The first step of finding the best first date outfit ideas for men is to figure out what type of person you’re going out with, and mesh what her (his, or their) expectations might be with who you feel like you are. Of course, this process works better when you know the person you’re going out with at least a little bit before your date, but you can still assess your situation via online dating apps or the brief interaction you had before scoring the digits.
This look is good for just about any type of date and any set of expectations. You wear some casual chinos or dark denim and a fashion forward button down so you don’t seem overly dressed up or too under dressed. Pair your best and cleanest pair of sneakers with this ensemble, and you get the most versatile, comfortable, and clearly date-worthy of these outfit ideas for men.
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A great look for an art museum, an event, a concert, or any other art centered date, this outfit will keep you looking cool and feeling comfortable. Some men may stray away from longline shirts, but a tunic style top with some joggers, dark denim, or dark chinos is a fresh look that gives you both a sensitive air and a mysterious edge at the same time. Match your colors as seen below, or mic and match for more unbeatable outfit ideas for men. Neutrals prevent you from being too flashy and taking attention away from the event, and more importantly, your date. That being said, you do you man!
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No matter your counter culture, you might have encountered some dope floral button downs. The classic match up of dark florals and black denim only get better with your best beat-up pair of kicks. If you want your date to think “oh, he’s kind of cool though,” this is your look. Definitely don’t tuck in your shirt if you tend more preppy, but consider doing so if you’re on the opposite side of the coin. A hat never hurts ensemble either, but know thyself. No use trying too hard!
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First date outfit ideas for men can acceptably include sweatshirts if they are clean, mostly new or new, and paired with some other fresh pieces. I wouldn’t wear a sweatshirt to dinner, but for a game, a movie, or something else that you’ll be sitting during, your best sweatshirt is perfect. Definitely be sure to avoid ‘Saturday morning errands’ vibes and ‘too hungover to care’ vibes. Clean shaven or a beard well trimmed will show you put some effort in!
A sweatshirt is actually a great option for times you think your date might get cold because you can offer it for warmth. Just be sure to layer up so you don’t get too cold either, and perhaps avoid wearing a sweatshirt in a situation where your date might get cold if you don’t plan on offering it. Bonus points if your date takes your sweatshirt home that night!
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You know you’re fabulous, so why not let everyone else know with your own first date outfit ideas for men? If you know how to put together a look like no one else, or if you want to try, an outfit that shows your character best is always a good first date option. For so long I tried to ‘look my best’ on first dates; I still try to look nice, but now I also go out in what I feel most comfortable, confident, and myself in. It’s a balance of effort and ease.
If you’re a bit zany, don’t try to hide that on a first date because I’m sure your date will figure it out anyway. Mix your prints, colors, and textures, and your date will probably be impressed. If not, did you really want to date them anyway?
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For the guy who’s just not that adventurous in the fashion department, black on black with a basic white tee peaking out will give you the sleekest, sexiest, most simplistic of these first date outfit ideas for men. Choose clean sneakers, slick back your hair, and be sure to wear your sexiest watch (do you have more than one?). Leave that black button down undone so you give off a more relaxed vibe.
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Another for the black on black outfit ideas for men, this look is accented by a gorgeous character piece: a plaid coat. A black turtleneck is beatnik, timeless, and always so chic. Add some black trousers and a nice belt with a statement buckle to add some depth. The coat doesn’t have to be plaid, but should bring the color and the feeling of your character out. Bonus points if it’s vintage! Shoes are all on you, but with black you can’t really go wrong. A loafer would be the logical choice.
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A night out calls for some more fun outfit ideas for men, like an animal print tee and distressed denim. Ready to dance, rave, and salsa your date to disco heaven, this party animal is very cool and quite stylish in his crisp kicks. Also suitable at a theme park or for drinks at a club or trendy bar, the see-through raincoat is entirely optional in this look. Try surprising colors for your animal prints, or go with classic black and white. Stay away from this look if it feels less like fashion and more like most of your wardrobe.
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The best outfit ideas for men by the name of Mr. Practical, Mr. Stable, and Mr. Right. If you’re trying to get your date to see you as marriage material, you might consider wearing a suit… not casually for coffee, but for a nice dinner and perhaps a show of some kind. Extra points are given if you have the job to back-up this ensemble, and points off if you’re just wearing it to look cool.
Not every guy can pull this look off, but the outfit is more accessible without the jacket, tie, or if you swap the pants for dark denim. You can mix and match a bit here to find the right vibe for your date. Adding some fun socks shows your quirky side, so consider if your date might be into that!
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More excellent suit outfit ideas for men, but this time in a way more casual way. If someone showed up on a first date with me in a colorful suit with a white t-shirt and Doc Martens, the first impression would be excellent. The right balance of style, effort, and practicality, this look will be ideal for museums, botanic gardens, coffee shops, book stores, concerts, dinners, you name it. Change the color to change the vibe, and you have first date outfit gold.
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