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What To Wear On A Casual First Date For Guys - 8 Outfit Ideas

What to wear on a casual first date guys - Jasper Holland Co

First dates can be tricky in so many ways. While there’s always the potential that you’ll have a fantastic time, there’s also a lurking fear that you’ll be trapped in a nightmare. Either way, though, you’ll want to look good.

So it’s good that at least the wardrobe part can be easy. Nobody wants to show up on a casual first date overdressed. But at the same time, your old Vans, faded t-shirt, and jeans from the 2009 era just won’t do. Every guy knows this, no matter how much of a style coma he’s in.

So, how to solve the conundrum of showing up looking casual on a first date but also like you don’t live in a tent under the bypass on the edge of town? Don’t overthink it — we’ve got your back. These eight ideas are your solution to the what-to-wear-on-a-casual-first-date style dilemma guys sometimes have.

1. The Minimalist

 What to wear on a casual first date guys - Jasper Holland Co

Plain and simple may be your motto, but your minimalist style need not be either plain nor simple. There’s nothing plain about a gorgeous white t-shirt paired with simple khaki pants. White is a color that complements any skin tone and the one in our example above is perfect because it has just enough design to make it interesting without wrecking the minimalist vibe you’re going for.

The watch is by a Scandinavian brand known for its minimalist design ethos (think Ikea for watches). The jacket is simple and stylish but also intentional — not just something you threw on because it was chilly outside. It lends a polished vibe to an otherwise very basic look so don’t overlook the jacket component of this look.

Who knew that a white t-shirt could give you such a classy look? Apparently Jasper Holland did. The casual yet classy white tee is the perfect undergarment to pair with the jacket.

The pants are All-American khaki updated with a tapered skinny silhouette. Don’t make the mistake of donning a pair of office pants or the whole effect is totally nerdified — in a bad way. And they should be worn with white sneakers because otherwise, well, sloppy.

And here’s where it gets interesting: the sunglasses. As the sole representative of outfit creativity here, they should be far-out and fascinating, just like you.

Here’s where you can sport the minimalist look:

  1. The Gaming Date. If you’re lucky enough to have an arcade in your town, and you’re lucky enough to have met someone who’s open to spending time at one, you’re… well, one lucky guy. The minimalist look is easy enough to handle (not too many accessories) for an action-packed date.
  2. An Amusement Park. Nothing says “fun first date” better than an amusement park. Better yet, make it a retro amusement park: the kind with kids’ rides, popcorn, and old-timey games that involve a little bit of skill. Your hands-free minimalist outfit is perfect for jetting around on the grounds in search of the best ride in the park.
  3. Bowling. Again, the hands-free aspect of the minimalist outfit is wonderful for action-packed first dates.

 

2. The Pilot

 

We’re all aware of the allure of Tom Cruise in the 80s — if not on a first-hand basis then surely you’ve heard of the effect that the Pilot look has on women. For the 21st century, it’s important to get the details right so you don’t end up impressing just the Kelly McGillis crowd but hopefully women your own age, too.

The Pilot is casual and 100 percent identifiable as wholesome and masculine — almost to the point of seeming conformist. But as you’ll see with all the looks here, the difference is in the details.

So what’s different in the Pilot look some thirty-odd years later? Two things: what you wear underneath the leather jacket and well, what you wear underneath. In other words, it’s a) the pants and b) the t-shirt.

Let’s begin with the t-shirt.

If it’s a t-shirt that you keep coming back to for all of life’s biggest moments, fear not: it’s completely appropriate to wear one on a first date. With the right one, you can look great without stepping out of your comfort zone. The look here requires a t-shirt designed for a grown-up. This is not a bro t-shirt. Nor is it one you’ll want to toss in the corner after wearing, only to scrounge around for it three weeks later to wear to a round of stickball or a quick gym sesh. It’s a nice t-shirt, one which looks curiously like you’ve ironed it before stepping out (but of course you haven’t). And by the way, this applies to all the looks you’re about to see.

Once you’ve got the grown-up t-shirt right, the leather bomber jacket is an easy addition. Go for crisp, new leather or distressed leather — whatever speaks to your sensibilities. Next up will be the pants- skinny will plant you firmly in the 21st century. Don’t go too skinny or you risk a top-heavy balloon look due to the volume of the average bomber jacket. In other words, keep an eye on the silhouette you’re making.

With all that in mind, here are three first dates where you can totally be The Pilot and make a great impression.

