Better in their words…

After a year when serious concerns took precedence, there’s no shame in being blissfully stuck in a bygone era. But as we emerge from our Zoom cocoons, the time is ripe for reassessing our fashion choices and stepping up our wardrobes for a post-pandemic era—within reason, of course. “Seven-inch stilettos don’t line up with what we’re going through right now,” said New York fashion-brand consultant Dani Stahl. And don’t let beautiful celebrities be your sole style guides—they can make almost anything look fabulous. “What looks dated on one person is supercool on another,” she said. “If [model] Bella Hadid puts on tight jeans, it’s current, but elsewhere can look off.” That means they’ll be “off” on me, I think, and many, many others.

What makes an outfit outdated? Recognizable fads—like message-print T-shirts or early aughts-era no-show socks—are outfit poison, and fallbacks like chinos and shapeless cardigans are cringeworthy relics. A garment’s cut, too, can read “outmoded.” “You don’t want to look like you’re in a jacket from 30 years ago, so updated fits come into play,” said Paul Stuart creative director Ralph Auriemma. He suggested tailored sportswear for a sleeker, modern fit.

As we plan our re-entry outfits, comfort remains a factor, said Tracy Margolies, Saks Fifth Avenue’s chief merchant, “but people want to be stylish.” That’s why stifling skinny jeans, for instance, bow to straight-leg options and roomy denim joggers. Below, 10 men’s and women’s styles that will subtly date you—and advice on how to bring your wardrobe back to life.

Demurely Bucolic Dresses

Why They’re Out: In my college years, I called dresses from the commercially quaint British brand Laura Ashley “Heidis,” named for the classic children’s book by Johanna Spyri about an orphan growing up in the Swiss Alps. Today’s frilly, floral dresses—described by many as “cottagecore”—nod to Laura Ashley’s 1980s Liberty-print frocks and conjure a campy frivolity at odds with our 2021 selves. “Cottagecore sounds like a house muumuu…it’s very dated,” said Ms. Stahl, the fashion-brand consultant.

Upgrade: If you can’t quit botanical prints, try Merlette’s equally flowy but less saccharine shibori-dyed floral dress. Dress, $460, merlettenyc.com

Almost-Invisible Socks

Why They’re Out: Pioneered by 1960s French mods known as the Bande du Drugstore and codified in the tongue-in-cheek 1980 manual “The Official Preppy Handbook,” the no-socks-with-loafers look became a less stinky one in the 2000s when new-age prepsters and sneaker-loving city kids adopted low-rise socks to keep their ankles exposed and their soles sweat-free. No-shows’ popularity was good news for America’s declining sock industry, but today they say, “I’m an out-of-touch millennial clinging to a trend my dad ditched years ago.”

Update: Instead of no-show socks peeking out from your sneaker, try an over-the-ankle pair in a punchy color that makes it clear these socks are meant to be seen. Socks, $15, theentireworld.com

Screaming T-shirts

Why They’re Out: In the 1970s, Malcolm McLaren and Vivienne Westwood decried the state of the British monarchy with ironic “God Save the Queen”-print T-shirts from their Seditionaries label. Fast forward to 2016 and Dior’s $710 “We Should All Be Feminists” tee, quoting writer Chimamanda Ngozi Adichie, became ubiquitous Instagram fodder. Right now, there are many messages worthy of our attention, from “Say Her Name” to “Black Lives Matter.” But if your signature style is a cotton top emblazoned with some 2020 cliché like an empty cry for “empathy” or the thoroughly unfunny Zoom joke “Can everyone mute please?”, it’s time to pipe down.

Update: Let your T-shirt’s design do the talking, like the soothing, painterly picture on this souvenir style-tee. T-Shirt, about $140, casablancaparis.com 

Suffocatingly Slender Denim

Why They’re Out: Elvis wore them in the 1950s. The Sex Pistols flaunted them in the ’70s. In 2006, British supermodel Kate Moss made them trendy yet again. But squeezing into skinny jeans today—particularly if you pair them with a blazer and pointy stilettos, or a too-tight plaid flannel and an equally pointy pair of chelsea boots—will place you in a bygone decade. Or worse, it could get you fashion-cancelled on TikTok, where Gen Z has boisterously condemned skintight denim.

