6 Men’s Winter Date Night Outfit Ideas

Whether it’s grabbing dinner at a favorite bar and grill, checking out a new club or seeing a movie, you want to look your best for your date. In the winter season, the goal is to wear clothing that’s both warm and stylish. The good news is you have lots of fashionable possibilities to choose from. Read on to discover our favorite winter date night outfit ideas.

Outfit Idea #1: Henley, Jeans and Chelsea Boots

One of the best things about a long sleeve henley is that it’s both comfortable and fashionable. Plus, this shirt looks great with a pair of jeans.

Channel a blue theme with your outfit by wearing a light-blue henley with a pair of dark blue jeans. A pair of Chelsea boots in gray or brown suede would be a good choice for this outfit.

If you prefer jeans in light blue denim, try pairing them with a dark brown or deep red henley. Slip on some Chelsea boots in chestnut brown or burgundy to echo the red or brown of your shirt. Your boots, combined with the style of your shirt, keep this outfit casual while delivering a trendy look.

Outfit Idea #2: Tee, Bomber Jacket and Dark Jeans

A jacket will help keep you warm on a date night in the wintertime. Go with a classic look by slipping on your favorite white tee with a pair of dark denim jeans. Then, put on a reversible bomber jacket in black. A pair of dark suede boots looks sharp with this outfit. White sneakers are a good option if you want to go in a more relaxed direction with your footwear.

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You can put a different twist on this classic by wearing a v-neck burgundy tee or a slim fit tee in navy blue with a green bomber jacket and dark denim jeans. Black or brown boots are two suitable options for this look.

Outfit Idea #3: Button-down Shirt, Jacket and Pants

This next idea combines a sharp button-down shirt with a pair of pants and a jacket. Try looking for pants in different types of fabric to change up this look.

One option is to wear black chinos, a heather gray button-down shirt and a black denim jacket. A pair of black or gray high-top sneakers suits this look well.

For a date on an especially cold winter’s night, a pair of wool pants is a nice choice. Consider a pair of charcoal-gray wool pants with a blue denim button-down shirt. For a finishing touch, put on a black wool overcoat. Having a well-made pair of wool pants in your wardrobe can help you look polished, even for a casual date.

Outfit Idea #4: Sherpa Jacket, Black Jeans and Boots

A denim jacket with a sherpa collar and lining puts a fun new twist on a traditional favorite. As a bonus, this jacket provides extra warmth while enjoying a date on a winter’s evening.

A black denim jacket with a white sherpa collar looks dramatic when put with a pair of black jeans, a black tee and black boots. If you want to lighten up this outfit a little bit, then substitute your black tee for a white one.

A light blue denim jacket with a white sherpa collar looks good with black jeans, too. You can add a little more interest to this ensemble by wearing a plaid shirt. Black and red plaid or blue and gray plaid are both attractive choices. Chestnut brown or tan boots pair well with this look.

Outfit Idea #5: Tee, Sport Coat and Jeans

Start this outfit with a pair of dark denim jeans and a tan or white tee shirt. Complete this casual date night ensemble with a navy blue sport coat. Wear a sport coat with a subtle black and blue plaid pattern if you want to add more interest to this look.

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A heather gray wool sport coat worn with dark denim jeans and a black tee offers an elegant look, especially when worn with black boots. A cashmere scarf gives this outfit an extra dose of style.

Outfit Idea #6: A Button-down Shirt, V-neck Sweater and Chino Pants

A button-down shirt worn with a v-neck sweater and chino pants creates a warm and classy look for a winter date. Furthermore, the variations of this outfit are only limited by your imagination.

A royal blue button-down shirt, a smoke gray v-neck sweater and a pair of light gray chino pants make for a sharp outfit. Choose a pair of black or dark gray boots for your footwear.

If you feel like putting a little more color in this ensemble, then start with a v-neck sweater in blue. Pair it with khaki chino pants and a pale blue button-down shirt. Brown boots are a cool choice for this combination.

A v-neck cardigan sweater with buttons is another variation to consider. Wear a gray v-neck button-down cardigan with a white button-down shirt, along with a black tie. Try this combination with black chinos for a modern look. Be sure to button up your cardigan so you can tuck your tie into the top of it.

This look works with a button-down cardigan in navy blue, black or even dark green. Throw in an extra dash of style by rolling your shirt sleeves to the elbow and folding them over the cuffs of your cardigan. This simple detail highlights the look of your button-down shirt.

Express Your Cool Weather Style

These are just a few examples of outfits that are perfect for going on dates in the cold weather season. Changing up the colors, fabrics and footwear styles in these examples can help you put your own spin on a cool date night outfit.

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