From the Archives: 26 Vintage Treasures You Need Now, According to Jenny Walton

Few people know vintage like Jenny Walton—and even fewer wear vintage like Jenny Walton. It’s for this reason the girl about town (Milan, at the moment) has such a following. The key to pulling off her vintage looks (which span several decades) is her styling prowess. Think a vintage brooch with a modern-day Prada cashmere cardigan or a 1950s circle skirt with the latest Gucci slingbacks. But first, where is she getting these pieces? A vintage shopper rarely reveals her sources, but just for Vogue, Walton is sharing the wealth. Each month, Walton will comb through the World Wide Web and share what she feels are the best vintage buys of the moment. These are the vintage treasures you need now, according to Walton.

While I first winced at Gen Z reinvigorating the Y2K trend that as a Millennial I lived much too clearly the first time around, there have been some recent iterations that have made me reconsider my initial hesitation. Perhaps it was the prevalence of Galliano-era Dior on the Met Gala red carpet, though more realistically, my revaluation probably began with Sabrina Carpenter’s dazzling set at Coachella last month. Set against the backdrop of a baby blue Motel, the singer glided about the stage effortlessly in her feathered bangs, mini skirts, bodysuits and platform boots that felt part Y2K, part 1960s/70s dream girl. When she went viral on TikTok last week for wearing a second-hand dress from Depop for her 25th Birthday, I was inspired to take another look at the decade. Besides the similarities in shape and silhouette, I found a certain colorful optimism and embrace of technological change shared between both the late sixties/early seventies and the late nineties and early aughts. The mix of these varying decades creates a new perspective by intertwining some of the most carefree decades of fashion together and I hope you enjoy the fun mix I’ve pulled together for this month!

Happy (vintage) Shopping!

Jenny

La Perla slipThis La Perla slip of the “Malizia” line (meaning malice or mischief in Italian) is the perfect little Y2K slip dress, featuring both checks and flowers in a beautiful shade of turquoise. As Bella Hadid just proved on the Cannes red carpet, a little sheer dress can make quite the statement. I would wear this with a kitten heel in the evening or a chunky boot for the day.

Vintage spaghetti-strap party dressvintage spaghetti strap party dress

There is something so perfectly “Pretty in Pink” about this 1980’s party dress. This particular shade of bubblegum looks so fresh, light and not at all dated. Maybe it’s something about recently cutting my hair short but these Victor Costa esq. Eighties dresses have just the right amount of volume and style to make one think they too could effortlessly pull of that perfect Molly Ringwald look.

Dolce & Gabbana minidressDolce & Gabbana

mini dress

An incredible and very rare vintage Dolce and Gabbana mini dress, from the 1991 autumn winter collection (it also walked the catwalk). This is the type of stunning dress that will always “wow” in your wardrobe, despite the season or even decade, it’s timeless!

Chanel Timeless crossbody bagChanel

timeless crossbody bag

From 2002, this Vintage Chanel pink travel canvas cc logo flap bag gives that perfect Y2K feeling while still looking modern. Dress it up for a night out with a slinky chainmail Paco Rabanne dress or wear it for the day with jeans and a chic white button up blouse or simple tee.

1960’s minidressI love this true vintage 1960s cotton terry cloth pink, orange, yellow and white striped mini dress (which would make the perfect beach coverup no?) At under $100, it’s a great price for a quintessential piece of sixties fashion!

Dior one-piece swimsuitThe perfect swimsuit does not exist?! I think not!! This gorgeous John Galliano for Dior swimsuit looks to be in excellent condition (those accentuating flowers on the side?!) Pure summer perfection, that could easily be styled as a top under a flowing white pleated skirt.

Fiorucci minidressWhat really makes this little Fiorucci dress, beyond the simple and sexy cut, is the sexy back detail. wonderfully naked, the line is tight, just flared at the bottom. Small suspenders in elastic lace, A great example of Y2K fashion that could be easily dressed up or down.

Betsey Johnson Daisy Duke shortsBetsey Johnson

Daisy Duke shorts

I used to make my mom drive to the King of Prussia mall in Pennsylvania (we lived in New Jersey), specifically for the Betsey Johnson boutique, which at 16, was my idea of ruffled heaven. I love these pink gingham Betsey Johnson “Daisy Duke” shorts (how cute were they originally styled on the runway with that sheer blue top and rockstar “i don’t give a damn” styling!?)

