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7 Winter Date Night Outfits for Men

8 min

Do you need some quick tips and inspiration for what to wear on your next date? Fear not; you're in the right place.

The winter season often brings crisp, cold weather that requires several layers to stay warm and cozy. Of course, not every place on God's earth gets cold from October to February, but if you need some inspiration for layering up for those nighttime winter date nights, you've come to the right place.

Winter Date Night Essentials

My list of essentials may differ from yours but know that comfort is key. Sure, you want to look your best for your lovely date, but if you aren't comfortable, you won't enjoy your time with the woman you're with, and that is certainly no good.

So here is a quick list of what I recommend sporting for the date you have planned with that special lady in your life.

Cozy Sweaters & Knitwear

Look for soft, breathable materials like merino wool or cashmere. These fabrics will prove soft and sophisticated, adding elegance to your ensemble.

Choose a sweater that fits well and isn’t too bulky. Consider a turtleneck or crewneck for a classic look that flatters your frame (assuming you want to draw attention to it).

Numerous sweater options are available, including crewnecks, v-necks, cardigans, cable knits, and more. Choose something that reflects your personality and isn't too flashy. When in doubt, neutral colors are always your friend.

Warm & Stylish Coats

Always consider the area you live in. If it rains a lot, you'll likely want something to shield you from the elements. If it's below zero degrees Fahrenheit, ensure that your coat of choice is thick and hardy to keep you warm.

Invest in a high-quality, waterproof coat (if necessary) that will keep you dry and warm, whether a conventional overcoat, peacoat, or rain jacket.

Look for a coat with a fitted silhouette and a stylish design. Consider a long wool coat for a polished and sophisticated look. Don’t sacrifice style for warmth, though - look for a coat that does both!

Boots

Good boots are a staple in any man's wardrobe, especially for winter. Wear warm and stylish boots, such as traditional lace-ups or elegant Chelsea boots.

Consider wearing boots with good grip and traction to prevent slipping on icy sidewalks. For an extra layer of warmth, add a pair of warm and cozy woolen socks to your outfit (you'll thank me later).

To read our thoughts on the best boot brands available for men, see this article here.

Cozy Accessories

A set of dapper accessories has tremendous power. The great thing about the winter season is that it often affords men numerous options for accessorizing in unique ways.

For example, scarves are a great way to elevate any outfit and add sophistication and visual intrigue. Gloves can be another practical way of looking handsome while keeping warm, depending on the temperature outside.

And, of course, beanies are a great way to look cozy while adding much-needed warmth and comfort to your outfit.

Date Night Winter Outfits for Men

Outfit #1: Monochromatic Sport Coat

This look, reserved for more elegant and chic dates that don't require too many layers, is a textbook example of how to put together a dapper monochromatic look. Of course, monochromatic refers to using one type of color, and here, I am wearing all black with a medium gray flannel sport coat.

A turtleneck sweater is one of the most flattering types of sweaters a man can wear, and the black jeans and Chelsea boots create a clean look from head to toe. Of course, a little bit of contrast is good, so the sport coat in a lighter shade of gray is a natural choice for this ensemble.

This is great for cocktails or a high-end, cozy dinner with your date. Wear it, and you'll be sure to turn heads.

Outfit #2: Camel Coat & Black Turtleneck

Now, let's take the same outfit from the previous look and swap out the sport coat for something thicker and longer.

Here, I have exchanged the gray flannel sport coat for a long coat in a classy camel color. As you can see, the ensemble is decidedly more cozy but just as elegant as before. It is perfect for the same events as the previous outfit but better suited for colder climates.

Outfit #3: Mostly Monochromatic

For this look, we're returning to a monochromatic outfit with a few teaks this time. Instead of a turtleneck, we have a standard black crewneck long-sleeve t-shirt, and instead of a thick topcoat or elegant sport coat, I've opted for a charcoal herringbone-patterned car coat.

Although not quite as long and bulky as a topcoat or overcoat and certainly not as dressy as a sport coat or blazer, the car coat is a nice way to appear "dressed-up" without trying too hard.

