1960s Dresses: The Mini

The 1960s ushered in the rise of the hemline. The sexual revolution happening at the time freed women from strict dress codes and encouraged more expression in both sexuality and fashion.

Little black dresses got even littler thanks to designers like Mary Quant (who is credited with inventing the miniskirt) and André Courrèges (known for his space-age minidresses). Both designers were showing skirts and dresses that hit several inches above the knee.

Dresses in the 1960s were worn with go-go boots, platform shoes, or chic flats. Think Edie Sedgwick hanging out with Andy Warhol at The Factory.

Shop 1960s looks

1970s Dresses: The Midi and Maxi

The sexual revolution continued into the 1970s, but the hemlines retreated. The little black midi-dress replaced the mini-dress thanks to Studio 54 and the decade of disco. Prom and evening dresses went full-length maxi and were made of silk, satin, or polyester material.

Little black dresses from designers such as Halston, Bill Blass, Norma Kamali, Donald Brooks and Stephen Burrows were all popular during the 1970s.

It was also the decade that Diane von Furstenburg introduced the iconic wrap dress.

Shop 1970s Style Dresses

1980s Dresses: The Pouf

Pouf! There it is!

If you went to high school during the mid to late 1980s, you had a pouffy prom dress.

Whether the poof was at the shoulder or the hem, bigger was always better. (It wasn’t called the “Big 80s” for nothing. Something had to balance out all that hair!)

Aside from prom dresses, most dresses in the 80s had oversized shoulder pads and tons of embellishments, including sequins, beading, and chain detail, like this little black Lillie Rubin dress I’m wearing in the photo.

Shop 1980s dresses

1990s Dresses: The Bodycon

The 90s were a backlash to the over-the-top opulence of the 80s. Dresses became more streamlined. Emerging grunge and goth trends throughout the decade made black the go-to color.

Slip dresses in silk, satin, and velvet were also extremely popular. When Tom Ford took over Gucci in the mid-90s, his black backless and cut-out dresses quickly became collectors’ items.

Both the slip-dress and the bodycon were throwbacks to the wiggle of the 50s. Fashion does indeed repeat itself.

Shop 1990s bodycon dresses

To this day, the LBD remains an iconic fashion staple. It’s simplicity and classic style makes it the perfect choice for women of all ages and body types. As Wallis Simpson, the former Duchess of Windsor once said, “When the little black dress is right, there is nothing else to wear in its place.”

Check out my Little Black Dress Pinterest Board

Lost and Found: Vintage Swatch Clock Bag

A defining 80s fashion trend…

Swatch watches. Everyone had one, and most everyone wore more than one. We were piling on Swatch watches before jewelry stacking even became a thing. My friends and I would collect them, swap them, and borrow them based on the outfit of the day. With our teased hair, blue eyeshadow, and oversized Esprit sweaters, the right Swatch watch could make or break a look. Or so we thought.

Although everyone had the watches, few had the bag. I got the coveted rare Swatch clock bag as a Christmas present. I remember wearing it to high school after the holiday break and my classmates asking me if it really kept time. (It didn’t.)

I wore that bag everywhere in the late 1980s. I don’t remember what happened to it after I went away to college. But decades later, I was in a bar with a group of high school friends talking about old times and my friend Eric said, “One of the things I remember most about your 80s outfits is that big ass Swatch bag!” 

As a vintage fashion collector and seller, I always wondered if I would ever come across that bag again. I saw one online a few years ago, but it was sold out. And it was red, not the blue one I had back in the day. I set up all kinds of saved searches on eBay and Etsy so I could be alerted if one became available, but it never did.

As I mentioned in last week’s article, I started doing the “To Be Magnetic” manifestation program a couple of years ago. One of the exercises is to create a “mini-manifestation” list of little things you want that could be reasonably attainable in the short term (as opposed to long-term goals such as a million dollars or your perfect dream partner). The point of the mini-manifestation list to build your trust muscle. So I put the vintage Swatch bag on my list. Then I forgot about it.

A month or so later, I got a notification from eBay that someone had just listed the exact bag I had in high school. I bought it immediately. It was ridiculously expensive, but worth every penny. That’s because I wasn’t simply buying another vintage bag. I was buying back a little piece of my youth.