Dior Saddle vintage cloth handbagDior

saddle vintage cloth handbag

The quintessential early aughts bag, the Dior saddle bag which has seen a resurgence in recent years. Some say it was first inspired by a Helmut Newton photo from 1976 entitled “Saddle 1, Paris.” To me, if you’re going to lean into the Y2K trend and wear, let’s say a mini silk slip dress, there is no better accessory than this printed Dior saddle bag.

Versace 1990’s minidressI love this fantastic 1990’s Versace vintage pink mini dress with its whimsical bustier and Barbie hot pink tone. It has just the right amount of tension, with it’s pointed edges and sleek silhouette.

Valentino Garavani leather heelsValentino Garavani

leather heels

These Valentino Garavani platform pumps (never worn by the way) are the perfect Sabrina Carpenter accessory. Versace made a similar platform heel and there are several unworn pairs of each currently on Vestiaire – ready to take your style to new heights this summer – literally!

Moschino minidressA great vintage Moschino Cheap and Chic 90’s yellow dress featuring a halter neckline and fabric-covered buttons. I find this type of dress to be a great go to as you can style it for so many different occasions and instead of your typical black dress this shade of yellow is just enough to “pop” without feeling too jarring.

Twiggy top-handle toteThere is nothing I love quite like a vintage doll carrying case (I had some of my mother’s Barbie vinyl cases from the 1960’s when I was growing up) and the fact that this one is Twiggy and made by Mattel makes it even better. Originally from 1967 I would use this as a great little purse / conversation starter.

Floral chiffon nightieBetty Draper could never (just kidding she totally would). Yes, you could lounge around your house in a tank top and sweatpants…OR, you could buy this fabulous little vintage 1960s baby doll nightgown and have your neighbors saying “did you SEE how chic Kaitlyn in 4B was when she was getting her package?!” Get ready to clear your schedule as you’ll be invited to every dinner party in your building for the foreseeable future.

Honey Hole upcycled floral halter topHoney Hole

upcycled floral halter top

I love this simple halterneck top that has been upcycled from a vintage tablecloth (what a great idea, no?) The self tie options at waist and neck allows the top to fit a range of sizes from small to XL. This would pair perfectly with a pair of high-waisted capri’s or a great fifties circle skirt.

Chanel swim setThe perfect Chanel swim set that looks so Barbie, I’m surprised Margot Robbie didn’t wear it on her press tour. From the Spring Summer 1993 – 1994 collection this would be the perfect summer set for all of your chicest of travels.

Terry de Havilland Glitter Stardust heelsTerry de Havilland

glitter stardust heels

The one and only ‘Rock n Roll cobbler of the 1970s’ and worn by the likes of Bianca Jagger, these Terry de Havilland black and silver sparkle ‘Stardust’ heels date back from the early seventies. The perfect party shoe and just as classic today as it was when it was first designed!

Betsey Johnson minidressThis cute little vintage Betsey Johnson light blue princess style dress with pink tulle petticoat makes me want to go to Homecoming all over again. Add a microphone and an espresso martini and your Sabrina Carpenter Halloweed costume is SET.

Victoria’s Secret silk slip minidressVictoria’s Secret

silk slip mini dress

I own several vintage early aughts Victoria’s Secret slip dresses and I have to say, they do the trick (and can often be found at great price points). I love this shade of pink but what really makes this dress is the criss cross low back that makes this piece just a little too special to only keep to the bedroom.

Balenciaga City leather handbagBalenciaga

city leather handbag

The revival of the Balenciaga City bag comes with the fact that…you should just buy a vintage Balenciaga City bag. I love this weathered shade of pink which perfectly compliments the roughed up motorcycle look.

Saint Laurent Flamenco evening dressSaint Laurent

flamenco evening dress

An iconic Yves Saint Laurent Autumn-Winter 1987 black lace flamenco evening dress that I could imagine the likes of Stevie Nicks wearing or even someone like Sabrina Carpenter on a moodier day. Either way this dress would be sure to bring out your inner singer / performer!

Chanel 1995 piqué halter dressChanel

1995 piqué halter dress

A stunning Chanel Spring Summer 1995 rare piqué halter dress by Karl Lagerfeld and seen beautifully on the runway above. The styling of this piece on the runway is a great example of how great accessories can take something as simple as a little black dress from wow to HOW?!

