winter date night outfits, winter date outfits

13 Winter Date Night Outfit Ideas for Men with Cool Styles

In our opinion here at Perk, winter dates don’t get enough of the spotlight. Winter is a great time to go out on a date, as there are plenty of winter date outfits that will stun and impress your significant other! 

When it comes to winter outfits for date night, you’ve got to think about two things: looking good and staying warm. We promise, both are possible if you know how to dress.

Dressing well for your first date outfit in winter is crucial. After all, your clothes put across your first impression, and you want to make sure it’s a good one! That’s why winter date outfits should not be glossed over simply because “they’re going to be covered with a coat anyway.” That is no way to think! Conversely, you should think about how you can incorporate your coat into your winter looks for men. 

We want to make sure that your winter date night outfits look good, because your partner should understand that you put some effort into looking nice. Let’s get into it.

A First Date in Winter

Before you start shopping for cool winter outfits for guys, get intel on whether the venue you’re visiting is indoor or outdoor, as this will have a big impact on the clothes that you wear. Once you figure that out, you’re free to start configuring your winter outfits for date night. 

For a first date, pick something that you’re comfortable wearing. It might not be the best time to bust out the brand new pair of jeans if you’re not settled in them yet. Instead, you might try for a classic (and classy) khaki pair of chinos from Perk. Especially because you know they look good! 

Outfit Ideas

There is tons of variety available regarding winter date night outfits. Here are a few main contenders to choose from:

  • An Oxford shirt 

  • Wearing an oxford shirt for a dinner date outfit in winter is the perfect way to look put together and sleek. If you slip on a crew neck sweater over it, your look will come together perfectly. 

  • Knitwear

  • You want knitwear that gives your look the edge it’s looking for, and something classy enough to blend in at the bar should you decide to head there after. Pairing knitwear with good chino pants is never a bad idea, either. 

    If you’re looking to make a statement, keep the rest of your outfit simple and let your knitwear do the talking. 


    There are a few winter accessories that you can’t go without, and those are coats, scarves, and hats. You don’t have to wear all of them together, but there are plenty of ways that you can mix and match or help them shine on their own. 

    If you choose to wear an oversized scarf, you can be sure that your neck and chest will stay nice and warm. This also allows you to keep your overcoat open and flaunt the layers that you’ve put on, whether it’s a t-shirt and a blazer, a sweater, or a button-up. 

    Just make sure to pick a color that either contrasts with your outfit or complements the colors. You don’t want something that’s too close to the shade of your coat or shirt. Hint: if you’re wearing dull colors, go for a colorful scarf. If you’re wearing solid colors, go for a patterned scarf. There are tons of options available for winter casual outfits for guys. 


    Layering is another big-time need for the winter, as there are so many different ways that you can make it work. You could place a sweater over one of Perk’s fine tops, or try something different like a vest and a turtleneck together. 

    Bomber jackets are another great way to layer. They’re super stylish and you can layer them over almost anything and, on the bottom, the pants are up to you. Whether you choose jeans or chinos, bomber jackets are versatile and comfortable, and many see them as a staple for a man’s winter wardrobe. 


    Cardigans are another great option when it comes to layering, since they can be casual or formal. There are so many options out there, which can be both a blessing and a curse. Choices are always good, but it can be hard to know what to pair your cardigan with - but we’re here to tell you that they look good with jeans, chinos, and even dress pants. Try out different looks to see what you like best! 

    The Winter Dating Scene

    The most important part of a winter date is making sure that you and your partner have fun. We’ll leave that part to you, but we’ll take care of the fashion advice! If you need more of it, you know where to go