  1. The Dive Diner Date. This is all about balance. Since you’re meeting your date in a downscale arena that’s about as casual as it gets, you’ll need to up your game style-wise. That’s why The Pilot works so well for a date to a dive diner. It’s casual and masculine enough to look tough in case a brawl breaks out but with the upscale details that you just learned about, impressive enough to be date-worthy at the same time.
  2. After-Work Meetup. For after-hours dates, the darker the palette, the better. And let’s assume you’re meeting at a place with a little swank to it — the kind of place that serves hand-crafted cocktails and champagne. The Pilot works here because the beauty of leather jackets is that they can always be dressed up or down. Your choice to pair yours with finely tailored plaid pants and a sophisticated set of manly accessories (watch, slip-on boots, etc) means you’re perfectly dressed for the poshest of spirit houses.  But since it’s nighttime, you just may want to leave the aviator sunglasses at home.
  3. Anywhere That Requires Driving. We just can’t help ourselves here. There’s something so very attractive about a man driving a car and wearing a leather jacket. It speaks of adventure, worldliness, capability and, because of the Tom Cruise reference — skills. Wear the Pilot look driving and it really doesn’t matter where you’re going.

3. Nerd Chic

 Casual date clothing guys - Jasper Holland

Thanks to the tech revolution of the past twenty years and the rise of the coolness of Silicon Valley, we now have Nerd Chic. Guys (and girls) now have the option of dressing to their intelligence. In other words, you no longer have to choose between looking smart and looking cool. Nerd Chic accomplishes both. Brains are always attractive so you’ll want to give this look a try.

The key to accomplishing successful nerd chic is threefold:

  1. The jeans. You’ll need crisp jeans. And by that we mean they should be pressed, they should be dark rinse, and the inseam should be perfect so that the cuff falls just over the top of your shoe.   
  2. The t-shirt. Since this is a very simple and unfussy look, the t-shirt must be spot-on perfect. No fading, no stretched-out neck, no signs of wear at all, actually. We suggest a light gray color that shouts “tech”, which of course dovetails nicely with the whole nerd aura.
  3. The watch. Watches are no longer the sole purview of the nerd class. These days, everyone wears them so it’s important to get the right one. Not too flashy but tech enough to supplement the idea that you’re really smart. Or just really nerdy. Either way, the watch we’ve featured here is perfect. It’s basic black with lots of complex knobs and it shows all kinds of extra data, way beyond just the time of day.

Here are three date ideas where your Nerd Chic look will win you points in all areas.  

  1. The Saturday Afternoon Meetup. Nothing says “casual” like a Saturday afternoon date. It takes the pressure off both of you since more often than not, this is a time reserved for lounging around in your PJ’s alone at home. No time wasted and you’re not monopolizing someone’s Friday night, the all-important slot for socializing with friends or coworkers.

It’s also a great time for nerd-chic activities like visiting a museum, riding a bike around town, or kicking back and grabbing coffee at a cool cafe… all of which make perfectly acceptable first dates.

  1. The Dog Walking Tour. If you both have dogs, then you can both kill two birds with one stone: get the dog out for some exercise and spend a fun time on a first date. This gives the added benefit of seeing if your date is compatible with your dog. It’s also the perfect opportunity to play up the nerd thing by wearing an awesome pair of nerdy, classic sunglasses.
  2. The Aquarium. Visiting a large aquarium (if you have one in the area), is a great way to grease the wheels of conversation, and get to know each other in a fun, casual setting. A win-win all around. The extra win for you is getting an up-close look at the sharks and stingrays without letting her know how excited you are about it. You wouldn’t want to give the impression that you’re an actual nerd.

 

4. The Floridians

 Casual first date outfits for men - Jasper Holland

Jetting away together to a warm locale for the weekend isn’t your typical first date scenario. You know- too risky. But if you’re a risk-taker (or if it’s hot where you live), there are two ways you can go. Miami Cool or Key West Hot.

Miami cool involves — yes, wait for it — a blazer with rolled-up sleeves. Before you channel too much Miami Vice, however, note the 21st-century details of the look we’re suggesting. For starters, there are no pastels. Just for good measure, repeat this twelve times before choosing what to wear: Do. Not. Wear. Pastels.

Instead, get a blue blazer. It’s soooo very 2019 and, more importantly, it’s a manly color. Plus, it works in so many different situations you’ll be glad you got one for future dates.