Paco Rabanne glitter mid-length dressThe perfect Paco Rabanne vintage silver dress in metal mesh. This is a dress that despite its sparkle, will remain absolutely timeless for decades to come. I would wear it with a small vintage lucite clutch and a great pair of clear heels for a more modern look.

Blumarine minidressA great little Anna Molinari for Blumarine dress from the nineties but in the style of the sixties (very Priscilla Presley as the listing proclaims). At around $150 this is a great price for a timeless vintage dress!

Paco Rabanne glitter topAnother incredible piece from Paco Rabanne this top features a mix of gold and silver metal sequins in the shape of hearts. In my opinion, these iconic Paco Rabanne pieces will only increase in value over time, making them a great investment (and this piece has never been worn, which is even better).

Dior satin high-slit gownWhile on the higher end of the budget this stunning 2003 John Galliano for Dior is just too stunning not to include. From the Fall Winter 2003 collection, this pink silk satin gown is just the type of Galliano for Dior dress that every collector dreams of (and I love the surprise deep V in the back!)

AprilOh, what a wonderful time of year for dressing! Once April comes along nothing makes me happier than changing over my wardrobe and rediscovering all of the color, print, and novelty that is usually hidden away during the colder months. Even if April is still a bit rainy, I love getting excited for May and June by pulling my summer dresses out of storage and letting myself begin to dream about warm nights having aperitivo and a crisp Campari Spritz with friends.

While in Venice for the Biennale this past weekend I wandered, as I often do, into the Miu Miu and Prada boutiques which are absolutely filled with florals at the moment. While I do occasionally indulge in the special piece, I often use these store visits as inspiration, and afterwards will head home with a whole new list of vintage search terms in my head, to try and recreate the great new fashions (in a manner just slightly more economical). At Miu Miu, I fell in love with a beautiful silk chiffon floral print halter dress featured in the new Gigi Hadid campaign, and now all I want are little floral dresses and cropped cashmere cardigans. Sue me! I can’t help it—they’re just adorable!

While quite hard to come by these days, a wonderful little floral-print spring dress used to be the norm and therefore our favorite vintage sites such as Etsy are chock-full of them (with price points often quite close to that of a Reformation dress, if not less). As is always the benefit with vintage, the likelihood that someone else is going to arrive at an event this spring in the same look as you, is close to zero. And nothing beats being able to say “oh this old thing…vintage!” That is to say, “You can’t have it!”

Happy Shopping!

Jenny

Sea of Vintage 1950s dance dressSea of Vintage

1950s dance dress

Now this is a show stopping, everyone turn-their-heads-when-you-walk-in-the-room kind of dress. While it’s a great silhouette for a curvier shape, the panels jutting out from the bodice can also create a great illusion for those of us with a little bit less oomph on the top half. I’m simply in love with this crisp white and bubblegum pink and I’ve never seen a dress quite like this one so snap it up fast!

Victor Costa backless evening dressVictor Costa

backless evening dress

No one, and I mean no one, made a dress quite like Victor Costa in the 1980s. He had this incredible knack for recreating 1950s silhouettes in a slightly updated manner without giving into too many stereotypically 80s trends (although he did do the occasional puff-sleeve dress, to which I typically politely say, no thank you). I own this same dress in a red and white stripe and can confirm that this is one of the most exquisitely-shaped dresses of all time.

Miu Miu 2018 long dressI love this 1960s/1970s-inspired Miu Miu dress from 2018. It’s exactly what I want to wear all summer long with a great pair of easy T-strap sandals and a raffia tote bag. This is a standout floral print that somehow does not overwhelm despite the boldness of the color. Please, someone buy it before I do.

Prada Spring/Summer 2011 striped dressPrada

Spring/Summer 2011 striped dress

From a quintessential summer Prada collection, spring/summer 2011, this is a simply stunning striped dress. In addition to this look walking the runway, you may remember that Scarlett Johansson also wore it on the red carpet at the Cannes Film Festival last year. I have multiple dresses from this season, including a dark blue version of this silhouette and can attest that they are wardrobe staples.

