First dates can be stressful enough: between deciding where to go, trying not to drink too much, and keeping intellectually stimulating conversation, you don’t need the added stress of being unsure of what to wear. Your outfit, and the effort put into it, will convey more to your date than you may think, and if it’s your first date you want to send the right message. It’s a delicate balance between “I threw on whatever was clean” and “my mom picked this out”. Both are bad, so the goal is to fall somewhere in the middle. We know everyone has their own style, so we’re not here to tell you exactly what to wear. However, there are some universal tips that all men can appreciate. So even though it can be tough and nerve-wracking, we’ve got your back (and the shirt that’s on it).
Dress for the occasion
There isn’t one universal outfit that transcends all possible date spots (if there were, we wouldn’t need to have this conversation). Jeans may be acceptable for certain locations, while a jacket and tie may be required for others. This seems like a no-brainer, but you’d be surprised how often guys assume “date” is code for “black-tie affair”. Overdressing is as bad as underdressing - you don’t want your outfit to make your date uncomfortable with their own. Here are a few specific date examples that can be used as general guidelines.
CASUAL MEET UP: This includes the movies, heading to a low-key bar, hanging at one of your houses, etc. Jeans and a clean t-shirt are perfectly acceptable for these types of scenarios. Did I mention your shirt should be clean? Because your shirt needs to be clean.
UPSCALE DINNER: Not quite a black-tie affair, but you’re not going to McDonald’s, either. Opt for a nice pull-over sweater, or a blazer/sport coat/suit jacket (yes, they’re different), and you’ll likely be good to go. A dress shirt may earn you some points as well.
SOMETHING OUTDOORS: Going skating? Or taking a walk in a park? Or trying to win an obnoxiously over-sized teddy bear on the midway? Flannel works. A cool jacket does as well. A slouchy toque is even appropriate (if you’re into that sort of thing). This is a super casual date activity, so you can allow your outfit to reflect that.
BLACK TIE: I think you probably have a solid handle on this one.
Shower and deodorant are crucial for a first date, no ifs, ands or buts , but the trick is to have your fragrance say “I made an effort that went beyond my morning shower”. It doesn’t matter how good-looking/charming/smart you are: if you stink, we can pretty much promise you there will be no second date. But you also want to be sure your cologne doesn’t suffocate anyone. Choose a subtle, yet masculine fragrance (might I suggest something with sandalwood or otherwise musky undertones?), and put a few dabs on your wrist and chest. And no, you shouldn’t be able to smell your own cologne. Doing laundry is also an excellent plan. Your clothes should be clean, and should smell as such. Better your clothes have no smell than a bad smell.
Show your personality!
Despite what some may say, little touches that show your personality can be a good thing. Your best bet for achieving this with a subtle accent would be playful socks (with a more casual look) or a bold pocket square (if you’re wearing a suit). A cool band t-shirt under a flannel shirt or leather jacket is also perfectly acceptable in a casual setting, and can be a conversation starter if your date is also a fan. Just make sure there’s nothing frightfully offensive on it, especially if you don’t know them that well (should go without saying, but you never know).
It’s no secret: your shoes shall be judged. More people than you think notice your shoes during your day to day life, especially women, so a date is a full-on shoe judging festival. If you’re wearing a blazer/sport coat/suit jacket, dress shoes with a slim contour and slightly rounded toe is your best bet. Make sure they’re polished and properly laced to show you made that extra effort. If the date is on the casual side, anything goes…well, almost anything. Fun skate shoes or trendy boots are always a good call, but sandals and anything you wear to the gym are generally ill-advised.
Teeth brushed, facial hair under control, eye brows and nose hairs maintained. No one is suggesting that you need to go to a salon for a full-on body wax, but keeping your stray hairs in check is always a good move. You don’t need to stray too far from your every day grooming routine, but a little extra attention to detail never hurt anyone. If you are generally rocking the clean-shaven look (or if you know that your date isn’t a fan of scruff), shaving is a good plan - just be careful, because you don’t want to be showcasing your razor burn. If you’re of the hipster persuasion, or are just generally beardy, keep strays and frizz under control. A scented beard oil wouldn’t hurt either. Also, don’t pop any pimples the day of. You don’t want to be sporting a throbbing red bullseye on your chin, because yes, it’s noticeable. Bottom line, looking like you made an effort works wonders (bonus if it didn’t require that much legwork).
Don’t go nuts with the hair products
I know it’s tempting to overdo it ever so slightly with the hair products when you are trying to make damn sure your gorgeous style stays put. However, too much hairspray/pomade/wax can leave your hair looking crunchy, or greasy, or both. Tip: if you’re concerned about your hair products not working as well as you’d like, don’t wash your hair that morning. I know that seems counter-productive to not wash your hair on the day of your date, but day-two hair always holds product better than freshly washed hair. If you’re concerned about your hair smelling bad, don’t be. Skipping one day in your wash cycle is typically not enough to generate excess oil or an odour. You may be surprised with how much you like the texture, and will be pleased with how well it holds your style of choice.
Keep it fit
Your clothes, that is. It’s amazing how quickly a great outfit can go to waste if the fit is wrong. A jacket that’s too big, pants that are too long or sleeves that are too short will never go unnoticed, and that’s not the sort of attention you want. Fitted clothes scream “I’m put together”, which is precisely what you want on a first date. Keep your silhouette as streamlined as possible. Keep your wallet bulk to a minimum as well! Even if you normally carry everything you own in your wallet, keeping it to the essentials on a date is always good (cash, credit, ID).
Keep a hidden cache of emergency items
It’s always better to be safe than sorry, and this is why you should be prepared for any situation. Having gum on hand is a good start - especially if you’re nervous. Being nervous can give you a dry mouth, dry mouth equals bad breath, and that is a total mood-killer (obviously). Also a good thing to have for after dinner. If you’re driving, keep an umbrella in the car just in case. Having cough drops stashed away isn’t a bad call either - how awkward is a sudden coughing fit during a conversation? On that note, tissues should be around as well.
Clean your car! “Eau de gym bag” isn’t what your date wants to smell when they get in your vehicle. Clear out any fast food garbage, coffee cups, clothes, pet hair, etc. Maybe even run it through a car wash. This may sound like a lot of effort, but your car should probably just be clean anyway. No one (a date or otherwise) wants to get in your dirty, smelly car.
The phone stays out of the picture
There is nothing more rude than keeping your phone on the table during dinner with your date (especially a first date). Leave it in your pocket, and on silent, and only check it when your date heads to the bathroom. If you can’t spend a few hours away from your phone, maybe dating shouldn’t be on the top of your to-do list. This may not count as a style tip, but it’s certainly a general life tip. Also: make sure you don’t have your ring tone set to some obnoxious song. If you dohappen to get a phone call and the latest Pitbull song starts blasting from your pocket, you’ll send an instant shudder down your date’s spine. Silence is golden.
Just remember to show your date who you are through your style. Don’t try to be someone you’re not, because there’s only so long you can keep that up. If you’re uncomfortable in what you’re wearing, that will translate to your date. Be your amazing self, and we’re sure you’ll do just fine!
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