Lifestyle Dating Tips

Every Guy I Date Dresses Worse Than the Last—and TBH, It Feels Disrespectful

Allie Flinn

January 11, 2019

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I once went on a date with a guy who showed up wearing jeans and a T-shirt. Totally normal outfit, except the tee was actually just functional workout gear being taken on a fun night out, and the slip-on Vans rounding out his #lewk were threadbare at best. I, on the other hand, wore a dress, cute sneakers, and a leather jacket that felt casual but totally appropriate for the trendy bar and potential new fling. The way I saw it, if he were really interested in pursuing something with me, he was not—as they say—dressing for the job he wanted. But I've been on enough dates to know that his attire was hardly an anomaly: So many people—at least the hetero, male-identifying ones who I have the pleasure of meeting for at least a few poorly dressed minutes—are awful at dressing for dates, making their female companion look like they're headed to a couture fashion show by comparison.

It's nothing new, either—that scene in Clueless, where Cher laments men's fashion choices, totally still rings true: "It looks like they just fell out of bed and put on some baggy pants and take their greasy hair—ew—and cover it up with a backwards cap and we’re supposed to swoon?" she says. "I don’t think so!"

I get the allure of doing the bare minimum—to some extent, at least. We're all playing that awkward dance of wanting to look good, but not like we tried to look good. But seriously, ghosts of bad dates past: When you wore your sunglasses on the back of your neck while we were inside, you basically killed any sort of sexual desire I might have had for you. Imagine saying, "Yeah I knew he was the one when I saw him wearing cargo shorts and a puka-shell necklace." Are you LOLing to yourself about it? Same. So, why is this a thing, and why is this the norm? I mean, Ed Sheeran can't bother himself to put on a freaking button-down while crooning next to a gown-clad Beyoncé? That's not BDE—that's just plain rude.

Since I've been on many an outfit-mismatched date but am no closer to decoding the root cause, I turned to celebrity dating and relationship coach Laurel House. Her take? It's not that men don't put in any effort. Rather, they just don't know what they're doing.

"Some guys are truly simply clueless. They don’t realize that their stretched-out shirt and sneakers aren’t attractive." —Laurel House, relationship expert

"Some guys are truly simply clueless. They don’t realize that their stretched-out shirt and sneakers aren’t attractive," she says, adding that on some level, they likely do believe the outfit is becoming, and assume that you will as well. In fact, many of House's male clients indeed stress about what to wear, frantically sending her photos of possible outfits.

The solution for many of these suitors? Opting for something super comfortable—because maybe through osmosis, the sartorial choices will have nerve-calming effects. "Some guys don’t want to appear to be putting too much effort into it in an attempt to not appear desperate or too excited," she adds. "They feel like their low-key look might make a date feel the need to chase him."

Also, some guys just DGAF. They think, "this is just another of many dates, and they are expecting the normal result—a failed date," House says. "They are sick of putting in the effort when they 'know' the outcome." Well cool, real cool…. With that attitude, there's especially never been a better—or more vital—time for normalized body hair and Big Bush Energy to be a thing.

But we're not just talking about first dates, here—so that destined-for-failure excuse doesn't even land, guys. When this is the case, and the guy with the backward sunglasses makes it to multiple dates (guilty), it's okay to mention to him that he's dressing too casually, House says.

Just channel your inner Tan France, and be nice when you offer simple self-improvement tips—like that Fab 5-worthy French tuck. After all, even your suitor is wearing flip-flops as a grown adult when there's no beach or locker-room shower in sight, he's still a human being with feelings and likely good intentions. (Still not sure what Ed Sheeran's excuse is though.)

Date going terribly? Here's a list of ways to excuse yourself from the situation. And also, does it actually matter if your zodiac signs aren't compatible? (Spoiler: kind of.)