Vintage Midi-DressAn absolutely stunning unbranded vintage 1950s dress (with a very chic exposed back!). This is the type of little black dress you want in your wardrobe as a constant go-to. I would wear it with a chic little black kitten heel and vintage black clutch.

Prada midi-dressPrada 2012 is another great season to look at for colorful spring dressing ideas. The 1950s inspired candy-colored collection looks just as fresh over ten years later and this stunning colorway is quite unique and much more difficult to find than the blue white and gray version that you typically see on resale sites.

Cole of California halter dressCole of California

halter dress

This shade of blue is simply divine. If I saw someone wearing this on the street, a double take would be guaranteed. It’s Cole of California from the late 1940s/early 50s and reminds me of something Grace Kelly would have floated around in Rear Window as James Stewart looked on with his jaw on the floor.

Nos 1950s cotton dressAnother timeless dress is this beautiful 1950s cotton gingham day dress. I find that sun dresses designed these days often have too many extraneous details, or the neckline is too low, or they add an unnecessary and uncomfortable sky-high slit (can’t a girl just sit in peace?). I love something about the simplicity of this vintage dress, it’s quite old and yet looks unexpectedly fresh to me.

Vintage Vavavoomz 1950s pleated sundressVintage Vavavoomz

1950s pleated sundress

If you’re in the market for a great spring/summer dress you need not look further than the fabulous Etsy shop of Vintage VaVaVoomz. I’ve bought several pieces from her wonderful archive and I never regret a purchase. This striking striped 1950s sundress features some of the most beautifully-pleated stripes that I’ve seen. A truly one-of-a-kind piece!

Create and Collected 1950s raffia dressCreate and Collected

1950s raffia dress

A few years ago, I purchased one of these great 1950s/60s crocheted raffia wiggle dresses in pink and it’s one of my go to spring looks! This black and silver version is simply stunning and will be a classic in your wardrobe for years as it’s simply impossible to go out of style because it is style!

Charles Warner 1940s vintage dressCharles Warner

1940s vintage dress

This 1940s vintage dress by Charles Warner featuring a mesh panel collar and bow detailing would make Joan P. Holloway Harris simply faint (and of course subsequently, Roger). I’ve never seen such a beautifully delicate neckline on such a great and wearable little dress. Everyone will want to know where it’s from.

Vera Mode 1950s chiffon dressVera Mode

1950s chiffon dress

Perhaps it’s because I was just in Arles and immersing myself in the wonderful world of Van Gogh but this painterly 1950s chiffon party dress seems to hit just the right note. That daring yellow brings just the right pop of color to push your winter wardrobe into nothing but a distant memory.

Victor Costa strapless dressVictor Costa

strapless dress

If you do nothing else today, click the link to see the stunning construction of the underskirt on this beautiful 1980s does 1950s Victor Costa show stopper. Because of its simplistic perfection, this dress can be worn in just about a million different iterations.

Victor Costa vintage polka dot dressVictor Costa

vintage polka dot dress

One more vintage Victor Costa dress, because they are just simply too good to not collectively drool over! I love this polka dot party dress (with an unexpected beautifully low back). I think of Molly Ringwald in the 1980s wearing something fabulous like this and it makes me want it even more.

Bill Blass vintage mini dressBill Blass

vintage mini dress

This is a great little Bill Blass dress from the 1960s. I’m especially in love with this colorful pink floral print which offers so many great options when selecting which colorful pair of shoes to pair it with. Alternatively, this would look great styled with a pair of Church’s x Miu Miu brogues (look to the Miu Miu fall/winter 2024 runway for some great inspiration on how to style it).

1920s vintage silk chiffon dress1920s vintage silk chiffon dress

Many 1920s flapper dresses can often have a bit of a dated look to them or are often in poor condition. I love this little black chiffon flapper dress with its matching rhinestone belt. It looks surprisingly modern for its age, as if it could be seen on a current Chanel runway. Perhaps it’s something about the last Miu Miu show that is still sticking with me but I envision this looking so cool and modern with a menswear-inspired brogue and a chic chopped hairdo.

Betty Jo Vintage 1960s floral dressBetty Jo Vintage

1960s floral dress

A perfect 1950s pink floral dress (with a beautiful detail at the bust). I typically try not to match my clothing too closely to my makeup but I can’t help but envisioning this with a beautiful raspberry lip. At only $90, this one is a steal.

