Equally serving, is its ability to add an instant injection of fun into your wardrobe. It’s a place to indulge yourself, take risks, and get a little…weird. With Halloween comes the perfect opportunity to dive into this eccentric world.
Albeit more lighthearted than the holidays that follow, Halloween kicks off the season, and what I’m usually craving this time of year is something with a bit of a twist to it. I don’t want it to be too serious – I want to wear it with a wink. Whether that be a Moschino Couture suit with Ed Ruscha-esque cursive “Secrets” and “Desire” embroidered across its hemlines or a Gaultier dress that quite literally transforms you into a goddess, why not this season use fashion as an icebreaker?
That’s why this month I’ve hunted down items with a bit of a surrealist spin to them, trompe l’oeil galore! As someone who carried around a plastic pigeon as a purse the majority of last year, trust me, you will have fun and make new friends, absolutely…everywhere you go.
As is always advisable with vintage, if you like it, snag it! There is only one after all. Take a moment to view the measurements, which should typically be provided as vintage sizing is inconsistent. A good general rule is if it’s too big, you can always have it tailored to you. However, I try not to alter the iconic pieces too much, as I do view them as works of art (and altering them can hurt their value).
Happy Shopping!
Baci, Jenny
Moschino Couture Eyes Bustier (circa 1990)
With this top, you will finally be able to confound men by saying, “Hey! My eyes are down here!” It will be your perfect opening line, so buy this top before I do, because god, am I tempted (for the conversational aspects alone). Fashion, as an ice breaker, is fashion in its highest form (this coming from the woman who bought the Pigeon purse…naturally).
Silk Chiffon Beaded Dress (circa 1920s)
An absolute steal for this 1920s trompe l’oeil beaded dress (you try looking this fresh after one hundred years). Endlessly chic. Consider cutting your hair into a bob shortly after purchase.
1stDibs
chiffon beaded dress
Jean Paul Gaultier Graffiti Goddess Dress (circa 1999)
Newly added to sale (40% off and god knows why), this iconic piece by Jean Paul Gaultier is sure to fly off the metaphorical rack. One of these is currently in the collection of the V&A Museum…now isn’t that more enticing than, say…a new season D&G?
Jean Paul Gaultier
graffiti goddess dress
Prada Tromp L’oeil Pleated Skirt (circa 2004)
It’s hard to give you all the good links, and yet here I am, doing just that. These iconic Prada pieces are so hard to find. Seems to be in very good condition and despite being almost 20 years old, it looks as modern as ever. Would wear it immediately with a black knit and kitten heels (Prada, of course).
Prada
Tromp L’Oeil pleated skirt
Comme Des Garçons Iconic Lumps and Bumps Top and Skirt Set (circa 1997)
If you want to own a piece of fashion history, well park your car right here. I love this ensemble for the fall. It’s the perfect mix of colorful and subdued. Not to mention that crisscrossing red gingham has the fabulous visuality of acidic red spiderwebs. Spooky indeed!
Comme des Garçons
iconic lumps and bumps set
Vintage Floral Printed Dress (circa 1950s)
A perfect fall palette and a great price to look like you just walked out of a Hitchcock film. Not to mention there’s something just the right amount of twisted about a sour green rose.
1stDibs
floral printed dress
Jean Paul Gaultier Jeans Printed Trompe L’Oeil Skirt (circa 1990s)
You know those days when you can’t decide if you want to wear jeans or a skirt? Well consider your incredibly weighty problems, solved.
Jean Paul Gaultier
printed Trompe L’Oeil skirt
Gianfranco Ferré Leather Gloves with Fringe
If you don’t add these to your scarecrow costume, what are you doing? Don’t let them sit in a box for one more Halloween, dear god please! Good fashion deserves to be worn. And by the genius Gianfranco Ferré, these are just too good to pass up.
Gianfranco Ferré
leather gloves with fringe
Sonia Rykiel Navy Knit Dress with Trompe L’Oeil Diamanté
I just love this easy knit dress with the chicest glittering trompe l’oeil diamanté. So easy to dress up or down and because it’s knit, less restrictive than most vintage. People will constantly stop to ask you where it’s from to which you can effortlessly answer “vintage darling, vintage.”
Moschino Couture Embroidered Words Top and Skirt
I saw this fantastic set after going to the Ed Ruscha retrospective at the MoMA and it reminded me so much of his fabulous “word” paintings that I’ve been thinking about it ever since.
Moschino
embroidered words top and skirt
Schiaparelli Diamante Spider Necklace
If this doesn’t perfectly sum up October, then I don’t know what would. It’s perfect in every way and would wear effortlessly with a little black dress.
Schiaparelli
spider necklace
Marc Jacobs Black Waxed Satin Dress
It’s such a great moment to be on the lookout for old Marc Jacobs pieces, as I believe their value will greatly increase over time. I love the trompe l’oeil effect of the pleated netted tulle along the hem. So delicate and charming.
