Fellas, we know it can be tough out there on the dating scene.
The main thing you’re usually worried about is whether or not you and your date are vibing together. Are your jokes landing? You hope so. A couple of twenty-two dollar cocktails in, and suddenly you’re worrying about the bill. You look down at your outfit, then glance across the table, followed by a quick survey of surrounding couples.
Did I even dress right? You ask yourself.
That last part can sometimes be one of the trickiest components to a date gone well. Because truth be told, clothing choice matters. First impressions matter. Even if you’re in an established relationship, choosing the right outfit for date night can be the difference between showing you care and showing you’d rather be elsewhere.
The right outfit tells your date that you put thought into things, and it communicates your overall sense of awareness. Which is all rather important, if you ask us.
Determining the right outfit choice becomes increasingly more complicated once you consider the many types of dates you can go on. From first forays to ten-year anniversaries, from bowling alleys to the nicest cocktail lounge in town – each setting and occasion may call for something different. What’s a guy to do? Not to worry.
We’ve prepared a helpful guide to choosing better date outfits, so that next time you’re getting ready, you can refer to this page as your personal stylist.
Casual First Dates Call for Elevated Casual Outfits
Ninety-percent of the time, first dates are not meant to be complicated affairs. In today’s dating culture, some of the most common, typical first dates involve meeting each other for coffee or grabbing some light drinks at a local bar. Nothing too fancy.
While you don’t need us to tell you not to wear a top hat and tailcoat, you might be wondering how to stand out and put your best self forward when the occasion’s dress code still lands on the fairly casual side.
Meeting someone for coffee should not require any overthinking, but here are a few suggestions.
Stick with jeans or chinos that fit you well.
That means no awkward bunching or pulling from being too tight, nor pooling around your ankles as a result of being too large. Straight-fit pants and jeans tend to be the most universally flattering.
Looking for more texture? In cooler months, swap your chinos for corduroy trousers to make your outfit more visually interesting, but still rooted in a casual foundation.
If it’s on the warmer side, pair it with a simple, tasteful t-shirt. Graphic tees are acceptable if the design is either small or minimalist. But you don’t want it to be too loud. Keep the gag tees at home, fellas.
Unless it’s absolutely broiling outside, outfits almost always benefit from an additional layer. Try adding a cardigan sweater to the mix to smarten up your casual ensemble.
White sneakers are an easy addition when it comes to footwear, but don’t be afraid to wear something more colorful so long as the scale of your shoes don’t throw off the otherwise neat proportions of the outfit. A casual derby shoe, loafer, or even chukka boots are also excellent choices for footwear.
If the weather permits it, this outfit can be improved and smartened up a drop more by utilizing a piece of textured knitwear as the top layer, and smartened up a tad by swapping out the tee beneath for an oxford shirt.
If it’s really chilly out, make sure your outerwear game is on point, too! While a classic puffer jacket or parka coat is completely acceptable, a peacoat or even an overcoat can make a really strong impression, and is guaranteed to elevate your look. And don’t forget – a nice coat can actually serve as that additional layer we talked about!
Don’t forget to utilize tasteful accessories, too. A simple watch, matching belt, and coordinated jewelry can all take a simple outfit to the next level.
This outfit can work reasonably well in most bar settings, as well. However, not every bar has the same vibe.
Beyond The First Date
As a relationship progresses, you may find yourself frequenting nicer bars and cocktail lounges with your date. These aren’t your typical dives or college beer halls. Every now and then, these spots may have a dress code. No shorts. No ballcaps. You know the type.
However, most of the time, it’s up to you to determine the appropriate attire to match the vibe of the venue. No one wants to feel dramatically underdressed for their date, or compared to other patrons.
The good news is that this isn’t too tricky to get right, either. In many instances, you can get away with the following formula – take one of the outfit combos mentioned in the previous section, and simply add a blazer or a sport coat.
While there’s a lot more to it in order to do this well, the basic principle remains the same. A sport coat feels right at home with most elevated casual looks. Wearing tasteful jeans and a wool sweater? Throw a blazer over it. Wearing chinos and a chambray shirt? Toss on a sport coat. It can even work over a plain white t-shirt.
With a decent understanding of what qualifies as a blazer or a sport coat, plus some minor fine tuning of various details, you’ll be left with an outfit that works in pretty much any bar with halfway-decent digs.
Need a little more specific instruction? Try this. Pick a pair of trousers with a reasonable amount of structure to the, and pair it with a plain oxford shirt. Next, tuck that shirt in. No need to look sloppy. Pull on some loafers and a matching leather belt. Great! You can wear this to the coffee shop right after work.
But going somewhere a bit bougier? A navy blazer adds just the right amount of sophistication, plus it’s super versatile. Look for versions that feature gold buttons to lean into the preppy origins of the garment. It’s more fun that way, if you ask us.
A Couple Of Curveballs
Okay, so by now we’ve outlined a few basic outfit formulas to serve you for first dates, anniversary dinners, and everywhere in between.
Even at the most casual, you’re not gonna end up looking like a slob. These are all very classic, contemporary uniforms.
Executed well, they can look rather exceptional, but there are technically more options available to you, depending on the circumstances.
What Do I Wear If It’s Really, Really Hot Out?
We talked about layering and how it’s basically an outfit cheat code. Your look is guaranteed to be more interesting if you’ve got a nice sweater or jacket on top.
But fellas, we know that sometimes, it’s just too darn hot out to go that route. You still don’t want to look underdressed or boring – so what do you do?
If the setting is still on the casual side, we recommend the ribbed tank + camp collar shirt combo. It’s a classic summer style hack that allows you to keep a multi-layered look on top without sacrificing practicality.
Be sure to tuck the tank top into your pants or shorts, and feel free to wear the camp collar shirt either fully open or with a handful of buttons undone. Throw on some certifiably cool shades, a chain necklace, and you’re golden.
You Mentioned Sport Coats, So Can I Wear a Suit?
Totally! But be mindful of setting and occasion, as always. For more casual dates, such as a sidewalk Sunday brunch, museum visit, or just a coffee run, you might want to avoid full business or wedding attire. Not all suits are formal!
A casual suit, such as one made from a casual fabric like cotton, corduroy, linen, or tweed, can easily be paired with a simple oxford shirt or sometimes even a t-shirt. Keep the details laid back, and you’ll look sharp and put-together, without coming off as too terribly try-hard.
That said, more formal suits have their place in the dating scene. At some of the nicest restaurants or cocktail lounges, you absolutely can wear a fine suit – and even a tie, if you’re so inclined. This is especially appropriate for important occasions, such as your partner’s birthday dinner, or an anniversary celebration.
The Date? Saved.
We hope you found this guide helpful! While there are a wide variety of outfits one can wear on a date, this serves as a blueprint to turn to when in doubt.
When it comes to dating, it’s important to show respect and put your best self forward. Sometimes, a classic, timeless outfit is just what you need to get up and going.
As your style journey evolves, you may feel inclined to experiment more and try out new things. But if you ever start feeling stuck while getting ready to meet someone for that first coffee, don’t forget the basics. They’ll always have your back.