First impressions aren’t just about what you say–they’re about what you wear, too. And when it comes to dating, the wrong outfit can say a lot more than you realize. You could be smart, kind, and funny, but show up in a sloppy or mismatched look, and it might read as lazy, immature, or out of sync with the occasion. You don’t need designer labels or a full makeover–but you do need to look like you care. The trick is dressing with intention.
Here are 20 things you should never wear on a date–especially if you want a second one.
1. Overly graphic T-shirts
A shirt screaming a slogan or plastered with a giant cartoon doesn’t show personality–it shows a lack of effort. On a date, your words should do the talking, not your shirt. Keep it clean, solid, or subtly patterned. Graphic tees may be fine for lounging with friends, but they’re rarely a good look for someone trying to make a romantic impression.
2. Wrinkled anything
Nothing says “I don’t care” like stepping out in a crumpled shirt or pants that look like they’ve been living on the floor. It doesn’t matter how expensive your clothes are–if they’re wrinkled, they look cheap. Iron your clothes or invest in a steamer. It shows you take pride in your appearance–and by extension, that you’ll take pride in the date, too.
3. Excessive cologne
Yes, smelling good matters–but smelling too good is a one-way ticket to headache city. If your scent enters the room before you do, it’s too much. A few subtle spritzes on pulse points is all you need. The goal is to be intriguing, not overpowering. Let her lean in, not lean away.
4. Flip-flops
Unless you’re literally on a beach, leave the flip-flops at home. They signal zero effort and, frankly, don’t flatter anyone’s feet. Footwear is one of the first things people notice on a date. Opt for clean
5. Pants that don’t fit
Too baggy and you look like you borrowed them. Too tight and you look like you’re trying way too hard. Proper fit is everything. A tailored silhouette instantly elevates your appearance and boosts your confidence. Take the time to get pants that actually flatter your shape–and if needed, visit a tailor. It’s worth it.
6. Dirty or scuffed shoes
Shoes are quiet confidence signals. You don’t need brand-new kicks, but you do need clean ones. Dirty
7. Sunglasses indoors
Wearing sunglasses inside makes you look like you’re hiding something–or worse, trying to act like a celebrity in disguise. It’s a date, not a music video. Eye contact is key to building connection, and sunglasses block that. Take them off and show you’re present and engaged.
8. Sports jerseys
Unless you’re headed to a game together, leave the team colors at home. Jerseys can make you look like you haven’t mentally left your college dorm. Save them for game night with the boys. On a date, you want to show your grown-up style–something with a little more intention and maturity.
9. Clothes with visible stains
No one’s perfect, but stained clothing gives the impression you just grabbed something off the floor and hoped for the best. Even a small stain can pull focus and break the spell. Always check your outfit in good lighting before heading out. If it’s got a stain, it’s not a date outfit.
10. Overly formal suits
Showing up to a casual dinner dressed like you’re heading to a board meeting creates awkwardness. Overdressing can make your date feel underdressed–and uncomfortable. Always match the vibe of the venue. Smart casual usually strikes the right balance: sharp, but not stiff.
11. Offensive or polarizing slogans
T-shirts with edgy jokes, political statements, or crude humor can derail a date before it even starts. You might think it’s funny or clever, but it could come off as aggressive or immature. Save the opinions for the conversation–not your clothes.
12. Baggy cargo shorts
They’re practical, sure–but not flattering. Unless you’re hiking or running errands, cargo shorts make it look like you didn’t even try. Swap them out for tailored chino shorts or slim-fit jeans if it’s a warm day. A small upgrade can completely change how put-together you look.
13. Too much jewelry
Accessories can enhance your style–but overdoing it screams insecurity or flashiness. Rings on every finger, thick chains, and wrist stacks can distract from you. Keep it simple: a clean watch, a single chain, or a tasteful ring is more than enough. Heavy jewelry have their place; a first date may not be it.
14. Loud patterns
You want to be remembered for who you are, not because your shirt gave someone a migraine. Neon paisley or busy graphics can overwhelm the visual space. Stick to classic patterns–stripes, subtle checks, or solid colors–and let your personality take the spotlight.
15. Oversized hoodies
Comfort’s great, but a giant hoodie makes it look like you’re hiding or still mentally in your teens. It can make your body look shapeless and your vibe uninterested. Opt for a fitted sweatshirt, cardigan, or jacket instead–something that says you care about comfort and style.
16. Visible undershirts
If your undershirt is peeking out from your collar or sleeves, it looks lazy. The purpose of an undershirt is to stay invisible and provide structure or sweat protection–not to be part of your outfit. If it shows, swap your layers or go without it altogether.
17. Hats indoors
Unless it’s part of your religious or cultural identity, take the hat off once you’re inside. A baseball cap at the table makes you look like you just wandered in from an errand. It blocks eye contact, casts shadows on your face, and gives off a casual sloppiness that doesn’t belong on a date.
18. Deep V-neck shirts
Trying too hard is just as bad as not trying at all. A plunging V-neck often comes off as a thirst trap rather than a style statement. Stick to classic crew or modest V-necks–they’re universally flattering, effortless, and don’t scream for attention.
19. Too many visible logos
Wearing a billboard of designer labels doesn’t make you look rich–it makes you look insecure. Subtlety is class. One small logo? Fine. But if your entire outfit reads like a sponsorship deal, you’re doing too much. Let your presence–not your labels–speak volumes.
20. Pajama-like loungewear
Casual doesn’t mean careless. Loungewear might feel good, but it rarely looks sharp. Joggers, oversized tees, or fuzzy fleece scream Netflix, not connection. On a date, show that you’ve transitioned out of home mode and into “I’m here for this” mode. It shows respect–for the occasion, and for them.
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