Strap up gents, the holiday dating season is upon us. By now you probably know that this season is going to be jam-packed with a minefield of style-related situations, especially given you’ll hopefully be spending a lot more time (and money) going on dates and to parties with a special someone (special someones?). Since it’s stressful enough trying to coordinate the best times and days to go out, as well as the right venue, we figured we’d do you a solid and take some of the guesswork out of what to wear for a bunch of potential scenarios. That way you can keep your mind right and head into every date feeling confident-as-hell, knowing you're looking fresh.
With that said, we’ve broken down five can’t-fail looks that should impress the hell out of your date, regardless of where the night (or day) may take you.
Coffee and A Stroll
Super casual and a nice mellow way to hang, the right coffee date is a solid go-to. Get cozy and be sure to bring a lot of good questions and stories, or grab it to-go and throw in a walk to break up the interview session into something more relaxed. While we don’t encourage something as cliche as ice skating, we can’t promise you won’t get talked into it.
What to Wear - Casual but nice is key here. You want to find a balance between dressy (I give a shit) and casual (I’m not trying too hard). A wool bomber or peacoat, comfortable, dressy t-shirt or plaid button-up and dark chinos are a great way to stay comfortable and look sharp. Finish with boots or leather sneakers and throw on something with a pop of color, like your favorite scarf, and you’ve got the perfect conversation starter.
There’s nothing that brings two people together faster than working towards a common, charitable cause. You're going to show her you're a stand-up guy, plus, giving back is a gift you can give that really means something. Try to opt for something low-impact, like helping out at a soup kitchen or homeless shelter, but still be prepared to get your hands dirty.
What to Wear - You’ve definitely got bigger goals here but you also always want to remain stylish. A crewneck sweater or knit hoodie, t-shirt, and denim is the perfect vibe. Finish with a sharp pair of sneakers (not your gym shoes though) that stay comfortable from dawn 'til dusk. After a day like that, you guys probably deserve a cold drink.
Tree Shopping and Trimming
At some point, you might as well give in and go full-on holiday. So, if you and yours have graduated to the tree-shopping (or at least browsing) phase of your relationship, bundle up and get ready to, well, “debate” about why an 8-foot tree is “not a smart purchase”, whatever that means. Bonus points if you show up with two hot beverages too. And, while it’s certainly not mandatory, a little splash of holiday cheer (that means booze) in the hot cider, hot chocolate, or coffee never hurt anyone.
What to Wear - Dress for style and utility here; a wool peacoat, flannel or oxford, and denim or chinos are the way to go. Layer on a zip-up or v-neck sweater for extra warmth and go with desert or work boots as the footwear of choice. Remember that you’ll be moving from the cold outdoors to the cozy indoors, so layers that can be easily removed are your best bet.
Our never-fail first date, a relaxed drink after work is the ideal way to kick things off. But, it still demands some effort and finding the right spot. Even if it’s something casual after work hours, find a bar that’s a little quieter but still has a cool vibe. You definitely want to, you know, be able to hear each other, but also enjoy a proper drink. Hopefully, you read our First Date Cocktail Etiquette plan, and once your style is locked in, you’re golden.
What to Wear - No matter what your office dress code is, it’s important to make a few adjustments before you venture into the heart of darkness. If you’re rocking a suit to work, lose the tie and throw on a sweater underneath your suit jacket. Or, lose the matching suit jacket altogether and replace it with a blazer combo without a tie. Swap out your office captoes for loafers or monks for a fresh vibe. If your office is on the casual side, go with slim, dark denim, a dark sweater, and add one dressy element like a blazer or a tie. Elevating with one dressy piece is an unexpected move that really shows you’re confident in your style but not trying too hard.
Cocktails and Dinner
Tonight you’re pulling out the big guns. Whether you’re going to a classic mom and pop or an exclusive hotspot, this is the part where you turn up the nob and really put effort into looking just as good as the person you’re sitting across from. Wherever you go, make the night special and celebrate the holidays in style. For extra points, keep your date in the dark about plans, it’s a fun surprise. But just make sure you give her enough info about what you’re wearing and how she might dress so she’s not feeling under or over-dressed and uncomfortable.
What to Wear - This is a great opportunity to wear something sharp that stands out from the rest of the crowd, so don't be shy, dress to the nines. Throw on your boldest suit, a patterned or solid-color shirt, your best tie, and some dressier shoes, like a cap toe oxford or monk straps; they’ll make the perfect combination. The focus here is making a statement that’s impressive, yet complementary. You're not dressing for the boardroom or trading floor here so don't be afraid to take a risk or try something new, tonight's the night to do it.
The modern dating scene can be a beast, and doubly so during the holidays. So, if anything, take some solace in the fact that even if you strike out every once in awhile, at the very least, you’ll look good doing it.