Marc Jacobs
waxed satin dress
Bob Mackie Vintage Dress (Circa 1980’s)
This is another case of “if you don’t buy this I will.” Vintage Bob Mackie?! 80% off?! A perfect party dress to carry you through all of your upcoming festivities. Would look great with a black pump and some pearls. If you need inspiration, put on Whit Stillman’s Metropolitan (1990).
Halston Vintage Long Dress (circa late 70s – early 80s)
There are few things chicer than showing up just about anywhere in a vintage Halston dress. But add some Elsa Peretti adornments and you’ll be the talk of the town. Side note, imagine how much you can eat in this thing!
Halston
vintage long dress
Marc Jacobs Sequin Top Handle Bag (circa 2010)
An incredible deal (I’ve seen these bags go for as much as $1,500). Not to mention it’s from one of my personal favorite Marc Jacobs collections—Fall 2010. Look at the show for inspiration on how to wear her, but I would suggest sumptuous wool and cashmere coats in varying shades of gray to really make those glittering sequins pop!
Marc Jacobs
sequin top handle bag
Marc Jacobs Striped Long Dress
Rarely has there been such a divine time to shop Marc Jacobs. The clothes themselves are of wonderful value and yet their resale value seems to be at a historic low. But we’re not playing the short game are we? No! We’re fashion lovers, and we’re in it for the long haul. What goes down must come up, and I’m sure the value of these pieces will rise once again (but enjoy the prices now while you can!)
Marc Jacobs
striped long dress
Jean Paul Gaultier Trompe L’Oeil Sheer Tuxedo Print Dress (Circa FW 1996)
A truly iconic look from Gaultier, that quite literally says, business in the front, party in the back.
Jean Paul Gaultier
sheer tuxedo print dress
Dries Van Noten “Top?”
There are few things in life as delicious as a Dries Van Noten purchase. While I’m not completely convinced that this is a top—The Real Real has been known to make mistakes; I once bought a yellow beaded Dries Shawl that was labeled as a belt*—*does that really matter? Wear it how you like! That’s the fun of fashion anyway.
Unbranded Knee-Length Dress
If this dress was Prada, it would easily be $2,000. That’s why I love buying unbranded vintage when it comes to the embellished, embroidered, etc. This would work so well for “that fun party dress” to have in your closet. Transform it every time you wear it by changing up your hair, makeup, etc. (I would wear with a block cloche and a long string of pearls.)
Unbranded
knee-length dress
Prada Embroidered Silk Coat (circa 2012)
Although originally from a spring collection, to me this coat has the perfect fall palette. Such a standout piece. It was recently listed and I’ve never seen this colorway for sale before (much more common is the slate gray CC with white and periwinkle embroidery).
Prada
embroidered silk coat
Christian Dior by Marc Bohan Satin Pleated Feather Turban (circa 1960s)
People are decidedly not having enough fun with hats. What fun people used to have with hats! And some designers are trying (The Row’s recent forays, although minimal, come to mind). Marc Bohan for Dior is the crème de la crème of hat history, so it’s worth the splurge to have a part of fashion history in your wardrobe. Go on! Have some fun.
Dior
satin pleated feather turban
Prada Runway Dress (circa 2007)
From one of the best collections of all time (I have it in green, in the suit version). These pieces often fetch closer to $1,500 so it’s a great price for an iconic piece from arguably the greatest designer of our time. Would look great with a croc-embossed kitten heel or a good boot.
Marc Jacobs for Louis Vuitton Sequin Speedy (circa 2012)
I’ve been predicting the return of the speedy in a big way, for a few months now. I think they’ll be gaining a lot of traction this year, particularly with Pharrell as the newly appointed men’s creative director (Jonathan Anderson recently posted a green printed speedy by Pharrell) Personally, I would opt for one of the very special ones that Marc Jacobs created for the brand, such as the sequin example below.
Marc Jacobs
sequin speedy bag
Stella McCartney Banana Top for Chloe (circa 2001)
It’s hard to find basics that have that artistic edge to them. I’m currently reading Charlie Porter’s What Artists Wear and was reading the chapter about Sarah Lucas and her “Self Portrait with Fried Eggs” and I saw this top on Vestiaire on the same day. Felt like fate! Someone should snag it up.
Stella McCartney
banana top
Jean Paul Gaultier Pareo
Rarely do you find a masterclass in styling, in the way these photos show (bravo to the private seller who uploaded them all!) A great value for how many looks you can get out of this piece, I love that you can add your own personality to it depending on how you wear it.
Prada Gold Skirt
If you want to be ahead of the curve, Miu Miu essentially just showed this skirt a few weeks ago, well now you can have the original.
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