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Share to PinterestMen's Date Night Fashion Tips That'll Slay

Men's Date Night Fashion Tips That'll Slay

By Staff Writer
Share to PinterestMen's Date Night Fashion Tips That'll Slay

You finally asked that cutie from the office or campus out on a date. The anticipation is building, and you want to check all the boxes, including looking sharp enough to secure another hangout.

A well-thought-out outfit can boost your confidence and make you feel like a million bucks. We have a closet's worth of suggestions for various outings so you can put your best foot forward.


Relaxed lunch in town

Share to Pinterestman wearing denim jacket

You can't go wrong with a classic denim jacket, a crewneck tee, slim-fit chinos, and a pair of sneakers, preferably white. This combo is great for spring and early fall weather and comprises must-have basics from a capsule wardrobe.

Make sure the t-shirt is crease-free and doesn't look faded, yellowed, or stretched out.


A ball game

If your date's keen on sports, score some tickets to a match. Provided you're well-dressed, you might just score away from the stadium, too! Combine a non-patterned button-down shirt with a comfortable sweater vest, slim jeans, and leather slip-on. Or opt for a white t-shirt and black track pants and bust out your exclusive Air Jordans.#mentra


Beach bod

Going to the beach but not into the water? Don a knit collared golfer, a pair of chino shorts, and suede loafers. If you're pulling a Baywatch and jumping in the ocean, match your tank top or t-shirt to your swimming trunks, place a baseball cap on your noggin, and don a pair of aviator sunglasses.


Culture vulture

Off to a play or museum? A dress shirt underneath a light sweater looks sufficiently smart casual, especially when the collar neatly peeks out. Select straight-leg trousers or jeans. And if you want to up the ante or it's a bit cold out, a tailored blazer never hurt anybody.


Clubs and dancing

Are you planning on going for informal drinks or to a club? A biker or bomber jacket that's not cumbersome allows you to move comfortably while looking sharp, and slim-fit ripped jeans are still all the rage.

Check the club's dress code. Your footwear can range from boots to dress shoes. Leave the top couple of buttons open on your casual shirt.



We've got two words for you—double denim. Couple a soft denim shirt with a complementary but slightly darker pair of jeans. Wear Chelsea boots to add a hint of sophistication. A modern watch is always a good idea, and as a bonus, it helps make sure you make it on time.


Cold mountain

Are you into the gorpcore trend where streetwear has taken a decidedly alpine bent? If you have no clue what we're on about, have a look at A$AP Rocky and Frank Ocean's looks of late.

Get yourself high-performance items like a North Face jacket, a Patagonia fleece, and Salomon ski boots. Even maximalist puffers are having a moment if you can pull off a bold look. Finish the ensemble with a beanie.


Hike up the style factor

Share to Pinterestman hiking dressed in windbreaker

Heading on a trail for your next meetup? Gorpcore might cause you to overheat in all the wrong ways, but you can still pivot from city style to an outdoor adventure aesthetic. Comfort is key. Prepare for out-of-the-blue rain showers and protect your limbs from insect bites and thorns.

Choose sweat-wicking pieces that fit well without being too tight. Merino base layers are great, and a sleek windbreaker is essential outerwear. Jogger sets help you look put together, too. Trail runner shoes or hiking boots finish the look.


Netflix and chill

When things heat up, and you're inviting your gal or guy over for a Netflix and chill sesh, your loungewear gets a starring role. Your favorite hoodies can come out to play, as can your flip-flops. And this should go without saying, but you'd be surprised how often it's not the case: make sure your undies of choice are a fresh-out-the-laundry kind of clean.



It could be cold when you have a first sleepover, in which case, sleeping in your birthday suit might not be an option. Pajamas are making a comeback, gents, so, consider swapping your hole-ridden sweatpants and alma mater T-shirts for modal fabric, spandex-blend drawstring pants or shorts, woven flannel, or linen sets, and a robe.

A silk set with an oversized T-shirt silhouette can look fantastic, too.


