What It’s Like To Be An Overdressed Girlfriend-Underdressed Boyfriend Couple

As the internet has long noted, Hailey and Justin Bieber often look like they’re dressed for two completely different events.

That was never more apparent than late last month, when the Biebers stepped out for lunch and a work event at Krispy Kreme in Manhattan for Hailey’s makeup line, Rhode.

While Hailey showed up in a snatched red mini dress with matching accessories and full glam, the Biebs kept it very “I’m going to a donut shop” in a sweatshirt, a pink baseball cap and his finest Crocs.

“He’s always dressed like he’s about to go help his mom bring in groceries from the car,” said one astute critic on X, the social media platform formerly known as Twitter.

Some were a little put off: “I would’ve left him in the car,” one person said.

“If your partner dresses up to go to Krispy Kreme you should dress up too,” wrote menswear writer Derek Guy.

The Biebers, it seems, are the highest profile example of the overdressed girlfriend/underdressed boyfriend meme: TikTok is full of couples showing off their clashing ensembles, usually with the husband or boyfriend slacking it in shorts, a T-shirt and a hat. (And if you’ve ever been to a nightclub, you’ve no doubt encountered dress-code flouting, underdressed men partnered with dressed-up women in the wild.)

Other notable celebrity examples of this dynamic through the years? J.Lo and Ben Affleck and on occasion, Kim Kardashian and her now ex Ye, formerly Kanye West.

Mayumi Handa, a 26-year-old who lives in the Salt Lake Valley area of Utah, says the “overdressed girlfriend/underdressed boyfriend” dynamic has been present in pretty much every relationship she’s ever been in, including her marriage.

“I am very extra with my outfits, hair and makeup and try to always look good regardless of where we’re going,” she told HuffPost.

Her husband, meanwhile, lives in sweat shorts and Carhartt T-shirts, even when they’re going to dinner.

“We went to a bar a little bit ago with some friends and that’s exactly what he wore and I wore a full-on clubbing outfit,” Handa said. “He’s definitely a ‘I want to be comfortable’ kind of guy and I’m more like, ‘I want the drunk girls at the bar to compliment my outfit’ kind of girl.”

As soon as she saw the pic of the Biebers, Handa could relate: “I will say, I think that might’ve been a situation where my husband would’ve had to step it up and at least wear pants and sneakers,” she said. “But I do think the trend is funny in general.”

Influencer Cina Lukas is also perfectly fine with her husband dressing for comfort over style. Then again, marrying a Hawaiian, she didn’t have much of a choice.

“It’s super casual, shorts and T-shirts almost every day for him, and he always wears slippers ― people in Hawaii always wear slippers,” she told HuffPost. “No matter where we go ― fancy dinners, even weddings ― he wears shorts and slippers.”

Lukas’ husband even has a pair of shorts that work as board shorts and formal shorts so he can go straight from the beach to dinner or a bar.

“My feeling is, he can wear whatever he feels comfortable in,” she said. “But of course you gotta read the room ― or the invitation ― and at least dress up a little bit to match your partner if it’s a more formal or special event.”

Tom Powell, a 23-year-old Cambridge student and TikTok creator, is one half of an overdressed boyfriend/underdressed boyfriend coupling, too. His boyfriend, Christian, is the Bieber in the relationship.

“Usually if me and my boyfriend are attending something important, I’ll make sure we coordinate over text beforehand. It looks like Justin didn’t get the memo,” Powell joked.

Generally, Christian dresses down as much as possible: “I remember one time there was a black tie event at my college, and he turned up in a T-shirt,” Powell said. “I don’t usually mind, though; it makes me look classier by comparison!”

Not all better-dressed halves are so forgiving, though.

Shany Monroy Skoog, a 23-year-old influencer from Los Angeles, almost ruled out dating her husband because of his lack of style.

“I’m not going to lie, I did not like the fact that he would wear Birkenstocks or sandals with khaki shorts, a graphic superhero shirt and a hat. It just wasn’t my thing,” Monroy Skoog said of her schoolteacher husband.

Eventually, she caved. (Plus, he dresses up when it’s really matters: “When we went to go see ‘Barbie,’ he wore pink and he dressed up as Ken for me because he really knew that I was excited for this movie.”)

“I learned to love him for who he is and how he treats people and his priorities,” she said. “And he knew me already as a content creator: someone who loved dressing crazy and doing my makeup crazy and stuff like that. He liked that about me.

Jasmyn, a 34-year-old from South Dallas, never really learned to love the “raggedy” way her ex-husband dressed when she was dressed up. If it wasn’t a funeral or a wedding, he was in a graphic tee and old jeans. Though she never complained, it created some awkwardness for the pair.

“After about five or six years of marriage, he finally mentioned that people looked at us weird, and he felt sloppy next to me,” said Jasmyn, who asked to use her first name only for privacy.

While she certainly didn’t expect her ex, who’s a Marine, to spend an hour in front of the mirror getting ready like she did, she did wish he’d put some thought into fit: “He is 5’7” and insisted he needed a 30-inch inseam, so you can imagine the bottoms of his jeans,” Jasmyn said.

It wasn’t until after the divorce, when she started dating someone who dressed up, that she realized how much she valued a little sartorial effort.

“The last person I dated was truly the most beautiful human I’ve ever seen. They didn’t wear traditionally masculine clothes ― they are AMAB non-binary ― but they had personal style,” she said. “Nothing over the top, but clearly coordinated, and they could even manage to make tank tops look stylish.”

Given her past experience, Jasmyn wasn’t a fan of Bieber’s cozy, Crocs-centric look.

“That’s for an event? He’s dressed like that to do something other than laundry? And he has the money to not look unwashed?” she said. “I hope she leaves him over the blatant disrespect.”

Stephanie Santos, a 28-year-old fiction writer, has also dated her fair share of underdressed men. Her current boyfriend is a little different.

“He’ll still wear basketball shorts if we’re running errands, but if he sees I’ve put in a little more effort just to run to the grocery store, he’ll say something like, ‘Oh no, I look like a scrub next to you!’” she said. “I think it’s sweet that he wants us to look cohesive next to each other.”

With Bieber, she gets it; part of the “Yummy” singer’s brand is dressing like an elevated scrub (“elevated” because his sweats are no doubt exorbitantly priced). But in general, she encourages men to step up their fashion game, if only because it can be genuinely fun to experiment.

“I don’t say that because I think they should have the same pressures women have to look a certain way, but because it’s fun,” she said. “My style, and subsequently my personality, really changed when I stopped caring what people thought about the way I looked and started incorporating fun colors or textures into my wardrobe.”

She pointed to fashion-forward men in the 1970s who dressed flamboyantly, and sometimes even showed up their girlfriends: Steve McQueen, Marvin Gaye, Mick Jagger.

“None of them did it the same way ―they were expressing themselves,” she said. “I think men dress down because they’re scared people will think they look ‘weird’ if they did fashion ‘wrong,’ but truthfully, even if the outfit isn’t perfect, you can tell when a guy puts thought into his outfit and is feeling himself.”