12 Stylish First Date Outfits for Men (Women Love #5)

by | Nov 12, 2019 | straight men |

You can’t afford to not make a strong first impression

The date is set. You did it, man! You got up the nerve to ask the pretty little lady that’s been on your mind, out on a date. But now you’ve got to figure out what to wear on a first date.

For many, asking out a woman is the hardest, most nerve-wracking part of this entire process. It’s all serenity from here on out.

first date outfit for men

Until you realized, you don’t know what to wear on your first date.

That’s the whole reason why you’re here.

And I’m here to help guide you through every step of the way of picking out the perfect outfit for your first date.

But first, before jumping into outfit ideas, there are a few things we need to address that will directly affect your outfit decision.



How to Decide What to Wear on a First Date

There are many components that go into deciding what to wear on your first date. Where are you going? Are you wanting a second date with this person? What’s your own personal style?

There are many questions to be asked before choosing your first outfit, and you want to make a great first impression on this woman, I’m sure. And intimidatingly enough, according to scientists from Princeton University, it only takes about 1/10th of a second to form an opinion about someone.

There’s no time to waste. You need to make a strong, great first impression when your date lays eyes on you. Your clothes will speak for you before you even open your mouth, so choose wisely.

Date Location

Your date location is going to directly coincide with your outfit decision. No one wears a suit to a coffee shop at noon, whereas similarly, you don’t want to wear ripped jeans and a simple tee to the fanciest restaurant in town in the evening.

first date outfit for men

If you’re choosing the date location, then it’s going to say a lot about your personality. Of course, you want to choose a restaurant that will impress her(if you plan on having a second date), but you also want to feel like yourself and comfortable when going on this first date.

No one wants to feel unnecessarily uncomfortable on a first date. So pick a place where you’ll be impressing her, but you can also dress in a way that you feel most comfortable and like yourself.

So once you decide whether you’re going to a fancy restaurant and you’re going to dress it up, or a nice little coffee shop or family-owned restaurant where you can wear an everyday outfit and just spice it up, then we can talk about what you’re going to want to wear.

Personal Style

Listen, you do not want to pretend to be someone you’re not. 

This goes for many reasons, but think about this. You show up to your first date dressed like someone you’re not and in a way that you’re not comfortable, but your date is digging it.

Your second/third date comes along and either you have to keep changing who you truly are for this person, or you’ll show your real self and the other person is out.

first date outfit for men

Or it could go totally vice-versa. You might miss your dream-girl because you were pretending to be someone you’re not, and she doesn’t like this persona or front you’re putting up.

So what I want to encourage you to do is this: Be the best version of yourself on this date.

If you like to wear casual outfits, just accessorize a little and put in the extra effort. If you like to dress it up, then do just that, just make sure your outfit matches the occasion.

Still wondering what to wear on a first date? Don’t worry. We have loads of examples on what to wear on a first date coming up in a jiffy.

First Date Outfit Ideas for Men

So as a man, what should you wear on your first date? Let’s consider the weather: will it be hot or cold outside? Are you going to a restaurant or are you going hiking? Let’s go over some 3 options for any of these possible scenarios.

Casual First Date Outfit for Mens

These 3 casual first date outfits are perfect for a lunch date, an early evening out-to-dinner, or even an evening walk through the town. These outfits feel like you put in the effort, but you didn’t try too hard. Check em out!

Casual First Date Outfit Option #1.

first date outfit for men

Outfit combination: A simple sweater with a jean jacket thrown on top, white fitted-jeans, dark brown shoes, and a watch.

This outfit says “I’m professional, yet a good time. I thought about this outfit, but not too hard.”

You match, you look nice, and your date will notice and appreciate the effort you put into this outfit full of neutral colors.

Casual First Date Outfit Option #2.

first date outfit for men

Outfit combination: Dark denim fitted-jeans, light denim button-up with a mustard knit sweater thrown over top, and of course, a watch. For shoes, if you want to continue a casual vibe, you could wear a pair of Vans or any white sneakers. You could also dress it up by wearing some oxfords or casual dress shoes.

All of these pieces are pretty much staples of anyone’s closet. You can recreate this entire outfit with any fitted-jeans and button-up. Layering your clothes is a huge yes, especially during chilly seasons. If it’s really cold outside, pair this outfit with a scarf and coat.

Casual First Date Outfit Option #3.

first date outfit for men

Outfit combination: A pair of pants cuffed at the bottom or rolled up, a short-sleeved button-up, a watch, a necklace, bracelet and watch.

This outfit is simple, and that’s why you can play so much with the accessories. He didn’t go over the top with them, though. The accessories are subtle, and all are in the same color family. Stick to all silver or all gold for aesthetically pleasing results.

This outfit is perfect for any warm day for a walk around or coffee date.

Fancy First Date Outfit for Men

If you really want to woo your date and take her somewhere fancy, then you need your outfit to match the tone of the place you want to take her. Here are three fancy first date outfits.

