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No matter how many times you hear it, it’s always worth a reminder: You only get one chance to make a first impression, and you’ve got to put your best foot forward with that one chance. That’s just as true in the frigid climes of winter, and it’s even more important as you dress for a winter date night.  Now, even if it’s not your first date, you still need to look sharp in every possible way with the right winter date night outfit. You want that winter date menswear look to really shine, reflecting your confidence and sense of style (again, no matter how many dates you’ve been on!). Here’s what we think just might be the best men’s winter date night outfit.

What is the Best Men’s Winter Date Night Outfit?

State and Liberty Howard Dress Shirt

Best Shirt: State and Liberty Howard Shirt

  • Comfortable, breathable stretch fabric
  • Flattering, tailored fit that works for broad shoulders
  • Visually appealing color
Mugsy Jeans Winston Jeans

Best Bottoms: Mugsy Winston Jeans

  • Classic jean design works for a variety of date night situations
  • Distinctive color
  • Extremely comfortable stretch fabric
New Republic Sonoma Suede Chelsea Boots 1

Best Shoes: New Republic Sonoma Suede Chelsea Boots

  • Timeless Chelsea boot design
  • Sturdy dress boot build for winter
  • Unique color
State and Liberty Grey Open Button Overcoat

Best Jacket: State and Liberty Grey Open Button Overcoat

  • Easy-to-layer fit and stretch fabric
  • Polished, tailored design for dressy date nights
  • Versatile color for winter style
True All Day Knit Golf Cleats

Best Sunglasses: Tomahawk Shades Wellsprings Sunglasses

  • Affordable price

  • Classic-yet-bold aviator design

  • Crucial UV protection from winter sun

Timex Marlin Automatic Watch

Best Watch: Timex Marlin Leather Strap Watch

  • Vintage-style look

  • Affordable price

  • A classy finishing touch with any ensemble

Fulton and Roark Solid Cologne

Best Fragrance: Fulton and Roark Blue Ridge Cologne

  • Subtle, handsome scent

  • Long-lasting fragrance

  • Designer-quality scent at an agreeable price

Best Shirt for a Winter Date Night: State and Liberty Howard Shirt

best shirt for a men's winter date night outfit It all starts up top with the proper shirt as you dress for a winter date night. In this case (especially if you’re venturing out to a cool speakeasy or cocktail bar), you want to go slightly more casual than your office look, but still crisp and polished. A well-fitting shirt in a deep shade of navy is flattering any day or night of the week, and this shirt boasts lightweight fabric to keep you feeling cool and comfortable. Every brand has a story and knowing the brand you’re wearing, makes you feel that much more confident. Find our more about State and Liberty or click the link below to buy now!

Best Bottoms for a Winter Date Night: Mugsy Winston Jeans

Mugsy Jeans Winston Jeans Dressing in style for a winter date night is all about projecting a relaxed, confident air (we’ve said it before and we’ll say it again), and a pair of nicely tailored yet supremely comfortable jeans help you hit a nice middle ground. Again, they’re more dressed down than an office look while still staying polished, and the brown color works nicely with a navy dress shirt.  Better still is the fact that the stretch fabric is supremely comfortable, not stiff, and the solid color is dressier than a pair of light wash jeans (save those for spring and summer dates). If you feel like you need to class things up, remember that Mugsy makes stylish stretch chinos, too.

Best Shoes for a Winter Date Night: New Republic Sonoma Suede Chelsea Boots

New Republic Sonoma Suede Chelsea Boots 1 For a stylish winter date night, we say step out of the snow boots and into something more sleek and streamlined. Classic Chelsea boots, with their dressy silhouette and on-trend appeal, are just what the style doctor ordered for a winter date night look. It’s all the better that these feature nicely textured suede in an eye-catching color that pops nicely against your brown denim. Plus, Chelsea boots are a dressy alternative to traditional lace-up dress shoes, one that shows you’ve got taste and personal style.

Best Jacket for a Winter Date Night: State and Liberty Grey Open Button Overcoat

best overcoat for men's winter date night outfit Your overcoat is one of the first things your date is going to see, and again, it’s all about stylish first impressions. Make a sharp statement with an overcoat that’s modern and streamlined, with a useful stand-up collar and tasteful open-button design. Plus, the crisp grey color pairs well with everything in your wardrobe – beyond just this winter date night look, and the fit is flattering with room to layer underneath. 

Best Sunglasses for Winter Date Night: Tomahawk Shades Wellsprings Sunglasses

Tomahawk Shades Wellsprings Sunglasses

Just because it’s winter doesn’t mean you should discard your sunglasses entirely. If your date starts in the afternoon and rolls on into the evening, for instance, stylish shades are crucial when it comes to protecting your eyes from bright winter sunlight. Best of all is the fact that a pair of affordable yet sleek sunglasses are yet one more way to show off your personal sense of style in a refined, memorable way. 

The accessories always make the difference, from shades to the watch on your wrist, so keep yours on point with a style that’s classic yet modern, and as fashionable as you are.

