What to Wear for the First Date: 3 Outfit Ideas for Men

By Patrick Banks

Posted 1 year agoDATING

When it comes to matters of fashion, women seem to think that we guys have it easy. We just need to think about a top, put some jeans on, some shoes, and we’re alright. However, that’s not really the case. The lack of wardrobe choices is exactly the problem we constantly wrestle with. Because of this, we must heavily rely on two aspects: quality and curation.

While we really can’t help you with the aspect of quality, we certainly can assist you in putting together different outfits with finesse. This is what this article is going to be all about. We are going to share with you different outfit ideas that you can put together on your own and wear to set the best first impression on your first date. Let’s get started!

The Casual Comfy Day Look

This is ideal if you’re going out during the day for coffee, lunch, or a movie and you want to set an impression of being a down-to-earth kind of guy. Here are the elements you’ll need to put the outfit together:

Crewneck Tee

Choose one at a color that complements your complexion and eyes. Since it is only a crewneck tee, investing in a high-quality one should not be too expensive. 

Comfortable Shoes

When choosing a pair of men’s comfortable shoes, white sneakers, or loafers will do. Just keep in mind that whatever you do, don’t choose an open-toed pair. No proper lady will appreciate seeing your toenails, no matter how freshly groomed they are. Also, make sure that your shoes are clean. It shows a lot about your character. You’re down-to-earth yes, with a pleasing and comfortable personality, but you’re not a slob. You care. 

Slim-Fit Chinos

This will go well with your tee. Plus, it’s not a baggy bottom that exudes that air of over-confidence. Get one that fits you just right. It shouldn’t be too tight.

Denim Jacket

Finally, to tie your look together, put a denim jacket on. It will look effortlessly stylish, while at the same time, it will give you something to put around her shoulders during a cold movie or breezy walk by the beach.

The Calm and Collected Day Look

If you want to set the first impression that you are a guy with proper taste, intellect, and confidence, then this is the look for you. 

Knit Polo

Hence, instead of just throwing a tee on, we recommend wearing a knit polo instead. As much as possible, we recommend something of good quality but don’t be in your face with the brand names of your pieces. 

Don’t Forget Men’s Accessories

Show your taste through your choice of accessories instead, favoring craftsmanship over high-end brands. The best way to show that is through proper accessories.

  • Leather Wallet. To the discerning eyes, your choice of a leather wallet will tell a lot about your knowledge and taste. There are different men’s leather wallets to choose from, but we recommend something that’s handcrafted by a master artisan, preferably from Florence, Italy.
  • Sunglasses. Being able to choose a pair that matches your facial aspects perfectly will tell the lady that you are very aware of who you are and you’re perfectly confident with your looks. Just don’t make the mistake of wearing them indoors.
  • A Casual Watch. There’s no need to wear an expensive piece, but if you do have a chance to inherit a valuable heirloom, then that’s the best route to go. Since you’re just sporting a casual look, a timepiece with a leather band will suit your outfit best. 

Chino Shorts

This will balance the look. It will send the message that you are concerned about your looks but you’re not too uptight.

Suede Loafers

Finally, add a touch of style to your look with a pair of suede loafers. Why suede? It shows that not only are you not too uptight, but you also know how to have fun. 

A Dressy Night Look

Finally, if you want to take the lady out at night to a concert or a fancy dinner with drinks afterwards, then this is the look for you:

Wrinkle-Free Dress Shirt

You’d want a top that’s more resilient to wrinkling so you won’t have to worry about your outfit all night and actually have a good time. 

Straight Leg Trousers

It’s formal enough to make you look smart but it’s not too tight to hinder your mobility if you somehow find yourself required to move and dance. 

Leather Bike Jacket

A dress shirt and trousers? Your lady might think you’re boring. We can’t have that, can we? Hence, throw on a leather jacket and give your outfit some edge. Plus, let’s not forget that it will give you something to warm her up should the night grow cold.

Leather Shoes

Of course, your leather jacket would require a pair of leather footwear to match. We’ll leave it up to you to choose which one you want. You can go with dress shoes, chelsea boots, or whatever you find suitable for your personal comfort.


In the end, you just need to remember one thing when dressing up. It’s not the brands that you wear, but the pieces that you choose to wear. Each piece tells something about your personality. And whatever happens, don’t forget to groom yourself properly and wear a fresh pair of underwear just in case. Have fun!

About the author Patrick Banks

Patrick is a Berlin-based dating advisor, motivational speaker, a huge fitness and vegan diet enthusiast and the main editor at Wingman Magazine, specialised in men's health. His ultimate goal is to share with men around the world his passion for self-development and to help them to become the greatest version of themselves. He believes a healthy body and successful social interactions are two main keys to happiness.

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