Shop vintage 1980s fashion trends

Vintage 80s John Richard Dress
Vintage 80s Sequin Dress
Vintage 80s Lace Collar Dress
Vintage 80s Esprit Sweater

Check out Swatch & vintage 80s clothing on Pinterest

My Obsession with Boots

It started in the 1970s. My mom had a pair of white patent leather go-go boots I wore playing dress up. As a young girl, these boots represented two things to me: power and glamour. Stepping into them, I became Wonder Woman. A Dallas Cowboys cheerleader. An Emma Sansom High School majorette. Sansom was the high school my older sisters attended, and the marching band had beautiful majorettes that were always front and center, wearing shiny sequin uniforms and glossy white knee boots. 

In fourth grade, I asked my Mom for my own pair of boots. I wanted brown or burgundy ones, not white. At that time, I wanted to dress like Chrissy, Suzanne Somers’ iconic character from “Three’s Company”. Mom took me to every shoe store in the tiny town of Gadsden, Alabama, but they were all sold out. She said she’d order a pair from the JCPenney catalog and I would have them in time for Christmas, which was just a few weeks away. But I was desperate. I wanted boots right then and there. I ended up settling for a cheap pair of boys’ boots from Payless Shoes that I thought were just tall enough to pass for the boots I’d actually wanted. 

I couldn’t wait until Monday to wear my new boots to school. I spent all day Sunday trying on clothes and putting together the perfect outfit…a striped turtleneck sweater with a brown blazer, paired with jeans that I could tuck into the boots. I was so excited about wearing them that I barely slept that night. It was just like Christmas Eve.

The next day, I marched into class confidently. Nancy Sinatra’s “These Boots Were Made for Walking” played in my head. I was so happy.  Moments later, I was humiliated. “You’re wearing boys’ boots!” the guy sitting next to me blurted out. Everyone started laughing at me. I wanted to cry, but I didn’t. I wanted to melt into my desk and disappear, but I couldn’t. At recess, I untucked my jeans. And I never wore those boots again.

Later that week, I was over at a friend’s house, and I saw a pair of tan boots next to her garbage can. I asked why she was throwing the boots away and she said they hurt her feet. She said I could have them. The boots were way too small for me and absolute torture to walk in, but I took them anyway. And I wore them for weeks.

That Christmas, I got the pair of boots I’d wanted. They were burgundy. They were beautiful. They fit perfectly. I put them on with the pajamas I was wearing that morning. I wore them all day, and I even wore them to bed that night. 

Several years later, I would once again don a pair of white patent leather knee boots when I became an Emma Sansom High School majorette. My boot story had come full circle.

Last year I started the “To Be Magnetic” manifestation program. Part of the curriculum is doing “deep imaginings” that help you go back and mentally heal childhood trauma. The first childhood wound to pop up for me during meditation was the utter humiliation I felt that day when all the kids were laughing at me for wearing boys’ boots. Thankfully, I’ve been able to heal. And now I completely understand my obsession with boots, why I can’t stop buying them, and why having a room full of them brings my inner child so much incredible joy.

A few from my current collection

Shop some of my favorite boot looks

Left: Steve Madden suede boots; vintage 1960s skirt; Rachel Comey blouse | Right: JLO Jennifer Lopez boots; Levi’s jeans; Liz Claiborne sweater; Ralph Lauren blazer

Left: Manolo Blahnik boots; Target skirt; Diane von Furstenberg blouse | Right: Guess boots; Anne Klein dress; vintage Wilson’s Leather cropped jacket

Left: Steve Madden boots; vintage 1970s peplum dress | Right: Nine West boots, Lulu’s dress; Ralph Lauren blazer

Check out my vintage story board on Pinterest

Vintage Halloween Costumes: 5 Iconic Looks

Why waste money on a cheap Halloween costume when you can invest in something you’ll wear more than once?

Just pair a knock-out vintage piece with a groovy pair of sunglasses and roll up to your Halloween party looking like a fashion icon. It’s the perfect equation for an easy Halloween costume. (1 + 1 = Boo!)