JJS Hoard 1950s bolero dressJJS Hoard

1950s bolero dress

This is one of the best fabrics I’ve seen all year. So unique and such a strong and beautiful color combination of the blue and yellows. I love that this dress still has its matching bolero, which you could have fun mixing and matching with other pieces in your wardrobe such as a pair of jeans or a solid blue or black skirt.

Opulent Textiles vintage sheer silk chiffon day dressOpulent Textiles

vintage sheer silk chiffon day dress

This is such a beautiful 1930s dress. It looks like something Ralph Lauren would buy just to have in the archive, if not reproduce exactly as seen here. I’m a firm believer that everyone should collect things from varying decades in their wardrobe, in order to provide some variety (and because I like to think of my wardrobe as a mini museum). This bias cut sheer chiffon floral dress is a perfect representation of the beauty of 1930s fashion (not to mention it was recently deaccessioned from the Strong Museum in Rochester, NY, so it quite literally is museum-worthy).

Simplicity Is Bliss vintage 1950s floral dressSimplicity Is Bliss

vintage 1950s floral dress

Such a modern seeming vintage 1950s floral wiggle dress in a beautiful shimmering blue and yellow fabric. This vintage dress features an outstanding fitted bodice with a wonderful V-neckline, nipped waist, and pencil skirt.

Fred Perlberg vintage 1950s halter dressFred Perlberg

vintage 1950s halter dress

This is such a timeless dress and I love the subtle monochromatic cording detail set against two rows of black ribbon. A great first date dress if you want it to be your last first date ever!

Arnold Scaasi vintage midi-dressArnold Scaasi

vintage midi-dress

A brilliant color combination from designer to the stars and First Ladies, Arnold Scaasi. This late 1970s/early 80s dress would look so stunning with a Molly Ringwald à la The Breakfast Club hairdo, and a pair of great loafers.

MarchChapeaux à Panache!

There are few things as fabulous as a funny hat; you need to look no further than The Row’s highly anticipated Resort 2025 collection for confirmation of this wonderful sartorial truth.

Now if you’re going to have personal style, you need a healthy dose of panache, and panache is what I mean when I say funny. A hat with a wink.

Hats used to be an incredibly popular thing to wear (just try searching “vintage 1950s hat” on Etsy and see if you come up for air in about a week). In recent years, however, hats seem to have gone the way of the dodo, and along with our chicest of accessories (the gloves and the brooch), have become lost to the wind of ever-changing style. Yes, we have the baseball cap and the beanie, but besides the occasional outlandishly oversized pom pom, they don’t bring that extra oomph of personality and importance that hats once held. Some of the most prestigious couturiers, Coco Chanel and Jeanne Lanvin, both began their respective careers as milliners. That’s why it’s such a delight to see the grand return of hats to the runways this season at The Row, Altuzarra, Jil Sander, Prada, and more.

The only problem? You probably don’t want to wait six months nor is it favorable to pay into the thousands of dollars for a singular quirky hat. Well that’s where I come in. I’ve selected 34 hats for under $500, with most falling around the $50-100 mark. A hat adds instant personality to a look and in a time when the personal seems to be missing in style, why not add a chic chapeau into your wardrobe’s repertoire?

Happy Shopping!

Jenny

1930s Red Felt Hat with BowsI don’t often use the word darling, but this hat has such an inherent sweetness that it seems to justifiably warrant a vocabulary akin to that of your great aunt Edith. It’s hard to find the perfect shape and color in one hat but by god Edith, we’ve done it this time!

Black Triangular HatIn addition to meaning confident style, the historical definition of panache involved adding an advantageous plume to your hat, so if we’re talking panache, this one is currently batting a hundred.

Sheryl’s

vintage triangular hat

Vincent & Harmik Mink HatI recently purchased a vintage fur beret, and before my dog discovered and mistakenly identified it as an intruder that needed a quite tough “roughening up”, we were inseparable. After leaving hat hospital, my chapeau is as good as new, and when we’re not taking the town by storm, she sits happily on a very high shelf.

Vincent & Harmik

vintage 1960s hat

Vintage Black Wool HatI could see Coco Chanel or any other equally chic icon of style, strolling along the Seine in this beautiful bowed chapeau. As Chanel did herself in the 1930s, this piece could easily be modernized with a great pair of long black trousers and a great little knit.

