There’s a reason some looks never go out of style—they’re flattering and fun, they make an impact and they call back to our favorite timeless icons. I’m talking, of course, about hallmarks such as Elizabeth Taylor’s cat eye, Frank Sinatra’s fedora, and Jackie Kennedy’s oversized shades.

Today, more than ever, style is expansive and forgiving. You can wear whatever you want—and rock a classic look to great effect when you do it right. “Life is too short not to wear what makes you happy,” says Los Angeles-based stylist Kat Eves. “That being said, most of us have spaces we have to move in where we can’t let our full vintage freak flags fly at full mast.”

Pick a Focus

Choose the “centerpiece” of your look, says Eves. “Wearing all vintage all the time leans more into cosplay territory than everyday style, and the upkeep and expense for keeping that much vintage from going threadbare can add up quickly. Choose one standout vintage piece that you truly love—the item that you always get complimented on—and build your modern look around that,” she says. She uses the example of a vintage 1960s Hermès scarf. “Paired with a 60s mod shift dress, it could read a little flight attendant (an aesthetic I love, personally), but to bring it back down to Earth today, you might pair it with a more modern and simple cotton or hemp dress, or even a plain T-shirt and ‘90s-style blazer and wide-leg pants for a mixed-decade look that is more elevated casual.”

Vintage Don’ts: When in Doubt, Leave It Out

“If there’s anything in your vintage closet that you’d have to defend with ‘it was a different time,’ it’s probably best left in the past,” Eves says. “Avoid any clothing or accessories featuring people of color in native dress or traditional garb, and definitely give up the tiki-god-print luau shirts. There are lots to love about the fantasy world of tiki bars and style, but the real-world racist implications of made-up Hawaiian gods, grass-skirt hula girls and sometimes even fake Asian writing have to be addressed and cleared out. The same goes for anything with confederate flags and slave imagery, of course.”

There’s also a fine line between paying homage to a culture and culturally appropriating. Eves says the general rule of thumb is if it’s something that holds significance in a culture other than yours—think of the uproar a traditional Chinese dress worn to the prom caused last year—you probably shouldn’t wear it.

“If it displays people of color as workers or servants, skip that, too. Exploiting people is a bad look! That doesn’t mean you can’t drink piña coladas and Mai Tais while rocking a pinup wiggle dress; it just means being mindful of culture, history, and respect for other people,” Eves says.

Making It All Work
The great thing about dressing vintage is that you have so many eras to choose from, and you can then mix and match. “If you want to be a little more daring, add a few hard edges into your look. Rock a vintage floral caftan with a studded belt. Pair a cutesy Peter Pan collar dress with combat boots. Uplevel a plain black jumpsuit with Elton John-level platforms and big 70s gold statement earrings,” she said.

For masculine looks, vintage suiting is actually an advantage for those with broad shoulders, muscular thighs, and bigger midsections—most of today’s suit designers favor a slimmer fit. “Just remember: shopping vintage doesn’t mean skipping the tailor,” Eves says. “To dial the suit in just to your body, you may need a few alterations here and there.”

Get the Look

1950s

Women: Think Rizzo from Grease and show some cleavage in curve-hugging dresses (below the knee, thank you). Go with a bold-color lip—red or pink—with a solid, dark arched brow and thick mascara and velvety matte powder.

Men: It doesn’t get any more classic than James Dean and his iconic white tee (you can skip the cigarette pack rolled up in the sleeve though). Add some jeans turned up at the ankle with a modern shoe.

1960s

Women: A bold-patterned, loose shift dress is an easy summer choice, paired with flats and a Bridgette Bardot-style loose updo. Try pale lipstick and swooping winged eyeliner.

Men: Go for slim-ankle pants with Beatle boots, which have never really gone out of style (but do eschew the Beatle mop-top haircut). And maybe this is your moment for the sweater vest?

1970s

Women: All hail the graphic-print maxidress, which is comfortable, forgiving and universally flattering. For hair, let your natural curls go wild or part straight hair down the middle.

Men: A wide-lapel leather jacket gives you instant badass cred (hey, Mod Squad!), and you can pair it with pretty much any pair of pants except the dreaded Dockers style.

1980s

Women: Yes! You can cut out the necks of all your slouchy sweatshirts, which you can wear over leggings and boots and call it a day. Add a neon-hued accessory or stacked bangles for instant insouciance.

Men: Say yes to vintage Nikes, which have made a comeback, and perhaps a pink linen jacket à la Don Johnson for summer. It’s just what the fashion doctor ordered.

Got your favorite pieces lined up? Most style philosophies fall into two categories, Eves says: Iris Apfel’s “more is more” and Coco Chanel’s “take one thing off.”

“If you wear a full outfit of shiny things, two things happen: the eye doesn’t know where to focus, and the actual person under all that glitz gets lost,” Eves says. “If you’re wearing sequins on your 1950s cardigan, skip the rhinestone necklace (and the matching earrings). Dress it down with jeans and a lacy tank, and now you have a very cute, cool girl look that’s great for a Tinder date without trying too hard.”