And no worries if the vintage isn’t your size. I’ve included affordable Amazon alternatives guaranteed to arrive in time for Halloween. All you have to do is choose your look.

1. Holly Golightly

Vintage 1980s Gunne Sax Black Velvet dress (available here)


2. Penny Lane from Almost Famous

Vintage 1970s faux-fur trimmed coat (author’s own)


3. Janis Joplin

Vintage floral maxi dress (sold out)


4. Marilyn Monroe

White ASOS scuba halter-dress (available here)


5. Bewitched

Vintage 1990s grommeted black maxi-dress (available here)


My Top 10 Favorite Movies for Vintage Fashion

by Sydney Stone

Whenever I need an instant mood boost, all I have to do is sit down and watch one of my favorite fashion films. I like to get lost in the vintage clothes, in the styling, and in the experiences the characters get to have in all those incredible clothes. 

The following is a list of 10 movies I love primarily for the vintage fashion. You’ve probably seen most of them. If not, add them to your watch list. If you have, watch them again. You may be inspired to organize your closet, shop for new vintage pieces, and put together some fabulous outfits to have your own adventures in.

These 10 fashion-themed movies never fail to make me happy, and sometimes even giddy.


1. The Devil Wears Prada

Duh. Everyone knows why this movie tops the list. When it comes to fashion movies, this is The Godfather. (Or perhaps The Godfather II, which I thought was better than the original.) You can stream The Devil Wears Prada here#ThatsAll

Click here to get every single look from The Devil Wears Prada

2. Sex & the City

Because Patricia Field is God and this movie (and the whole series) is the bible. Of course, Patricia Field was also the costumer designer behind The Devil Wears Prada. Because she’s God. Watch the Sex & the City movie here.

3. 13 Going on 30

The scene where Jennifer Garner “discovers” her dream closet is all of us. Bonus points for flashback 80s fashions. Watch 13 Going on 30 now.

4. Factory Girl

Edie Sedgwick is my spirit animal and Sienna Miller is a fashion icon who was born to play this role. If you’re obsessed with the sixties and all things Warhol like me, you’ll love everything about this movie. Stream it now.

Click here to get every single look from Factory Girl 

5. American Hustle

Not gonna lie. The 70s is my jam. You can find almost every single look from this movie hanging in my closet. Watch American Hustle here.

6. Bedazzled

I never thought this adorable movie got the attention it deserved. Especially for Elizabeth Hurley’s wardrobe. (And those classic 90’s eyebrows!) In this movie, the Devil wears Versace and Fendi. And she wears them well. Watch Bedazzled now.

7. Crazy Rich Asians

There is only one word to describe the clothes in this perfect film. Beautiful. Oh, and it also stars the most beautiful woman on the planet, Gemma Chan. Watch Crazy Rich Asians here.

8. Boogie Nights

This movie might not be for everyone considering the subject matter, but it’s one of my favorites. The performances, the fashion, the music…everything about this movie is just so groovy, man. Click here to get your boogie on.

9. The Breakup

Okay, we’ve always wanted Jennifer Aniston’s body. Now we want every outfit she wore in this movie. (And if you haven’t seen her kicking-ass-and-taking-names performance in The Morning Show, stop what you’re doing right now and binge every single episode.) Watch The Breakup here.

10. Clueless

Did you think I could get to the end of this list without including Clueless? As if! The most expensive shoes I have are a pair of Azzedine Alaïa leopard print sandals. Whenever someone asks me about them, I get to say in my Cher voice, “It’s like a totally important designer.” Watch Clueless now on Amazon.

Shop for vintage pieces by the decade at Shop Stylaphile Vintage!



5 Fashion Trends from Woodstock That Will Never Die

Woodstock Fashion Trends

Woodstock is the indisputable OG of music festivals. The fashion trends it spawned over fifty years ago have stood the test of time. They show up each and every year in new iterations, both on the runways and on the Instagram feeds of your favorite bloggers and influencers.