Driving Hair CoverThis is exactly what a Hitchcock blonde would have worn to the chicest funeral of her LIFE. Imagine zipping around in your convertible, completely unbothered as your hair will be just as perfect upon arrival at your presumably very chic destination.

Rockabilly

50s 60s driving hair cover

Mr Herbert Black Velvet Round Trailing Grosgrain Ribbon Bow HatWith a certain ecclesiastical air about her, this wide-brimmed beauty could easily work in on Sunday or any day of the week for that matter. Anything with a billowing bow is pure class, in my opinion.

Mr Herbert

50s velvet bow hat

Christian Dior Miss Dior Brigitte HatDoesn’t this perfect shade of turquoise just make you want to get up and get dressed? What you pair it with won’t really matter, as this vintage Miss Dior hat is just perfectly pretty even by itself.

Dior

1950s Miss Dior Brigitte hat

Miss Dior By Christian Dior Cap Cloche HatMarch can be famously cold, so it’s still not too late to snag up a wonderfully furry winter hat. Plus, this Miss Dior beauty is destined for style greatness a.k.a she’s too classic to go out of style.

Dior

50s Miss Dior cloche cap

Philippe Model Vintage 1980s Avant Garde Black Wool Bow HatNow this is a fabulous hat. To warrant an adjective like fabulous, the hat must have that EXTRA special OOMPH. And boy does she have it. Plus, you’d be the chicest person at Disney, if you’re into that sort of thing.

Philippe Model

1980s Avant Garde bow hat

Red Knit Cloche Brim HatThe only thing chicer than a great red hat, is a great red hat that comes with a built-in scarf! That pop of red has been a big trend so far this year, but so far we’ve mainly seen it in sock form. I think it’s time we brought the trend a bit north no?

Turban Twist HatIf you’re looking for a cost effective way to replicate The Row, look no further. This stunning hat has that perfect touch of Panache. Look at their newest Resort 2025 lookbook, shot by the amazing Jamie Hawkesworth, for endless styling inspiration.

Etsy

1930s turban twist hat

Turban-Style HatThe beautiful bow at the back of this vintage turban style hat, can easily be adjusted to fit your stylistic needs. I love the idea of wearing this very casually, with a wonderful bateau neckline ivory silk top and flowing silk ivory pants.

Vintage 1940s HatSuch a beautiful vintage hat with a great combination of wonderful wool felt knots and trimmed in stunning little wool bows. A piece that stands out, without having to scream, is often the best and can be worn time and time again.

Velvet Pixie HatIf you’re looking for a The Row Penelope hat dupe, this is your girl. A wonderful little knot tops this perfect chapeau. Classic, beautiful design at it’s best with just a touch of flair.

Beaded Helmet HatI simply love this beaded bonet by Mr Milton for Marshall Field. It’s rare to find a vintage hat with so much character and still in such great condition (not to mention a great price). Think of how chic she’d look peaking out under the brim of your favorite cashmere hoodie.

Mr Milton

1960s beaded helmet hat

Golden Straw Lace Cloche HatI’ve never seen a vintage hat quite like this (and trust me, I’ve seen my fair share of fabulous headwear). I could see this hat working beautifully on a vacation to the French Riviera.

Etsy

1920s golden straw lace cloche hat

Vintage Antenna Fur Rhinestone HatThis hat is simply divine. Slightly higher on the price list, but still less than half of what a new hat from one of the top designers might run you these days – not to mention no one else will have this one! I love the fiery spires of its fabulous peak, paired with the stunning oddity of the two dangling rhinestones. 10/10!

1stDibs

1960s antenna rhinestone hat

Yves Saint Laurent Vintage Felted ClocheProving that clowncore is nothing new, this fabulous Yves Saint Laurent cloche is an absolute steal for a piece of fashion history. And in the end, it reminds me of Pierrot and just makes me smile.

Saint Laurent

vintage felted wool cloche

Prada Wool HatThis fantastic AW 2005 beret from Prada is a stunningly chic update on a classic. While technically one year away from being officially vintage (anything 20 years or older), she looks as modern today as when she first appeared on the runway.