Festival flair

Music festivals are great opportunities to be playful with your sartorial choices from head to toe. Opt for an unbuttoned Hawaiian shirt with a sleeveless tee or bare chest underneath, and pair it with cargo shorts or trousers.

Tie-dye, bold prints, and bumbags are welcome here. Pick crease-resistant pieces that keep you comfortable the whole day, and pack a waterproof lightweight jacket.


Dinner plans

If you're going out for a nighttime meal, pick a spot where you can flex a dark monochromatic look with a black jacket, black t-shirt, black jeans, and black boots.

Not everyone can pull this bad boy aesthetic off without looking cheesy. But if you hit the right note and combine swagger with gentlemanly behavior, there's a good chance you'll be the dessert.


Winter fashion

Fashion-lovers rejoice when the seasons turn frosty because the clothing options are chef's kiss. Make the most of the cooler temps with debonair peacoats, turtlenecks, cashmere scarves, and sweaters.

It's all about the layers. A flat cap à la Tommy Shelby from Peaky Blinders can keep your head warm. A beanie or fedora might work better if a newsboy hat doesn't suit your look.


Put-together but low-key

Here's another option to show you're stylish in casual settings. Go for a horizontal-striped sweater if you want to look broader and vertical lines if you'd like to elongate your torso. Wear a plain oversized shirt-jacket over the sweater, and put on some flattering jeans and sneakers sans scuffs.


Meet the parents

Things are getting serious and you've been invited to a family gathering. Keep the occasion in mind. Is it a Fourth of July barbeque or are you a plus one to a family wedding? For the latter, you can go suited and booted. Matching tailored plaid wool trousers and a suit jacket over a crisp white shirt can show you mean business, at least in the fashion department.

An alligator belt, suede shoes, and a luxury timepiece are the cherries on top of this cake and are sure to get Mom's stamp of approval.


Hot to trot

Now, about that summer barbeque—here's a winning combo. Wear a print button-up shirt with fitted short sleeves paired with chinos or shorts, and high-tops or oxfords. Or elevate a henley shirt with fitted jeans and a sports watch. Think hands in pockets casualness and ease that, when done well, elicits all the flame emojis.



Share to PinterestMen's accessories organized on table.
fstop123 / Getty Images

Accessories are the bomb dot com. They take your clothing to the next level, and sometimes a look isn't complete without them. Just make sure you aren't overdoing it—when in doubt, less is more.

Sunglasses, socks, belts, jewelry, ties, and classy wallets are worthy additions to your fashion arsenal. Since they aren't essential basics, consider saving up for better quality and longevity.


Grooming FTW

Share to PinterestClose-up of hairstylist's hands cutting strand of man's hair
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What you wear will matter very little if you show up with bad breath, body odor, or a generally unkempt appearance. No one wants to see ketchup on your tee, friend.

Visit a trusted barber before a first date to get your hair and beard, if relevant, in tip-top shape. Consider the locale when you decide if a light spritzing of cologne should top it all off.


Consult someone who knows better

Share to Pinterestman trying on new denim jacket with stylist in modern boutique
Westend61 / Getty Images

We all have that one friend or family member whose looks are always on point. If you're close to someone with the kind of style you'd like to emulate, ask them to go shopping with you. Or if you're not sure which clothing items in your closet work best together, get them to assist you.

Don't have one of those people in your life? While you're looking for one, let us help: a fashion aficionado will likely advise you to buy long-lasting neutrals and age-appropriate attire.


Be true to yourself

Share to Pinterestman wearing leather jacket and sunglasses
SanneBerg / Getty Images

Understand who you're going out with and what they might expect of the occasion. You need to strike a delicate balance to avoid being under-dressed or over-dressed and to prevent your date from feeling the same.

Ultimately, your fashion choices should elevate the mundane, tell a story that's uniquely yours, and make you feel suave, whether it's Valentine's day or a regular Sunday. Remember, if you don't feel comfortable in what you're wearing, you won't look it, either.



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