Over 400,000 people attended Woodstock in August of 1969 in Bethel, New York. It was advertised as a weekend of peace, love, and music. It quickly became one of the most influential moments in history. Hundreds of thousands of young people – dubbed “hippies” by mainstream society – proved to the world that they could gather in peace and love. And wished the world could do the same. (Yeah, that 1970s Coke commercial is playing in your head now, isn’t it?)

Woodstock influenced not only the music and the mindset of generations to come, but it also had a huge impact on the fashion industry. Many long-standing fashion trends still worn today have Woodstock to thank for their staying power.

So, in honor of peace, love, music, and fashion – here are five major trends immortalized at Woodstock that we bet you’re still wearing today.

Woodstock Fashion Trend #1: Fringe


If you search Google for photos of Woodstock, you’ll eventually come across a photo of Grace Slick wearing the most amazing white lace-up fringe top with matching bell bottoms.

Then there’s the iconic picture of Jimmy Hendrix in that white fringed shirt. Or Roger Daltry in his unbuttoned camel-colored cardigan trimmed with fringe. If you scan through photos of the crowd, you’ll see even more.

The fringe trend never goes out of style. It shows up every season on bags, shoes, boots, wraps, vests, dresses, skirts and more. There is no better way to add “it-girl” status to an outfit than with a classic fringed bag or boot.

GET THE LOOK: Be part of the fringe festival!

Woodstock Style Fringe Vest                       

Woodstock Fashion Trend #2: Boho dresses

*Rebecca Minkoff

Every fashion blogger sporting the bohemian trend at Coachella has Woodstock (and Janis Joplin) to thank for their look.

Long flowing maxi-dresses, peasant blouses and baby-doll minis in mixed prints and florals all originated in the sixties.

The boho trend seems made for outdoor concerts because it’s just so comfortable and chic. And it continues to be prevalent in modern day designers’ collections.

GET THE LOOK: When they go low, we go boho!

Woodstock Style Boho Maxi DressVintage Crochet Boho Dress Bohemian Maxi Dress Woodstock Style            Vintage Aztec Print Boho Tunic          Woodstock Style Boho Maxi Dress

Woodstock Fashion Trend #3: Halter Tops

*Alice + Olivia

Many people who attended Woodstock chose to wear as little clothing as possible. Or none at all.

For a generation of women who were into bra-burning, the halter top was probably more than just a fashion statement.

Sexy and uninhibited, the halter style neckline has actually been around since Paul Poiret in the 1920’s, and even further back to Native American culture. But Woodstock made it mainstream.

Pair a halter top with a pair of hip-hugging bell-bottom jeans and you’ll be doing Woodstock proud.

GET THE LOOK: Tie one on!

Black Halter Top                        Bohemian hippie style white halter top            71GvoSNTAIL._AC_UL640_QL65_

Black sexy strappy halter top                71oNloEK2HL._AC_UL640_QL65_                 Boho halter perfect for music festival outfit

Woodstock Fashion Trend #4: Vests

*Custo Barcelona

Fringe vests, leather vests, denim vests. They all had a showing at Woodstock. Even the guys were sporting this trend back in the day.

Like all of the trends in this post, vests can be worn year round. I’m an especially big fan of faux-fur vests for fall and winter. I have several hanging in my closet patiently waiting for the first leaf to fall in September.

Another vest trend that I’m loving right now is the super-long, lightweight duster style. They look great with jeans or leggings and can even make you look taller when worn with a pair of groovy heels.

GET THE LOOK: Invest in yourself!

Woodstock style fringe vest             vintage mesh vest          Vintage Jeanne Marc Quilted Vest        Bohemian Vest          Vintage denim vest

Woodstock Fashion Trend #5: Headbands


The best way to bring your favorite Instagram or Snapchat filter to life is to adorn yourself with a beautiful headband.

While the women of the early 60’s sported the double-wide Bridget Bardot style headbands, by 1969, the look was smaller and embellished with beading, jewels, and even flowers. (They were crowned “flower children,” remember?)

Headbands had a massive fashion resurgence moment with the CW hit show Gossip Girl as every style imaginable paraded its way up and down 5th Avenue thanks to costume designer Eric Daman.

And I have to admit, I’m wearing a headband as I write this post. Not a cute one. Just a utilitarian type taming my bed-head hair. Hey, it works. And it’s just groovy, man.