Hermès Bucket HatThe high crown of this classic corduroy hat from Hermes gives it just that extra special touch of style. One of my favorite parts about living in Milan is seeing all of the, what I call, “old man corduroy” (essentially chic old men, who wear beautiful corduroy). Paired with my own pair of “old man cords” I’d give them a sartorial run for their money with this beauty.

Hermès

corduroy bucket hat

Pixie Wool HatI can name at least five designers who I bet wished they found this vintage treasure while designing their latest collections. The listing mentions that it’s rather small and might need to be placed with the help of a hair pin. Which is what I call, a shopping opportunity.

Christine Original Brown Sequined HatRich brown felt with a deep brown grosgrain ribbon AND layered sequins? What more could you ask for?

Etsy

1960s Christine sequined hat

Sally Victor Feather HatI honestly have no idea what’s going on here…and that’s exactly why I love it. A fantastic fur felt hat with feather and yarn accents designed by Sally Victor and labeled for Meier and Frank in Portland, Oregon. It was made circa 1945 and the listing says that it’s still in very good condition which, considering that this looks like something out of a cat’s most passionate fever dream, is kind of a miracle.

Sally Victor

1950s feather hat

1950s Raffia Woven Beehive Turban HatMade entirely of raffia and velvet, this beehive-style turban from the 1950/’60s is most certainly a unique head-turner. Personally, I love when raffia is used in interesting and different ways, and think this is such a unique take on the typical beehive/turban shape you often see from this period.

Etsy

raffia woven turban hat

New York Creation Mini Top HatThis particularly chic chapeau has an equally alluring history. It was created by The New York Creation label, which encompassed a group of designers who joined together to promote New York fashion. Vintage Fashion Guild says: “The New York Dress Institute was formed in 1941 as a joint venture between the clothing manufacturers of New York City and the ILGWU. Under the leadership of fashion publicist Eleanor Lambert, Its purpose was to advance the sales of dresses and clothing made in New York by promoting the city as the fashion center of the country.”

I love that the listing describes this 1940’s hat as “jaunty.” Just the right word for a beautiful hat with a positive character.

New York Creation

1940s mini top hat

Two Tone Brown HatThis is a beautiful vintage 1940s/1950s two-tone brown woven straw hat. The listing mentions that it is meant to sit on top of the head and is best secured with a hat pin. I love the two tones of brown, which give this vintage hat an unexpected freshness.

Pink Pillbox HatBows, beads and mesh?! For $29, the price is most certainly right on this gorgeous 1950s pillbox hat. In a perfect dusty pink shade that would make Miu Miu jealous.

Mr. John TurbanA rarity in the vintage world, tags are still attached! Be the first to wear this beautiful golden 1950s / ’60s turban. I love the asymmetrical shape of this one-of-a-kind piece.

Mr. John

vintage classic turban

Prada Patterned Wide Brim HatWith the arrival of Chanel’s new Deauville-inspired Fall-Winter 2024 collection comes the return of the wide-brim hat. It’s a perfect opportunity to jump on the trend in a sustainable way with this Prada orange and black striped cotton wide brim hat from the iconic Josephine Baker-inspired Spring-Summer 2011 collection.

Prada

patterned wide brim hat

Pompilio Wool HatThere is a stunning modernity to this black cloche by hat designer Elvis Pomplio of Brussels, Belgium. I love the idea of wearing it with a chic drop-waist black dress and mary janes.

Mr Roberts Floral Fruit HatThis is probably one of the most unique hats that I have ever seen (and that’s saying something). I love the frosted velvet fruit and flowers and the emerald green color of the base.

Mr Roberts

floral fruit hat

Christian Dior Basket Weave Turban BeretI bet Bottega Veneta wishes they thought of this one. A beautiful basket weave pattern to this stunning 1960s slouched beret by Christian Dior. And for only $151, are you kidding me?

Christian Dior

basket weave turban beret

Black Fur Crocheted ClocheThe fantastic thing about this vintage black fur cloche style hat (likely from the ’30s or ’40s) is that at first glance, it looks as though you’ve spent hours shaping your hair into beautiful finger waves). A stunning, truly one-of-a-kind piece that would look sensational with a nineteen twenties shift.

Navy Felt Cone HatAs this mannequin demonstrates, if one eyebrow isn’t permanently raised, then you’re wearing this hat, all, wrong. Equal parts witchy and devilishly smart, this is a hat for a woman who knows what she wants and knows her style.