How to Dress for 10 Different First Dates

Image via Complex Original

Look you’re going for: Clean and comfortable, but not couch-surfing wear

The traditional dinner-and-a-movie is the quintessential first date because you get to learn a lot about that person during dinner, from their current situation to their eating style. Then the movie gives you time to recap everything that just took place and assess the situation. But don't worry, she's doing the exact same thing, and one of those things she's assessing is how you decided to dress. Give her Ryan Gosling in The Notebook, not Blue Valentine. A casual button-down shirt, comfy chinos, and a medium-weight bomber or baseball jacket in preparation of the inevitable cold shiver she'll experience in the theater will let her know that you've carefully plotted out the evening just as much as the wife in Gone Girl. How you react to all the deception in that damn movie will also be on her mind, so tread lightly, my friend.

Look you’re going for: Like you may want to cover up that beer belly, in a stylish manner

You know that your date is an avid beer drinker based on the numerous pictures of her on Facebook holding a pint in her hand. So taking her on a quick jaunt to a local brewery will definitely impress her. And knowing what one should wear during a a brewery tour may impress her even more. Now, just because beer is involved doesn't mean that you should be dressing for this occasion the same way you would when you hit up your local dive bar. A sports jacket would be nice, but a slim sweater and a gingham shirt with a nice pop of color underneath will cover your top half. A pair of dark chinos to cover up any beer spills and a pair of blucher or beef roll loafers will make a perfectly stylish outing with your date. Or you can go the more casual route and throw on a clean flannel (depending on the time of year) and some form-fitting jeans, not the dad kind. And make sure you don't get so hopped up on the brew that you forget her name.

Look you’re going for: Like a fan, not a fanatic

The notion that "guys love sports" isn't a myth, but a guy who does love sports will generally only take a girl who also loves sports to a football game on a first date. There's a lot going on and not a ton of time to get to know each other, but the mutual respect of a team could bond two people better than a sit-down meal would. And your love for your team runs through your veins, but you can't come off like the die-hard fan that you are. Not on the first date. So leave the face and body paint at home and opt for your favorite player's jersey. Throwbacks are a plus for superficial aesthetic reasons only. As much as you want to wear your favorite cap, leave it at home because she will want to see your full features as you're screaming at the ref for not calling the holding penalty. Sneakers are a must, but a dirty pair that you don't care about, though logical, will not suffice for a first date. If you're willing to wear a nice, clean pair for her during a football, she's wondering what other things you'll do to try and impress her.

Look you’re going for: Stylishly dexterous while aware of the possibility of getting ratatouille on your shirt

They say that food is the way to a man's heart, but ladies take their meals very seriously as well. So a cooking class for both of you to try your hand at something new is a great way to learn each other's potential positive and negative traits. Starting with cooking, of course. But once you get knee-deep in that marsala sauce, you need to be cognizant of what you're wearing and how it can affect the whole date. Light colors around food, especially sauces, could be a potential issue with splashing or your overall clumsiness. Also, hovering over a hot stove or oven could cause more perspiration than you were expecting. A dark colored, breathable top with rollable sleeves will kill those two birds with one stone, while complementary trousers and comfy shoes, considering you'll be standing most of the time, will let her know that you think ahead and plan for certain situations accordingly. 

Look you’re going for: Like you are prepared for any kind of shift in the weather—for her, of course

Chivalry is not dead, especially when it comes to first dates, when you are trying to impress her with your knowledge and consideration for others. Taking a trip down the boardwalk allows you to walk, talk, play carnival favorites, and enjoy the sounds of waves crashing—all things you put as "loves" on your Tinder profile. You also enjoy being considered stylish, and that does not stop when you spend a majority of your time outside with ever-changing elements due to that large body of water beside you. Making sure that you layer up could be beneficial to you, but it will most definitely be beneficial to your date as she will require one, possibly two, of those layers to stay warm. Make sure all of your layers aren't heavy, though that may not be advantageous to your physique. A light-colored denim jacket with a crewneck is a potential piece that you’ll lose to your date, but keeping a chambray or flannel shirt and a long-sleeved thermal or baselayer around will also keep your body temperature regulated. She will forever be indebted to your generosity if she needs ‘em, and if she doesn't, losing a layer and tying it around your waste isn't the worst thing in the world. 

Look you’re going for: Like you understand that "casual" is a good look and "sweaty" is not

Taking a girl to a party on a first date could be considered sketchy on a lot of fronts, but when you have mutual friends and you'll both know people there, it's a great way to see how you get along in those types of situations with friends around. The heat will be on, though—literally and figuratively—and you don't want to funk up the date. Making sure that your clothing is breathable is key, so a plain T-shirt is a good, especially a dark blue one that will hide potential pit stains but won't attract as much heat as a black one would. Shorts are always dicey because too much man-thigh is enough to make anyone question a man's motive, but if you have a pair that sits right above the knee in a cool pattern to complement the tee, it could indicate that you're fun, but don't go overboard. Stay away from the flip-flops and opt for some slip-ons to complete the look that will keep you hot with your date while staying cool as the heat beats on the rooftop.

Look you’re going for: Like you’re an outgoing gent who cares, but not too much

You know you're about to go on a date with an outgoing, free-spirited individual and you want to show off your pipes—easy champ, we're talking about your singing ability. It's a great way to break the ice and to show that you don't take yourself too seriously. So you definitely don't want to dress like you're in a barbershop quartet or like a street performer. A nice sweater with a slim-fitting top underneath for layering will keep you warm whilst crooning "Cold As Ice." Slim black denim is basically a prerequisite if you plan on delving into "Thunderstruck," and a pair of Chelsea boots keep it classy as you air guitar and heel stomp across the stage. This basically leaves her without reason not to ask you to "Be My Lover."

Look you’re going for: Like you're ready to have a nice meal outside or ready to chase her dog around all day

Spending the afternoon outdoors in the park with your potential new wife (don't blow it, don't blow it, don't blow it!) could be a huge step in a relationship that hasn't even really started. A nice picnic is a cute and romantic way to have a meal, get to talking, and enjoy each others' vibes. You don't want her catching the wrong one with your attire, so a short-sleeved button down shirt, a pair of light-colored denim or chinos with a slight roll, and low-top canvas sneakers for a casual, comfortable look will prepare you for sitting on the cold, hard ground or for chasing after her Cockapoo that she brought along as an ice-breaker.

Look you’re going for: Like you can tell the difference between Krasner and Pollock, but in a non-douchey way

There's a fine line that you have to keep in mind when taking someone to an art gallery for your first date. You want to seem knowledgeable, but it's very easy to look like a snob whilst doing so. A great way to add to your savvy is to dress savvy with a casual two-button blazer—one without gaudy lapels—with a clean oxford underneath. Leave the bowtie at home, Fonsworth. A clean pair of suede or premium leather bucks, or informal wingtips, would set this fit to menswear aficionado, which, by proxy, is a prerequisite of art appreciation. And even though you won't have a good answer for your take on whether or not minimalist art is an oxymoron, you can still look like you know what you're talking about.

Look you’re going for: Like you’ve been to a concert before, basically

This is tough because you don't want to look #basic going to a concert when everyone is trying to out-stunt you, but you don't want to come off like you're trying too hard on the first date. You save that for the third date. No matter what type of show you’re going to go see, you can’t go wrong with classic concert attire. A leather jacket, slim denim, and boots comprise a look that has infiltrated all music genres and is still fashionably generous. She'll appreciate the edgy effort without going over it.