The Key West hot look doesn’t require a blazer but it’s just as important to get the deets right. The keywords here are: sharp. Pressed. Clean. Crisp. The khaki shorts/t-shirt look can quickly become the ‘old man/hippy/doesn’t care’ look if you don’t get the details right.

So here’s what you need in order to avoid the bum look: tailored shorts from a high-end brand, spiffy shoes, a fedora, and a classy t-shirt worthy of being featured in GQ (not High Times).

Here are three date ideas where you could rock these warm-weather looks.

  1. The Chill Dinner. Since a first date can be a minefield of miscommunication and sweat-inducing mistakes, it might be good to plan for an indoor location. That way, you can keep sweating to a minimum even if it’s hot out. Seek dinner or lunch at a place with strong AC, cozy seating, and a fun vibe. The Miami Cool look is perfect for this setting.
  2. The Neighborhood Stroll. Daytime dates are tons of fun but tricky. You never know whether you’ll be hanging for just an hour at lunch or spending all afternoon together exploring what the world has to offer. The Key West Hot look allows you to play it safe with comfortable shoes that won’t raise eyebrows in a fancy establishment in case you decide to hit one up after your stroll. A stroll in the park can easily lead to a marathon of visiting book stores, art galleries, ice cream parlors, and who knows. You’ll be glad you wore shorts and good shoes.
  3. The Outdoor Sports Event. So, you both love sports. This is a no-brainer date idea. But first dates can bring on the sweats even if it’s frigidly cold outside. And here you are planning on sitting outside under the sun with your date. The good news is, everyone will be sweating, including your date. The other good news is, you now have a great-looking t-shirt that you can wear to show her you care enough to dress sharp — even when it’s a million degrees outside.  

5. Scholar

 What to wear for date night guys - Jasper Holland

Not to be confused with the Euro look, the Scholar is all about comfort. Don’t fear the cardigan. Cardigans are all the rage these days. One reason is the styles are form-enhancing: with the big collars and chunky knits, they have the effect of bulking up your upper body. The key to making the cardigan look great is a nice form fitting t-shirt with muted colors.

And essential to getting the scholar look just right is the jeans. They must be slightly faded. Because scholars are too absorbed in their scholarly work to stand for stiff, dark jeans that show dirt. Again, it’s all about comfort. Hence the suede chukka boots, the no-fuss watch, and high-end comfy socks.

Here’s where to sport the Scholarly look:

  1. An Art-House Movie. We don’t typically suggest seeing a movie on a first date but art-house movies are different. You’ll need to assess whether your date is a good fit for seeing an art-house movie. The great thing about this as a first date is that it gives you both a lot to talk about afterward.
  2. Some Crazy Obscure Foody Place. Don’t just go for dinner. Go for something totally new so you can both explore new tastes together. Never tried Korean? Moroccan? Now’s a good time to go for it.
  3. A Teaching Moment. Hey, you’re dressed for it so why not? If your date has some special skills like photography, ask them to give you a simple lesson. And remember that “skills” is a loose term. Their skill could be mastering Fortnite and this would still work.

6. The Urban Athlete

 Casual date outfit ideas men - Jasper Holland Co

We know you: you’re athletic and you’re in shape. But aside from showing up for your date in head-to-toe Under Armour gear, how can you show your physical prowess and your taste for movement without coming off as a cad?

Introducing the “Urban Athlete” look. The first thing you’ll notice is that you get to wear sneakers and a nice t-shirt. The second thing we want you to notice is that it’s not just any pair of sneakers and not just any t-shirt.  

The sneakers should hail from the upper echelons of style — a limited edition set of Nikes fits the bill, for example. And the t-shirt must absolutely be a styled shirt, not a square with armholes. The fit should be slim but not tight, no matter how much you want to show off your Bowflex body.

The shirt in our example look hails from Jasper Holland, which produces a sublime specimen that dresses up nicely with crisp lines and sharp-looking edges. A far cry from your old faded, stretched-out rags that should probably be thrown away.

Here are three good date ideas for the Urban Athlete:

  1. Ride Bikes Around Town. If you’re game and they are too, cycling around town in some cruiser bikes is a sure-fire way to get some laughs.
  2. Catch a Comedy Show. Speaking of laughs, you can get a good sense of their sense of humor at a comedy show. Even if the talent is bad, the atmosphere is rife with opportunities to make your own jokes and see how it goes. After all, if they don’t laugh at your jokes, then how long is it really going to last?
  3. Hit a Bookstore. There’s nothing sexier than an athletic guy who likes to read. Plenty of opportunities to bond over rare book finds and coffee afterward.

