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Welcome to Addressed, a weekly column where we, ahem, address the joys (and tribulations!) of getting dressed. So far, we’ve unpacked how to wear shorts at the office and beyond, how to pack a carry-on bag for a work trip, how to dress with style in your third trimester, and even how to layer without looking like that chair in your room (you know the one). Download the Vogue app, and find our Style Advice section to submit your question.
Last week, we posted an open call on the Vogue app, asking users to share photos of vintage pieces in their closet that they haven’t figured out how to wear. It’s an unfortunately familiar scenario: We find our dream vintage pieces on eBay or at a thrift shop only to get home and realize the fantasy version of us isn’t quite squaring away with who we are in real life. Our group chat was filled with images of opulent ’80s jackets, Y2K It bags, and assorted denim separates, all ripe for experimentation. Although members of our community were quick to jump in with their own styling advice, here’s our take on your queries.
The Vintage Suit
User @breatheplayroar shared a photo of a fabulous short-sleeve heart-print YSL suit. I’ve found a few vintage suits in my life, and what I love about them—and the reason why I’ll let myself splurge a little if necessary—is because you can break them up and have them pull double (or triple?) duty in your wardrobe. But let’s start with the whole thing before getting into the sum of its parts. Another Vogue app user suggested the suit be styled with a pair of black tights and white pumps, which was exactly my instinct because it’s an interpretation of how the suit might’ve been worn in its own time—though I think the trick to actually make it modern would be to subvert those same notions by slightly altering the components. Instead of semi-sheer black hose, try heavy opaque black (or navy!) tights paired with a shoe that feels more contemporary—like Jil Sander’s odd little point-toe Mary Jane, or even crackled silver tabi pumps.
I also like the idea of breaking up the suit and pairing it with ultralight knit pieces: the short-sleeve jacket with a pair of bright red bike shorts and ultraslim sneakers or classic Repetto ballet flats; or the skirt paired with an oversized polo in grey or black and these truly cuckoo Alaia flip-flop/mule hybrids. It’s almost like you want to deflate the history that goes with a vintage YSL suit from the time.
The Vintage Jacket
Many users shared images of vintage jackets, and my mind immediately went to the recent Valentino collections, where Alessandro Michele so expertly paired very prim and proper jackets with casual straight-leg jeans—which can then be dressed up or down with something very femme, like a kitten heel, or something more grounded, like a pair of streamlined sneakers (I am always partial to a pair of white or off-white high-top Converse).
The Y2K Skirt
@kesaria has a super cool vintage denim skirt made with a trompe l’oeil deconstructed look—which was all the rage in the early 2000s. This feels like a piece that the Haim sisters would rock on their current era, and I would honestly lean into other style signifiers of the time. Try it with layered tank tops in different colors (and colorful exposed bra straps, while you’re at it), or a delicate pointelle long-sleeve tee (perhaps even with a slight bell sleeve?) topped off with colorful pointy-toe heels (another excuse to hit up eBay to see if you can find the perfect old Miu Mius or Manolos to go along with it).
The Vintage Sneaker
@oooyouswaggin came across these sneakers just in time, I think, as we’re in a bit of a boxing sneaker moment. And yes, I know these aren’t actually boxing sneakers, but sometimes you don’t need to do the trend exactly as other people are doing it, but rather interpret your version of it— almost in an Impressionist style, zeroing in on the general idea of the silhouette (which is a high-top that is not too ornate or puffy). The red pair feels like the one you could get the most mileage from right now, because primary colors are also having a moment (see Michael Rider’s debut collection for Celine). If you’re a skinny-jeans person (also a Rider/Celine thing), I would say go for it. If you aren’t, I would suggest you go with the narrowest width of pant leg you feel comfortable with, because the point is to really show off the sneaker, not hide it underneath a super wide leg. Another cool thing you could try would be to experiment with the color of the shoelaces. White is obviously good, but what might a tonal red look like? Or even something close-but-not, like magenta?
The Vintage Bag
Fellow Vogue-ette Sam Ravin and user @poppyharvey shared small baguette-size bags from the early aughts (the former, an incredible vintage pony Fendi, and the latter, a denim-and-leather Dior). My honest take is that both of these bags are so iconic that you should just be wearing them every single day, but that’s not what you want to hear—or is it? I could see both bags easily worn with all-denim looks. Whether you fully lean into the vibes of the era is up to you, and you can do so with a pair of low-rise flared jeans and a cropped, fitted denim jacket (worn as a top); a pair of balloon jeans and a denim shell; or a simple dress. But I could also see them holding their own against more striking contemporary looks: a slouchy tee half-tucked into wide-leg pleated wool pants; a proper tailored suit; or even something more bohemian, like a funky printed pareu worn over loose cotton pants and an off-the-shoulder open-weave top. With pieces like this, the instinct is often to “save them for a special occasion,” but every day you get dressed is a special occasion!