Update: Make the transition away from skinny denim easy and try a go-with-everything straight-leg pair. Jeans, $248, Frame, 323-879-6116

Sad, Shapeless Sweaters

Why They’re Out: The woefully generic “mom cardigan” is button-free and hangs long in the back. Designer Eileen Fisher helped popularize the oversize knit in the 1980s, and her company continues to churn out roomy versions. While the mom cardigan is somewhat blobbish, its simplicity and raison d’être (to cover a widening behind) contribute to its enduring presence in both luxury and fast-fashion collections. But wearing one—especially over leggings—will seriously date you, indicating that you’ve reached a “too lazy to try” age that’s not an era but a state of mind.

Update: Your outer layer should have a closing mechanism as a rule—think buttons or belt. This cardigan coat with a detailed trim and an intentional closure avoids the mumsy look without losing any of that covatable coverage. Sweater, about $350, ven-store.com

Sustainable Slip-Ons

Why They’re Out: Made from recycled plastic bottles, San Francisco brand Rothy’s line of knitted, eco-minded flats for women and kids emerged in 2016 as consumer awareness about fashion’s impact on the environment was growing. Conscious sneaker label Allbirds does a guys’ version—they’re crafted with eucalyptus trees and would probably say “namaste” if they could talk. Facebook groups helped fuel the popularity of these slip-ons, and fans bought, traded and gushed about the comfy cuteness of their pairs online. These flats are the Beanie Babies of shoes and date you as someone who still uses Facebook as your primary social-media platform.

Upgrade: If eco-friendly flats make you feel good, try this sleek vegan-leather pair from Aera, a sustainably minded small business that’s big on style. Shoes, $450, aeranewyork.com

Bohemian Purse Straps

Why They’re Out: In early 2019, the woven, graphic Salt strap became a badge of bohemian chic in Brooklyn. Handwoven in Colombia from natural materials, Salt straps, which start at around $130, seemed a practical, supercool way to update your go-to cross-body bag. Plus, the interchangeable straps kind of curbed the snootiness of pricey designer bags, making them appear craftsy instead of fancy. Now, however, when preciousness seems pretentious, swapping straps on $5,000 purses just sends out “Privileged Park Slope Momster” vibes.

Upgrade: If you love the durability (and statement pattern) of a removable strap, try a fanny-style cross-body. The thick nylon strap is just as tough and the floral just as fun. Bag, $195, loefflerrandall.com

Fratty Florid Dress Shirts

Why They’re Out: For the longest time, super-bold printed shirts have been popular with men who like hitting the town. The unrelenting trend possibly devolved from the flamboyant 1960s fashions of London’s Carnaby Street mods. Today, myriad brands including Ted Baker London and Robert Graham offer shirts with unpleasantly punchy patterns, which are sold at stores like Nordstrom and Neiman Marcus. But “the thing is, I never see stylish guys wearing them, so I don’t know who buys them,” said Mr. Auriemma, the Paul Stuart creative director. He might need to visit a seedy nightclub to find the answer.

Update: Paul Stuart creative director Ralph Auriemma suggests you opt for a shirt with a dress collar and an “elegant” print. In other words, keep it classic with just a splash of color—and leave the neons at the mall. Phineas Cole Shirt, $485, paulstuart.com

Over-the-Top Earrings

Why They’re Out: A bit desperate for some display of fashion, many women reached for chandelier earrings last year, hauling out lookalike versions of Queen Elizabeth’s 1929 Cartier Greville jewels to watch “The Crown” with friends over video chat, or sporting a flashy crystal pair to bring some oomph to work meetings. But now, chandelier earrings indicate you’re stuck in a 2020 Zoom loop. 

Update: To change things up, opt for a big beaded collar like this one—perfect for Zoom and festive enough for our return to dinner dates. Plus, it will indicate you’ve moved on from your Royals-centric streaming obsession to a more “now” series like, say, “Call My Agent.” Necklace, $525, sophiebuhai.com

Drab Beige Pants

Why They’re Out: In a word, squaresville. Ms. Stahl warned that only the very young or very gorgeous could make “Dad chinos” look fresh. The dorkiness of this army classic, which gained popularity during the 1898 Spanish-American War, was cemented in a “Seinfeld” episode in which Jerry dates a woman named Donna, who likes a Dockers commercial he hates for its glib guys and quick shots of dowdy “pants, pants, pants!” The episode aired in 1991—a sure sign the unfashionable favorite will date you.

Update: A looser-leg cargo trouser—like this pair in laid-back green—is the new no-fuss staple, and an excellent alternative to conservative chinos. The stylish details like cinchable hems and a flat-front waistline are especially fashionable. Beams Plus Cargo Trousers, $320, mrporter.com

Corrections & Amplifications
An earlier version of this article misidentified the dinosaur in the illustration as a T-Rex. It is a Velociraptor. (Corrected on April 10, 2021)