I want to draw attention to my choice of footwear, though. I'm wearing dark olive suede chukka boots, which I think are the most versatile boots a man can own (yes, even over brown).

Read this article for more examples of how dark olive suede boots are the most versatile boot color for men.

Outfit #4: Smart Casual Topcoat

Layering for outfits is best done by starting with thicker layers on the outside and gradually working your way in with thinner layers. This outfit is an excellent example of that.

The outermost layer is a charcoal topcoat, which provides much-needed warmth for the brisk weather. The middle layer is a matching charcoal v-neck sweater, and the innermost layer is a blue gingham dress collar polo.

Gray and blue complement each other perfectly, but the oxblood boots steal the show, in my opinion.

For more fall and winter date night outfit ideas like this, check out my separate post here.

Outfit #5: Ultra Casual Topcoat & Sneakers

Despite my love for boots, living in sunny San Diego has taught me that not every day in December is a boot day. Don't overthink it; just make tasteful decisions!

In this outfit, I'm wearing a chunky cable-knit turtleneck, a charcoal topcoat, classic blue jeans, sneakers, and a ball cap.

If needed, throw on some shades, and you're all set! This is an excellent way to leverage those foundational pieces that every man should own when constructing his initial wardrobe.

A look like this is perfect for a cozy, relaxed, and laid-back vibe.

Outfit #6: Classic Navy Peacoat & Scarf

Overcoats, car coats, and quilted jackets provide warmth and elegance to any date night ensemble. Still, if you ask me, one of the most underrated outerwear choices for men is the classic navy peacoat.

Think of this as the "coat version" of a navy blazer because it can be utilized similarly. Here, I'm wearing a more smart casual outfit: a wool quarter-zip sweater, scarf, dark-wash jeans, and brown chukkas.

An outfit like this will have you looking like you walked straight out of a GQ magazine without trying too hard to look presentable for your date.

Adding a scarf to any thick coat is always a nice touch and will allow you to look even more put-together and sophisticated (trust me).

Outfit #7: From the Office

Let's take that navy peacoat and dress things up a bit.

This is a great way to look handsome for that special evening with your lady despite needing to go and meet her straight from the office.

Remember what I said about the navy peacoat being like the "coat version" of a navy blazer? Well, here is further proof of that!

This look meets the requirements for maintaining a business casual dress code while also remaining appropriate for your date (provided the venue/restaurant you're taking her to is more formal).

Forward-thinking, backward planning—it works in the military and everyday life! If you know that you'll likely be pressed for time between the end of your work day and the start of your date, account for this upfront!

Dress Well for the Occasion

Consider the activity and dress accordingly (such as wearing warm and comfortable clothing for a casual evening). Again, don’t sacrifice style for warmth—look for clothing that does both while enabling you to be the best version of yourself.

Be Confident (Never Arrogant) & Comfortable

Wear clothing that makes you feel confident and comfortable. Don’t be afraid to show your personality through your outfit (without going overboard). Remember, you can't ever take back a first impression! So bring your A-game.

Of course, confidence can quickly evolve into arrogance if we aren't too careful, which is never attractive.

Confidence means moving and walking with purpose and poise. Ahead of anything, it's achieving all of this while being respectful.

When we become arrogant, we lose virtually all the social grace we've worked diligently to build up and run the risk of even slipping into behaviors that can be considered offensive. Don't be this way!

Remember to Always Be a Gentleman

Creating a memorable date night outfit is about balance; it should be stylish yet comfortable for a winter night out.

Focus on texture and layering to create a handsome and cozy look. Layering darker tones of neutral colors can help you look more mature and put together, which will often communicate to the woman you're with that you are serious about dating her.

Now smile, open all doors for your date (even car doors), walk on the street side of her, and pay the bill in full. You're lucky to spend time with this woman and ought to treat her like gold!

The good news is that if you follow the advice in this post, you'll look like a million bucks and, more importantly, be a man worthy of being by your date's side. Be confident (never arrogant), and have a good time!

Now go and be the good man God fashioned you to be!

"He has told you, O man, what is good; and what does the Lord require of you but to do justice, and to love kindness, and to walk humbly with your God?" - Micah 6:8

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