Dating can be cute. Or it can feel like an unpaid job where we review résumés and wonder why grown men still wear cargo shorts in 2024. But let’s talk about this one: you meet somebody, the vibe seems good, and then boom—he shows up in square-toe shoes and bootcut jeans. Now what?

Style matters—to an extent. So if your date shows up looking like he got dressed in the dark, should that change things?

First Impressions Are Loud

Look, clothes talk. Loudly. You might not be a fashion editor, but we all make snap judgments based on what someone wears. It doesn’t mean we’re evil—it means we have eyes. Someone walking in wearing Crocs to dinner might say, “I prioritize comfort over vibes.”

But feeling meh about your date’s outfit isn’t always a dealbreaker. You can roll your eyes at someone’s shoes and still like their personality. Still laugh at their jokes. Still be into their energy. The question is: how bad is the style, and can you live with it?

Some People Want a Wedding, Others Want a Group Chat Check-In

People want different things. Some want daily texting. Others are fine catching up once a week. You’ve got folks swiping with marriage in mind while others are out here curating their weekend roster. Preferences vary—some lean toward casual settings, others like arranged dates. Then there are setups like elite dating in the UK, where things can feel more curated and more structured. They’re not alone. Some use apps tied to interests, careers, or even faith.

It doesn’t always come down to the type of date or its setting. What matters is if both people want the same thing out of it. If one’s chasing meet-the-parents and the other’s ghosting by Monday, there’s your red flag. Matching goals matters more than matching outfits.

You Can’t Force Style

Here’s the thing: you can’t really teach personal style. You can suggest. You can recommend. You might even pull a, “hey, let’s go shopping together!” But if someone doesn’t care about clothes, they’re not about to start dressing like a Pinterest board. And you shouldn’t expect them to.

So either you accept their wardrobe as part of the package or prepare for daily eye twitches. It’s not fair to try to make someone your personal makeover project. That’s not dating—that’s arts and crafts.

Do Clothes Even Matter Long-Term?

Some researchers say most men care less about fashion and more about comfort. So if your guy’s outfits make you cringe but he treats you like a queen, you may need to choose your battle.

Style can change, but character? That’s baked in. Why throw away someone good over something that launders every week?

When Clothes Are a Clue

Now, if your date’s style screams “I don’t try,” that could be a sign of deeper stuff. Like lack of effort. Or cluelessness. Or not thinking highly of the occasion. If someone pulls up to your third date in gym clothes like y’all are about to do squats together, that might be less about style and more about effort.

Pay attention. It might not be about the outfit—it might be about what the outfit says.

Final Take: Bad Shoes Are Annoying, But Not Always Fatal

You don’t have to love every piece of clothing your partner owns. You don’t need to rank their drip a 10 out of 10 every day.

But you do need to like the person inside the fit. If you’re more into tailoring than tees, that’s fine. But don’t expect everyone to be a fashion plate.

If you like the person, find the beauty in their flaws—even if those flaws come with Velcro.