Men's Date Outfit Ideas for Winter

You have a date, and you couldn’t be more excited. Unfortunately, the weather is an obstacle. What’s a man to do when going on a date in cool weather? How do you remain stylish and comfortable while also fighting off the chilly temperatures? We’ve put together some men’s date outfit ideas for winter that will help you achieve the best of all worlds.

Keep It Simple with a Quarter Zip


We’ll start with something simple and clean—something that wouldn’t only work in winter, but could work across any season when the weather is crisp. In this outfit, we’ll pair a simple Quarter Zip with the clean, put-together look of military twill pants. This will give you a relaxed, casual vibe that still shows off the fact that you put some thought and effort into how you look.

Start with the Drop Needle Quarter Zip Black. This quarter zip is casual without being lazy, and smart without being stuffy. It hits that ideal middle ground—you don’t want to overdress or underdress. And it doesn’t hurt that this is the kind of comfortable top that will help you feel at ease, which is exactly what you need for a date in the first place.

Pair it with a contrasting color. We recommend Military Twill Classic Fit Fatigue. The grayish and olive tones here are a classic, but will help differentiate you from anyone else wearing khaki or blue.

Warm Up with Corduroy and Fleece


Here’s the good news about date outfits during wintertime—you have a lot of opportunities to add some texture and contrast to your outfit. That’s hard to do when the weather’s so hot that your only options are shorts.

We recommend getting started by adding a Polar Fleece Vest to your wardrobe. You can throw this vest over just about anything—including a button-down—if you want to dress smart for your date. But you can also keep it casual depending on the setting.

Pair it with Stretch Corduroy. The charcoal color is just a suggestion, but really any color will do well here. The idea is to highlight the fun contrast of the fabrics, giving you a put-together, cozy winter look.

A Classic Look for Winter


What if you don’t just want to invest in an outfit for a date this winter? What if you want to have an outfit ready for every winter? Then it’s a good idea to invest in clothes that will be versatile enough to look great in just about any season—or any year.

We think the two outfits above still fit the description, but we’ll leave you with one more recommendation for versatile cold-weather. Consider wearing a Drop Needle Henley and Classic Vintage Twill in light Khaki. These are the types of items that won’t only look great on a date, but will fit with just about anything else in your wardrobe for years to come.

Shop Selections from Berle

We hope you’ve enjoyed these men’s date outfit ideas for winter! If you want more great clothes to wear for date night, browse our Vintage 1946 collections to find items that will help you feel and look your best.