Fancy First Date Outfit Option #1.

first date outfit for men

Outfit combination: White fitted-jeans, A light-blue button-up with the appropriate number of buttons undone (which is 2-3), A brown sports coat, a watch, and leather shoes.

This outfit is fancy, yet still casual, in a sense. It doesn’t feel like you’re about to go to a fancy wedding, but it does say “I’m serious about this and you.”. The perfect fancy date night outfit.

Fancy First Date Outfit Option #2.

Of the 12 outfits in this article this is the look that the ladies we polled found like most. While it’s on the fancier side, if you live in a metro area you may be able to pull it off on more casual settings.

You’ll have to be comfortable with this look for it to work, of course.

first date outfit for men

Outfit combination:  Grey and white plaid dress pants, brown leather shoes, matching leather belt, white button-up, bracelets and watch.

You could definitely add a grey or navy sports coat to dress this outfit even more, but this outfit is perfect for a warmer day.

Fancy First Date Outfit Option #3.

first date outfit for men

Outfit combination:  White button-up, grey vest, colorful handkerchief, dark jeans, and probably black or brown leather dress shoes.

This outfit is as manly as it is fancy. It’s perfect for when it’s too warm outside to wear a coat on top. The handkerchief gives this neutral outfit the perfect amount of color to stand out.

First Date Outfit for The Movies

Going to the movies is always a safe option for a first date. It’s casual, fun, and you automatically have something to talk about after the movie is over. Here are three perfect first date outfits to wear to the movies.

The Movies – Date Outfit Option #1.

first date outfit for men

Outfit combination:  Grey ripped jeans, grey t-shirt, black leather jacket, white sneakers, brown pack-pack.

We all know that the movie theatre is a little bit chillier than it should be. This is the perfect opportunity for you to show off your chivalry. Wear a jacket to the movies and when she’s cold, offer your jacket to her.

The Movies – Date Outfit Option #2.

first date outfit for men

Outfit combination:  black skinny jeans + slim chain, black boots, black tee, brown suede jackets, and watch.

The suede jacket here is the key piece to the entire outfit. It gives it just enough color to make the all-black outfit stand out. It’s a classic outfit and is still stylish.

The Movies – Date Outfit Option #3.

first date outfit for men

Outfit combination:  black ripped skinny jeans, white t-shirt, open button-up, white sneakers.

This outfit is so simple, yet very nice. It’s the perfect casual outfit, but you still look put together. The ultimate lazy boy outfit. Everyone, literally, everyone has all of these pieces in their closet. It’s just all up to how you pair and style them.

Sporty First Date Outfits for Men

Maybe you and the girl you asked out are a little more active than the average person and want to do something different, like hiking, rock-climbing, or going to play mini-golf or frisbee. There’s a way to look nice and sporty. Here are three outfits for you to be inspired by for your outdoorsy date.

Sporty First Date Outfit Option #1.

first date outfit for men

Outfit combination:  Black sweatpants with white stripe, black simple tee, watch, sunglasses, and black and white sneakers.

This is a prime example of how to be ready to run around and be sporty, while still being fashionable. Find some dressy sweatpants and wear some nice, clean sneakers, and you’re set.

Sporty First Date Outfit Option #2.

first date outfit for men

Outfit combination: Green sweatpants, grey t-shirt with cuffed sleeves, a sporty watch, a bracelet, and white sneakers.

Another way to style a simple t-shirt and change the entire look of it, is by simply rolling up the sleeves. By doing this, it looks like you put more effort into your outfit. It’s such an easy trick that spices up your entire look and it only takes a few seconds to do.

Sporty First Date Outfit Option #3.

first date outfit for men

Outfit combination: grey shorts, long green tee, white sneakers, and a cap turned backward.

A simple outfit like this needs to be accessorized. A hat, a watch, a bracelet, or anything will make this outfit look 10x better and will show that you have a sense of style and that you put some effort and thought into making a simple outfit look better.

Final thoughts

Before closing out, I just want to say a few more things.

Sometimes, it’s not about the clothes you wear, but how they fit you. The same shirt in two different sizes will look completely different on you. Don’t go too tight that it looks too small on you, but not too baggy that it looks like it’s a size too big.

Be well-groomed. Trim your beard, get a last-minute haircut. Show her you care about how you look and take care of yourself. By caring for yourself, you show that you’re capable of caring for others as well.

Be safe. If you’re meeting (or thinking about meeting) an online date, make sure you do a little background check on them to make sure they’re legit. DateID can help you know who you’re meeting a little bit better. It may even help you come up with ways to dazzle her with great first date conversation topics.

And most importantly, be yourself. Confidence is everything. You could have all the knowledge and money in the world, but not have a good time with your date because you’re not confident with who you are. Have fun, let loose, be you, and enjoy your first date. Read more of our best online dating tips for men.

I hope you found these idea on what to wear on a first date helpful. Let us know in the comments which outfit was your favorite and what you’ll be wearing on your next first date!

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