GET THE LOOK: Let it go to your head.

Boho style headband     Boho headband set      

Music Festival Flower Crown            Music Festival Flower Crown    Rose Flower Crown Headband

Want more Woodstock-inspired fashion? Check out my Pinterest board.


*Photos from

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The Devil Wears Prada Outfits

The Devil Wears Prada Montage

If you’re like me, anytime The Devil Wears Prada movie is on TV, you stop what you’re doing, you sit down, and you watch. Most of us can quote this movie word-for-word from beginning to end.

Did someone eat an onion bagel?

I’m just one stomach flu away from my goal weight.

I’m a six. Which is the new 14.

Those are just a few of my favorite Devil Wears Prada quotes.

For anyone who loves fashion, this movie is our Godfather. The Devil Wears Prada cast – Anne Hathaway, Emily Blunt, and Meryl Streep – gave us a “fly on the wall” peek into the inner workings of a major fashion magazine.

Of course, the REAL reason we can’t get enough of this movie is the fashion. Sex & the City costume designer Patricia Field waved her magic style wand again and gave us some of the most unforgettable outfits in movie history. Years later, we still want all these looks.

So whether you’re an Emily Charlton, a Miranda Priestly, or a post-makeover Andy Sachs, you’ll find all the outfits you love from the movie here along with affordable options to get each look.


Emily Blunt as Emily Charlton in The Devil Wears Prada Outfit 1




Devil Wears Prada Tassel Necklace           Devil-Wears-Prada-Style-Black-Crop-Jacket             Silver-Tassel-Necklace-The-Devil-Wears-Prada-Style

Black-Flounce-Skirt-Devil-Wears-Prada-Style           Devil-Wears-Prada-Style-Flounce-Skirt


Meryl Streep as Miranda Priestly The Devil Wears Prada Outfits 1




    Devil-Wears-Prada-style-faux-fur-coat        Devil-Wears-Prada-Style-Faux-Fur-Coat  Burgundy-Sweater-Dress

  Burgundy-Wrap-Dress           Devil-Wears-Prada-Sunglasses         Devil-Wears-Prada-Style-Sunglasses


Anne Hathaway as Andy Sachs The Devil Wears Prada Outfits 1 Chanel Boots







Emily Blunt as Emily Charlton The Devil Wears Prada Outfits 2







Meryl Streep as Miranda Priestly The Devil Wears Prada Outfits 2







Anne Hathaway as Andy Sachs The Devil Wears Prada Outfits 2 Green Coat Montage








Emily Blunt as Emily Charlton The Devil Wears Prada Outfits 3







Meryl Streep as Miranda Priestly The Devil Wears Prada Outfits 3







Anne Hathaway as Andy Sachs The Devil Wears Prada Outfits 3 Montage







Emily Blunt as Emily Charlton The Devil Wears Prada Outfits 4







Meryl Streep as Miranda Priestly The Devil Wears Prada Outfits 4







Anne Hathaway as Andy Sachs The Devil Wears Prada Outfit 4 White Coat Montage




            Devil-Wears-Prada-Style-White-Coat               41qtohg1col-_ac_ul520_sr400520_ql65_



Emily Blunt as Emily Charlton The Devil Wears Prada Outfits 5







Meryl Streep as Miranda Priestly The Devil Wears Prada Outfits 5







Anne Hathaway as Andy Sachs The Devil Wears Prada Outift 5 Montage






Anne Hathaway as Andy Sachs The Devil Wears Prada Outfits 7







Emily Blunt as Emily Charlton The Devil Wears Prada Outfits 6







Meryl Streep as Miranda Priestly The Devil Wears Prada Outfits 6







Anne Hathaway as Andy Sachs The Devil Wears Prada Outfits 8







Meryl Streep as Miranda Priestly The Devil Wears Prada Outfits 7







Anne Hathaway as Andy Sachs The Devil Wears Prada Outfits 9






Anne Hathaway as Andy Sachs The Devil Wears Prada Outfits 10 Chanel







Emily Blunt as Emily Charlton The Devil Wears Prada Outfits 7