A Guy’s Guide: What To Wear On Your First Date


As guys, we can agree that it’s difficult to pick what to wear on a first date, so let’s get down to it.

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We’re gonna do like SpongeBob and party ’till we’re purple on this first date. No one is like you and that’s why you have all the reason to enjoy yourself. As a 23-year-old who has been on several first dates, I’ve learned that the more excitement you approach a first date with, the more comfortable you will be with yourself. Part of being yourself includes feeling like yourself. I want you to stay within your means as you dress yourself on this first date. Stay within your budget and style to stay you.

We don’t play games when we go on our first dates. We’re going to try very hard to look good, but we’re not going to show it. I’ve labeled four possible settings for your first date. I will not include every conceivable location, but you CANNOT GO WRONG with any of these combinations.

Classic Steakhouse Vibe

The classic steakhouse means you’re at a place where you will look out of place if you show up in khakis and an untucked button-down.

Pants: Dress Pants. Make sure you have a pair that fits you. Buckle your pants so they do not crimp around your waistline. If they do, and that is your only pair of pants, your date will notice. If you’re willing to buy a new pair that will fit you nicely, Macy’s, or your local department store, will have inexpensive dress pants that will fit you.

Top: Dress shirt. Iron it. Even if you just buy it from the store and you do not have to wash it, there will be hella creases on it. Iron that sh*t.

Tie? Nope. This is the epitome of trying too hard. This does not mean, however, that you will flay your shirt open for your date to see your chest. If you are not worried about sweating through your shirt, you do not have to wear an undershirt. You can pair this with a blazer if you’d like. As long as there is no tie, that is not trying too hard, in my opinion.

Shoes: Wear formal leather shoes. A lot of guys make the mistake that Sperry’s are formal shoes. They do not have to be $180 Cole Haan kicks. Dust-off a pair of leather shoes and make sure your belt matches that color.

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A Guy's Guide: What To Wear On Your First Date

Casual Sit-Down Restaurant Vibe

This is a restaurant that you had to get a reservation for, but the people go there all the time in t-shirts.

Pants: Chinos or khakis. Chino’s are like cooler looking khakis. If you do not have a pair, khaki’s are great. I do not like the jeans vibe for a sit-down restaurant, they’re too informal, in my opinion.

Shirt: You have more wiggle room here. Wear a button-down or a sleek long-sleeve. I prefer the sleek long sleeve because it shows you are not trying too hard. The long sleeve will fit well when you complete your look with your hair slightly gelled and a fitting pair of shoes. If you wear a button-down, only keep it untucked if the shirt hangs at the level and not below your crotch. Too saggy of a button-down shirt shows laziness.

Shoes: The same as the classic steakhouse vibe shoes: formal leather ones.

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A Guy's Guide: What To Wear On Your First Date

Bar/Ice Cream Store Vibe

Pants: Jeans or chino’s. Please, no khakis. Don’t have jeans or chinos? Khakis are still an OK choice, but if you are willing to purchase a new pair and can afford a ~$100 pair of pants, visit BananaRepublic.com for form-fitting (this doe snot mean slim) pants. Form-fitting means when your date (and they definitely will) look at your butt and legs, they notice you tried, but not too hard ‘cus your shirt and shoes are casual.

Top: This matters on the season. If it is winter, I prefer long sleeve. If we are in spring, you can go tee shirt or short-sleeve button-down. Whichever you choose, make sure it isn’t too tight. Muscle guys (me being one of them) unfortunately, girls will not fall in love with you just because of your muscles. Your confidence and conversation abilities have to be up-to-par first.

Shoes: Be careful here. Women always look at your shoes and just because you are in more of an informal setting does not mean you can relax with the footwear. You can whip out some desert boots, athletic shoes, boat shoes or even leather winter boots.

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A Guy's Guide: What To Wear On Your First Date

Coffee House/Outdoor Activity Vibe

The coffee house and outdoor activity vibe is one of your few excuses to wear whatever you want. Each setting brings with themselves many informalities that encourages you to do the same with your outfit. Wear jeans, a tee and your beat-up Nikes. You want to feel comfortable moving around and just being yourself.

Need more direction? Don’t feel comfortable dressing down? Wear the Bar Vibe attire.

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A Guy's Guide: What To Wear On Your First Date

Step outside of your comfort zone to feel more you on your first date.

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