Men’s First-Date Outfit Ideas

Confidence on a first date begins with feeling good about what you’re wearing. Learn how to dress for different occasions.

Man in a black suit with a red tie smiling.

What to wear

Trying to figure out what to wear on a first date? Regardless of your age, wear timeless clothes that fit you well. If you do this, you’ll look incredible.

First dates are important, and you want to portray the best of yourself. You want to make a great impression and show that you put effort into getting ready for the date. The key to dressing for a first date is to look effortlessly cool. This means that you look nice but natural.

Casual

The following are examples of what to wear on the first date in a casual setting:

Dark blue jeans and suede jacket

Dark blue jeans, beige shirt, green jacket, grey boots. — Photo courtesy of Everlane, Tommy Bahama, Nordstrom, and Reiss.

Denim on denim

Black jeans, grey shirt, blue denim jacket, black sneaker. — Photo courtesy of Nordstrom, Everlane, and Levi’s.

Jeans and a t-shirt

Grey jeans, navy blue shirt, grey sneakers. — Photo courtesy of Nordstrom and Everlane.

Smart and business casual

The following are examples of smart casual first date outfits.

Jeans and a button-up

Jeans, button-up, loafers. — Photo courtesy of Nordstrom, Eton, and Trask.

Chinos and sweater

Chinos, sweater, Chukka boot. — Photo courtesy of Bonobos and Nordstrom.

Chinos and sportcoat

Chinos, button-up, sport coat, loafer. — Photo courtesy of Bonobos, Nordstrom, and Allen Edmonds.

Formal

The following are examples of formal first date outfits.

Blue suit

Charcoal grey suit

Grey suit, white button-up, blue tie, black Chelsea boot. — Photo courtesy of Nordstrom and Johnston & Murphy.

Black suit

First date tips

Now that you know what to wear on a first date, the following are 5 tips to help your first date go smoothly.

1. Safety first

Safety is always important, but especially if it’s with someone you haven’t met in person before or have only met once. A great way to ensure your first date runs well is to have your first date in a public place with other people around.

2. Ask genuine questions

Conversations can begin with small talk, but don’t let it stay there. If you continue to talk about the weather or what they ate today, chances are, you won’t feel a deeper connection. Ask genuine questions to get to know the other person on a deeper level.

3. Be firm with boundaries

Everyone has personal boundaries, and it’s important to maintain them. You want to feel safe and respected while dating without any pressure to do something you don’t want to do. This also goes for the other person; you should respect their personal boundaries.

4. Know what you want and need

What do you want from a person? What’s your intention with dating? Yes, you want to make a great impression, but you also want to make sure the person is a good fit for what you want. You may need to go on more than one date to figure this out, but don’t let a good impression cause you to be someone you’re not.

5. Enjoy the moment

A first date can be stressful, and that makes it easy to forget to be present. Being nervous, worried about what you’re wearing, or what the other person thinks is normal. Overcome those thoughts with a reminder to enjoy the moment and have fun. Even if it doesn’t work out, by having a good time, it’ll be worth it.

Conclusion

By knowing what to wear on a first date, you can now focus on preparing for the date. Enjoy the moments, be present, keep boundaries, and have fun.

David Em

Founding Editor

David Em is the Founding Editor of Next Level Gents, a men’s lifestyle blog. Since 2018, David’s mission has been about helping men build confidence through style, fitness, and grooming. He lives in Kansas City with his wife and daughter. He’s passionate about men’s fashion, cycling, and cooking.
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