10 Things Men Shouldn’t Wear on a First Date
First dates can be stressful.
You’re trying to figure out where to go, what to do, and how not to sound boring.
And choosing what to wear adds its own stress because you know people will notice your outfit before noticing your personality.
You don’t have to show up in a suit, but at least wear something neat and appropriate.
A sloppy outfit is an instant turn-off.
So what shouldn’t you wear on a first date?
I’ve rounded up 10 things to avoid.
They’re not things like stained t-shirts or jeans with a hole at the crotch.
I believe most people know not to wear dirty or damaged clothes on a date.
So, let’s take a look at what they are.
10 Things Men Shouldn’t Wear On A First Date
Before we get into the list, I want to make one thing clear: I’m not against anything here. I actually love some of these pieces and wear them all the time. They’re just not the best choices for a first date.
1. Flip-flops and Open-Toed Sandals
Flip-flops aren’t just for beaches and pools anymore. They even showed up at Paris Fashion Week this summer.
Yes, they’re basically a summer uniform now, but don’t wear them on a first date.
Why?
First, they make you look unserious.
Even though the fashion world is starting to accept flip-flops, they’re still tied to casual settings.
You don’t see them in offices or at weddings (unless it’s the dress code).
A first date is not as serious as a business setting, yes, but it’s also not as casual as hanging around your apartment with friends, either.
Second, they can be a little gross.
This is a personal pet peeve, but I don’t love seeing people’s toes at a café or restaurant. It instantly kills my appetite.
And everything above applies to open-toed sandals, too.
So what should you wear instead?
You don’t need to show up in Oxfords, but at least go for something that covers your toes.
And if you have to wear sandals, go with closed-toe ones, such as fisherman sandals.
Skip the flip-flops.
2. Baseball Caps
This might feel a bit unexpected because most guys wear baseball caps all the time, me included.
Still, I don’t recommend them on a first date.
Here’s why.
First, they hide a big part of your face, which makes it tough for your date to really see you.
Second, caps can give off a closed-off vibe, as if you’re guarded and not fully comfortable being seen, which can be read as lacking confidence.
So, what should you do?
Let them see your face without anything blocking it. Basically, don’t wear anything on your head. Just show up with your hair looking clean and put-together.
If you really need to wear something, go for brimless options like Docker caps.
But no matter what, let them actually see you. That’s the point.
3. Skinny jeans
I read a piece in The Guardian titled ‘Skinny jeans are showing signs of a comeback. Please make it all stop.’
Dave Schilling (the author) said he hates jeans in general. Said if he had to choose between wearing denim and one of those barrels cartoon hobos wear, he’d choose the barrel.
I don’t agree with that. I love jeans.
But as for the comeback of skinny jeans? I’m with him — please make it all stop.
I get the hype around skinny jeans.
They show off your shape and look especially sharp if your legs are lean and your backside is well-fitted.
But the discomfort is real, for you and for the people watching you adjust them all day.
I’ve worn skinny jeans and kept adjusting the crotch area all day because everything was too tight down there. You don’t want to do that on a first date, in front of almost a stranger, right?
Also, a first date can already feel stressful and tense, and if you show up in jeans so tight they look like they’re about to burst, it just makes it worse.
What should you wear instead?
Chinos and relaxed-fit dress pants are always the best options.
If you’re set on denim, go for straight-leg jeans (not wide-leg).
4. Flashy Belts
Belts have come a long way — they’re not just for holding your pants up anymore.
They can say something about who you are, where you’re from, and what your style preferences are.
Some people like wearing Western belts — not necessarily because they have Western roots, but simply because they like those big, bold buckles.
Others prefer designer belts with huge logo buckles to show their taste or even as part of their identity.
Whichever type you are, just don’t wear them on a first date.
Those big, flashy buckles are generally not a good choice for a first date because they can look like you’re trying to draw attention to the front of your pants, and that’s never a good look.
Also, it can look a bit tacky and showy.
On a first date, your belt should be the most subtle accessory.
Go for a sleek, classic leather or suede belt. They’re versatile, refined, and safer for a first date.
5. Athletic & Lounge Shorts
Athletic and lounge shorts are so comfy, but keep them for the gym or lounging on your couch.
Why?
Because they look like you came straight from the gym or rushed out the door and forgot to change.
And it can send the message that you don’t care about first impressions or that you’re not serious about the date.
Or even worse, you’re immature — a man’s worst nightmare.
You might just want to be casual and easy-going, but it can be taken the wrong way.
What should you wear instead?
Pants or trousers, whatever you call them, should always be the first choice.
If it’s summer and you’re worried about getting hot, a pair of linen trousers can save the day. They are breathable and work for most settings.
If you have to wear shorts, choose structured ones, like chino shorts or tailored shorts.
6. Graphic Tees
Graphic tees are basically wearable opinions.
You can wear a graphic t-shirt to say what you like, what you support, and what you’re into.
I don’t wear them myself, but I admire people who are brave enough to express their opinions.
But they might not be quite a thoughtful choice for a first date.
The most obvious reason is that they’re too loud and pull attention away from your face.
Also, they can come off a bit too casual or even a little immature, especially if there’s a huge logo or a giant band member’s face.
What should you wear instead?
Plain crew necks always work.
If you want something a bit more flattering, try a V-neck.
And casual button-downs, especially linen ones, work great too. They’re relaxed, intentional, and way more first-date appropriate.
7. Chunky Shoes
Chunky shoes are not as popular as slim shoes, but there are plenty of people who love them.
Take my boyfriend, for example. He loves them, and they do look great on him.
So, why do they end up on this list?
They look good, but they also make a strong statement, which can draw too much attention to your feet.
Also, chunky shoes like oversized sneakers or platform boots often look clumsy and unkempt.
Most importantly, the big platform on chunky shoes can come across as if you’re insecure about your height.
Stick to clean, smart, and classic footwear. For example, clean leather sneakers, loafers, or Chelsea boots in a neutral color.
8. Tank Tops
Just like athletic shorts, tank tops give off a super casual vibe.
People often wear them for sleeping, going to the gym, or running out to a grocery store.
Wearing them on a first date can make you look lazy or sloppy.
Also, a tank top may seem a bit juvenile.
So, what should you wear instead?
Same advice as in the Graphic Tees section — plain tees, whether crew necks or V-necks, in neutral colors.
And if you really want to wear a tank top, just throw a linen button-down over it. You can leave it unbuttoned — still breathable but way more appropriate.
9. Chunky Jewelry
Just like big, flashy belt buckles, they look too loud and pull attention away from your face and straight to your accessories.
Also, they can be seen as a bit flashy and overdone.
So, what should you do instead?
Skip chunky jewelry and don’t pile up too many accessories.
Less is better. Wear one ring (a plain band or a signet), a thin 2-5mm chain, and, if you must, one low-key bracelet.
10. Funky Socks
Even though showing a bit of personality is good, funky socks can be too loud, just like graphic tees.
Also, they can come off a little immature or less serious.
So, what kind of socks should you wear?
They don’t need to be dress socks. Just wear simple, plain socks in neutral colors that match your pants and the overall outfit.
One more thing about socks: avoid wearing socks that are in high contrast colors with your pants, like white socks on dark trousers. They break the outfit.
That’s all, guys — 10 pieces I think you should avoid on a first date.
Hope you found them useful, and good luck on your first date.
One final rule: wear something that feels like you and matches the occasion.