Best Watch for a Winter Date Night: Timex Marlin Leather Strap Watch

Timex Marlin Automatic Watch

Recall what we said about your accessories making the difference? Well, there are a few key things people tend to notice about your ensemble, starting with your shoes and yes, your watch. A winter date night is an ideal time to reach for a crisply designed, vintage-inspired timepiece that’s both refined and subtle without being too flashy.

And if you’ve slept on the watch brand Timex, now is the time to get back onboard: They’re designing plenty of throwback timepieces that look like something Don Draper might have worn, and in the case of this handsome leather-strap watch, that’s a very good thing indeed.

Best Fragrance: Fulton and Roark Blue Ridge Solid Cologne

Fulton and Roark Solid Cologne

Let’s keep it simple: Smelling great goes hand in hand with looking good, feeling good and “playing” good (or at least, putting your best foot forward on a winter date night). There’s no need to go too far overboard with your cologne, which is why a solid cologne is a nice change of pace from more expensive designer colognes. 

In this case, the solid cologne warms up over time when used in key areas like your neck and wrists, transforming into a handsome fragrance with rich notes of sandalwood and sage (two perfect scents for winter). Take care of the details with the best men’s winter date night look, grooming very much included.

Winter Date Night Outfit FAQ’s

How Should I Dress for a Winter Date Night?

Right off the bat, a winter date night should be treated like a special occasion, so we think that taking pieces you already love to wear – like Mugsy stretch jeans or chinos, and a polished State & Liberty stretch shirt – is a solid starting point. 

Yet, be sure to switch things up ever so slightly from the norm by using different colors and patterns for a look that’s crisp, casually cool and most of all, true to your sense of style. Case in point: Swap out your dress shoes for Chelsea boots, or trade a white dress shirt for a deep navy blue stretch shirt. 

What’s the Most Important Part of a Winter Date Night Look?

Dressing for a winter date night is all about rising to meet the occasion and the style situation at hand. You’re going to want to look for pieces that blend both functionality with style, so for example, you don’t want to be caught out in the cold without a handsome tailored overcoat. 

Beyond that, there’s perhaps not just one piece that’s the best part of a winter date night look, although a stylish watch or cool sunglasses for a late afternoon, pre-happy hour stroll are also nice touches to have. 

What Shouldn’t I Wear for a Winter Date Night?

As you dress on a brisk evening for a winter date (perhaps dinner and drinks, perhaps a night out at the theater or a visit to a cool cocktail bar), we think it’s best to follow the rule of thumb for wherever you’re headed. When it comes down to what not to wear on a winter date night, we say avoid wearing anything too casual – for example, a T-shirt probably won’t work at a fancy restaurant – or anything too formal (if you’re seeing a movie, for instance, avoid wearing a full tailored suit).

A good rule to keep in mind: Dress in clothing that’s comfortable, makes you feel confident and fits the situation stylishly. 

What’s the Best Look for a Winter Date Night?

If you think of an outfit for a winter date night as being filled with building blocks or foundational pieces, then the best men’s outfit for a winter date night is one that checks off a few key boxes. Again though, it’s crucial not to overdo it – or underdo it, for that matter. 

If we had to boil it down to the basics, assemble your stylish date night look in a manner similar to this: A crisply designed overcoat, followed by a stylish dress shirt (or a dress shirt and sweater), then add comfortable chinos or jeans, durable-yet-fashionable winter dress boots, and other accessories – like sunglasses and a cool watch.

Do I Need to Wear a Watch on a Winter Date Night?

Remember, the most important part of a winter date night is showing that you’ve put thought into the little things and the small details. If you’re a big-time fan of watches, perhaps wearing a timepiece feels like second nature and comes totally naturally to your daily ensemble. If you’re not an avid watch collector, or don’t normally wear a watch, we say go one of two ways: Consider trying out a watch that’s affordable, classic and stylish (like a  Timex watch), or else, stick to no watch if that’s not part of your normal look. 

The biggest key? Dressing in a fashion that’s true to yourself, comfortable and situationally appropriate. 

Where Is the Best Place to Go on a Winter Date Night?

This is entirely up to you, of course, but it’s always worth remembering that meeting your date in the middle – selecting a restaurant they’ve mentioned, tracking down a cool cocktail bar they might love, scoring tickets to a show or theater night – is a can’t-miss move for a winter date night. Just as with dressing stylishly for a winter date night, selecting an activity tailored to their interests (and yours!) is another way of showing you truly care. If you need specific date night recommendations check out our local guides.

Bonus points: If the date night involves a starry night stroll through a hip part of town, each of your winter menswear essentials will come in mighty handy.

Beau Hayhoe, the fashion guy, is our expert in all things men's fashion and grooming. Over the years Beau has written for some of the largest men's magazines and gained a deep understanding of the best brands, styles, and products for guys. You can catch Beau on his social media listed on his author page or by reading the rest of his catalog here on The Guy's List.

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