How to Wear Vintage Today: Classic vs. Recent

Mix it up with today’s accessories. The look to aim for is imperfect, raffish, even deliberately artless.

By Linda Dyett

Ladies who do vintage: Linda Rodin, Tziporah Salamon, Iris Apfel. Photos by Ari Seth Cohen at AdvancedStyle.blogspot.com.
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Classic Vintage starts a century ago with the high-waisted tunics and hobble skirts of World War I, followed by ’20s Flapper styles. These look decidedly costumey today (as per Downton Abbey and Boardwalk Empire). More wearable are the sinuous bias cuts of the ’30s, the austere masculine-feminine ’40s styles, and the Mod ’50s and early ’60s, replete with fit-and-flare shirtwaists and slinky cocktail dresses. All these decades offer assured feminine styles, virtuoso workmanship, lush fabrics, and an elegance too often missing from more recent fashion. Customers tend to be devotees of all ages, but they skew midlife and older, according to most dealers. “These are women with confidence in their style, says Jennifer McCulloch, owner of Olive’s Very Vintage (no longer open) in Brooklyn. But beware: Classic Vintage is cut small, though large sizes can be found.

If you go that route, don’t make the mistake of accessorizing with shoes or accessories from the same period. If you do, you’ll risk looking like you’re caught in a time warp or are on your way to a costume party.

What’s essential with Classic Vintage is updating its context: Make it less formal; undo its decorousness, wear it knowingly, raffishly, even ironically, by mixing it with contemporary. The intention, says Pam Coghlan, owner of the pre-’60s Odds & Ads, is “looking imperfect and artsy. That’s what makes it modern.”

So wear a ’40s rayon dress with, for instance, textured tights, Swedish sandal-clogs, and maybe avant garde or tribal jewelry. Top a ’50s shirtwaist with a jeans jacket. And rather than dismiss a ’60s or ’90s mini-chemise as too short, wear it over a billowy skirt or chinos. The contrasting retro-ness of vintage makes it contemporary. As for hair style, keep it casual (not coiffed), and makeup minimal.

Swedish Hasbeens boot clogs; Thriftwares ’90s chemise, & new slip dress; ’30s-’40s hat & dress, Dividing Vintage Moments blog.
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Recent Vintage covers the hippie years, disco ’70s, power dressing ’80s, and the spare and minimal ’90s. Excepting a scattering of big-name couturiers, mid-level designers (the likes of Rudi Gernreich, Norma Kamali, and Helmut Lang), outliers like the avant garde Japanese and Belgians, and a few inspired no-name boutique designers, I view the styles of these decades as cartoonish re-hashes of Classic Vintage that haven’t evolved much in the new century. Remove the ’80s shoulder pads, adjust the hem lengths, and recent vintage is all but indistinguishable from contemporary fashion. Intricate workmanship and subtle nuances, out. Roomier cuts and forgiving fit, in. Not a happy trade-off. But the easier fit means that many Boomers and older women continue wearing the ’80s and ’90s—which have never stopped being current for them. For entirely different reasons, Recent Vintage is also favored by Millennials, who crave the more extreme dynasty dresses and grunge-wear their mothers wore. Barbara Kennedy, a dyed-in-the-wool dealer of Classic Vintage, describes these young shoppers as “early collectors, figuring out what they want to be when they grow up. They should just go to Goodwill and be done with it.” Ouch!

Ensembles that mix vintage and modern, from Jessica Quirk’s What I Wore blog (no longer online).
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Linda Dyett’s articles on fashion, beauty, health, home design, and architecture have appeared in The New York Times, Washington Post, Monocle, Afar, New York magazine, Allure, Travel & Leisure, and many other publications.

Updated Feb. 8, 2022