Men's Date Night Outfits That Put Your Best Foot Forward

You're going to want to copy these ASAP.
Men's date night outfit ideas
Photos, from left to right: Urban Outfitters, Todd Snyder, Percival
tres dean Associate Menswear Editor
Tres Dean
tres dean Associate Menswear Editor
Tres Dean
Associate Menswear Editor
  • Tres writes and edits articles for The Knot, with a specialty in menswear and suiting.
  • He brings over a decade of expertise in the field garnered as a writer, editor, copywriter, and trend specialist.
  • Before joining The Knot he covered menswear for publications including GQ, AskMen, Men’s Health, Sharp Magazine, Highsnobiety, and Spy.
Updated Mar 15, 2024
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Looking to put together a great men's date night outfit? It's a lot simpler than you'd think, though I don't blame you if the thought alone has your head spinning. Whether it's a first date or a night out with your partner of a decade, worrying about what to wear is natural. I'm here to make it a little easier on you–both for the date you have in mind and any date moving forward. Plus we've got some insight from The Knot's very own assistant fashion editor Sofia Deeb. She'll be the first to tell you that the real secret to a great men's date night outfit is a little bit of effort. Read on to learn the best way to apply it and to get some fitspiration for your next night (or day) out.

In this article:

How to Choose a Men's Date Night Outfit

Putting together the perfect date night outfit can seem like mad science. Calculating the right shirt to wear with the right pants, how to accessorize them, and whether or not sneakers or dress shoes are the right call can drive you insane–but it doesn't need to. "Your date night outfit should reflect your personality and your own unique sense of style,' Deeb suggests, "Especially if you're just getting to know each other." You don't need to dress outside of your comfort zone. You just need to consider the circumstances of the date, the impression you want to make, and how you want to put in that little bit of extra effort.

  • Dress For the Date You're On: This one might seem redundant, so let me clarify: if you're going out for a lowkey coffee, you don't need to wear a suit. Date nerves (especially first-date nerves) may push you to overdress. Don't fall down that path. If you're going on a casual date, you can dress a little more casually. On the same note though, if you've got a table at a restaurant that requires a reservation, you should dress up a little more–overdressing isn't great, but neither is underdressing.
  • Stick To What You Know: Dressing for a first date doesn't require you to step outside of your sartorial comfort zone. As far as Deeb is concerned, your favorite band tee can have a place in your fit as long as you style it the right way. This is where that bit of extra effort can work wonders. "It might seem a bit too casual," she says, "But layering it with a more structured corduroy or flannel shirt can completely level up its look–plus it can serve as a conversation starter."
  • Avoid What You Don't Know: Deeb also notes that dates (especially first dates) aren't always the best time to experiment outside of what you're normally comfortable with. "Chances are, if you do that, you won't feel like yourself," she says, "And your date just might take notice of that." I'll personally attest to that part–any time I've ever gone on a first date and worn something that felt more like a costume than an outfit, there hasn't been a second date. First dates especially tend to come with all kinds of nervous vibes as is. Don't give yourself one more (unnecessary) reason to be anxious when getting dressed.
  • When In Doubt, Layer It Up: Okay, admittedly this advice might not go over as well on a hot August day, but consider this: wearing layers on your date gives you built-in options should you need them. Is the restaurant a little chillier than you anticipated? It's not a problem if you wear a light jacket or overshirt–you can always take them off if you don't need them. Is your coffee date going so well that you decide to take a walk? Again, if you have layers on deck you're ready for it. Layers help you stay ready so that when the time comes you don't have to regret not already being ready.

Men's Date Night Outfits To Copy or Shop

Whether you're going for a fancy night out or a quiet night in, a good date night outfit is a surefire way to get your date off to the right start. Remember, a little effort goes a long way, so here are some of our favorite date night outfits for you to copy or just take a little inspiration from.

For a (Fancier) Dinner Date Night

Men's fancy dinner date outfit
Jacket: J. Crew,Pants: J. Crew,Shirt: Eton,Loafers: Morjas

You don't have to go full black-tie attire for a dinner date, but whoever you're going with will appreciate it if you go the extra mile with a suit and dress shirt. Wear the look with loafers for a fancy (but not too fancy) finish.

For a Wine Tasting

Men's wine tasting date outfit idea
Jacket: Brooks Brothers,Shirt: Todd Snyder,Pants: Madewell,Loafers: Morjas

You should still dress on the nicer side for a wine tasting but you can leave the suit at home–a nice button-down, solid trousers, and the right jacket and loafers are all you need. Just be careful not to spill–red wine stains are a pain, after all.

For a Karaoke Night

Men's Karaoke Night date outfit
Shirt: Urban Outfitters,Tank: Dandy Del Mar,Pants: Percival,Shoes: Reebok

When going out for karaoke, make sure you bring the right fit to match your showmanship (and on that note, don't forget your showmanship–nobody likes a stick in the mud when everyone else is giving it their all). You can stick to casual staples for this, like a trendy plaid shirt with cool pants and some classic kicks.

For a Hike

Men's hiking date outfit
Shirt: Buck Mason,Pants: Huckberry,Hat: Huckberry,Shoes: Huckberry

Dressing for a hike can be tricky–you want to have the right clothes for the occasion, which means functional, but without giving up looking fashionable entirely. Some sturdy but stylish hiking boots, a tough knit tee, and a good jacket can be the secret to nailing this fit.

For a Night Out Dancing

Men's dancing date night outfit
Shirt: Percival,Sunglasses: Akila,Shoes: Amberjack,Pants: Banana Republic

Like hiking, this is a fit you want to make sure looks great while also being fit for the occasion (in this case, a whole lot of movement). For this one, try a knit polo with a fun pattern, plus pants that give you room to move and comfortable shoes.

For a Beach Day

Men's beach date outfit idea
Shirt: Urban Outfitters,Shorts: Dandy Del Mar,Shoes: Sabah,Sunglasses: Macy's

Trendy swimwear, a trendy shirt, and a great pair of shades are all you need to show up looking your best for a beach date. Throw in a pair of slip-ons so you won't have to walk back to the car barefoot.

For a Picnic

Men's picnic date outfit idea
Shirt: Huckberry,Jeans: Levi,Necklace: Miansai,Shoes: Vans

Picnics can make fur the perfect romantic afternoon. When it comes to getting dressed for one, try a western shirt with some reliable blue jeans and a pair of easygoing kicks to cap it off.

For A Theater Date

Men's Theater Date outfit idea
Jacket: Huckberry,Shirt: J. Crew,Pants: Kit Blake,Shoes: Beckett Simonon

Going to see a show or musical? Make sure to dress accordingly with a nice button-down, trousers, and shoes to match. Your date will thank you.

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