 

 

7. The Euro

 Guys date night outfit ideas - Jasper Holland Co

Warning: this look requires panache and confidence because let’s face it — American guys don’t usually wear scarves. But if you’re game and it seems like your date might be inclined to favor the Euro vibe that you’ll be giving off with this look, go for it.

The star here, of course, is the scarf. Worn loosely and nonchalantly around the neck, it tops off an otherwise straight-laced outfit that might otherwise be mistaken for office attire. The other essentials of this look include a natty jacket, unusual leather shoes, and a worldly pair of sunglasses that indicate you may just be a world traveler in your spare time. T-shirt is the army green heather Grid design from Jasper Holland.

Here are three date ideas where you can sport The Euro look:

  1. The Aquarium. The ambiance of an Aquarium is perfect for a first date. It’s peaceful, soothing, and quiet enough to be able to talk and get a sense of each other’s conversational skills. Plus, you get to gauge their attitude toward animals, if that’s important to you.
  2. A Ferry Ride. The ferry ride is perfect because now you have a reason to don the sportscoat and scarf. Plus, the half-hour or so it takes for the average ferry ride is just enough time to get to know someone without investing too much time in case it all goes south. 

8. The Dark Side

This is certainly one of the dressier silhouettes on the list, but hey if you’re going to be anywhere near an art gallery, this is the look you want. Yes, the t-shirt/blazer look is older than Don Johnson in Miami Vice. But notice the 21st-century improvements: slim-fit jacket, rad watch, and badass black color scheme from moody-sensitive-guy tip to sleeked-out shiny leather toe. It’s enough to break down even the coolest high-end art snob and turn her gaze from the art on the wall to the art that you’ve assembled for this getup.  

 Mens date night outfit ideas - Jasper Holland Co

But art galleries aren’t the only date destination where moody black is appropriate. Here are three more casual first date ideas where you can totally rock this look and feel like you aced the scene:

  1. The Dine-to-Impress Upscale Dinner. If your game is impressing people by nature of restaurant choices, this works. That’s because there’s a pretty good chance you’ll be meeting your date at a place that requires you to wear a suit jacket. This look qualifies for all the swankier establishments on your go-to list. At the same time, it doesn’t give off that “just-came-from-the-office” look (which, by the way, you want to avoid at all costs).  
  2. Theatre. Speaking of shows, going to see a play can definitely give you both a lot to talk about and the all-black look is appropriate — after all, didn’t the theatre crowd invent the look? You’ll fit right in. And the benefit of a theatre date is that afterward, you can hit a cafe and bam you’re perfectly suited for the late-night cafe scene as well, you dark & moody person, you.

One last thing. There’s one essential no-no when you’re sporting the blazer/t-shirt look that we must warn you about. This one tiny detail can totally ruin the vibe and which instantly pegs you as a poser. If the collar of your t-shirt isn’t immaculately smooth and sharp, if it’s at all tattered or stretched out, it completely transforms the entire effect.

Instead of dark/moody/cool/cultured, the vibe you’re giving is more like sloppy, afterthought, thrown-together. Just be sure the t-shirt is a good quality one that can hang with the toniest of blazers.

Good Luck Out There

So that’s two-dozen ideas for what to wear on a casual first date for men. Somewhere in all that, there’s a look that you can sport without feeling like you’re pretending to be someone else (even if you are…).

The best advice here is not to make things too complicated because you’ll just end up causing yourself (and possibly your date) a whole lot of unwanted stress.

Whether you choose to go the traditional route and meet for dinner for your first date or you end up doing something kookier like taking a cooking class together (cringe), at least you know you’ll look good doing it.

And then your only problem will become what to wear on the second date. But don't worry, we just gave you a ton of options. 

1 comment

  • As a lady, I especially dig #2 and #8. I like to feel like a guy actually tried when he put his outfit together, mostly because it feels like that expectation can be a little one sided at times. (How many times have I spent tons of effort looking nice only for a guy to show up in a t-shirt and jeans?)

    That isn’t to say that guys can’t dress casual, but it’s nice to see some effort being put in here. (Also, a cooking class is so not cringe, it’s sweet, and anyone who says otherwise can fight me, lol.)

    Emily Pritchard

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