Yes, Sophisticated Going-Out Tops Exist—And They Look Nothing Like What You Wore in the 2000s

At the time, of course, we thought the going-out tops of our youth were the be-all-and-end-all of fun evening attire, but hindsight has a way of putting trend-driven missteps in perspective. Thankfully, none of the myriad upgraded options hiding in recent designer collections look as though they were copped from Mischa Barton’s “The O.C.” dressing room.

Skeptical? Observe the quietly sensual Saint Laurent style Zoë Kravitz teamed with leggings to attend the brand’s February fashion show in Paris (center of the collage, above); the sheer Alaïa bodysuit Rihanna recently wore; or even the shoulder-pad-bolstered black T-shirt from Isabel Marant’s spring collection.

The ostentatious tops of the aughts had a sort of built-in obsolescence. “When you’re younger, you’re like, ‘Oh, this will be so good for this [party]’ and then you never think about it again,” said New York City stylist Danielle Goldberg. “As an adult, it’s about investing in pieces that you’re going to wear weekend after weekend in different ways.” Her pick of this season’s offerings is Khaite’s off-the-shoulder Cerise bodysuit in stretch cotton, which would look equally chic at dinner with jeans beneath a blazer or on the dance floor atop a leather mini skirt.

Speaking of dancing, how many of us are abandoning our spreadsheets and/or children and/or commitment to reading “Succession” recaps to jump on the bar and break it down like the stars of the 2000 flick “Coyote Ugly”? The nighttime plans of many former going-out top devotees have evolved along with their wardrobes. Some have to march straight to cocktails from work.

Rakia Reynolds, founder of Skai Blue Media, a public relations agency with offices in New York, Philadelphia and Los Angeles, said she’s “recalibrated” her going-out top approach since becoming her own boss in her 40s. “In my 30s, it was jeans and a cute shirt—anything that showed my collarbone and arms,” she said, citing spaghetti-strap tanks and bustiers as go-tos. These days, her shirts must do double duty as professional wear. “I love a top I can wear to all my meetings and then spruce up with accessories to go out after a busy workday,” she said. “Anything with a collar [is great] because I can wear it buttoned-up with jewelry or unbutton the top button and completely change the look.”

Another thing few of us heeded while sowing our wild oats? Comfort. Before becoming one’s fully formed self, one often cares more about earning validation in torso-torturing fashion than, say, getting to wear cloud-soft jersey all night. “Ultimately, it’s about leaning into whatever you feel best in, not necessarily what the trend is at the time,” said Ms. Goldberg. If you feel best in a T-shirt, that’s A-OK, she said, suggesting a silk one from the Row.

Sarah Staudinger, 34, founder of fashion label Staud and frequent going-out top wearer, says she and her studio are working on designing the “perfect sexy T-shirt” in a lightweight cotton and a comfy knit for next summer’s collection. The strategy: It discreetly hits below the waist, but elegantly reveals your decolletage, which she calls “the most flattering part of a woman’s body.”

At the Dallas boutique FortyFiveTen, fashion director Jordan Jones Muñoz has noticed women gravitating toward ultrafeminine options from such brands as Magda Butrym, Erdem and Cecilie Bahnsen. Airier styles with what she called “cool-girl volume” have also proven popular.

However, at the end of the day, a going-out top is whatever you want it to be, said Ms. Muñoz. “If it makes you feel a little more dressed up and special, it’s a going-out top.”

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Five chic women remember their Y2K party tops

“My most-loved top from the 2000s is a custom blue-and-white cropped baseball shirt. It’s the epitome of fashion at the time. I refuse to give it away.”—Christina Milian, 41, actress, Los Angeles

“We dressed like that because we didn’t know any better. We didn’t have access to every fashion reference on our phone like kids today. If I had, would I have worn a backless silver lamé cowl-neck halter top? Maybe.”—Lauren Santo Domingo, 47, co-founder of Moda Operandi, New York City

“I’d prefer to forget most Y2K fashion, but I loved tube tops. I used to go to Tube Top Tuesday at the University of Wisconsin. I had them in almost every color.”—Katie Sturino, 41, Founder of Megababe, New York City

“I still have all of my going-out tops. I have every sequin top, every vintage Saint Laurent and McQueen top. I don’t get rid of my favorite things. I would style them similarly to how I did back in the 2000s, with a pair of jeans and tall platform heels.”—Rachel Zoe, 51, co-CEO of Rachel Zoe Inc., Los Angeles

“My favorite was an antique fringed silk paisley scarf I found at a flea market. I wore it as a strapless top by folding it into a triangle and tying it in the back. It made me feel like Gisele.”—Rachael Wang, 38, stylist, Ojai, Calif.

—Edited from interviews by Jessica Gibbs

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