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.