Aside from verbally saying the right things (see: 50 First Date Conversation Starters), what you wear is key to making a great first impression and, ultimately, landing that second date.
Kicking things off in a less formal setting means you're in luck (no stiff suits for you!). But while it may be in a casual environment, this isn't a hall pass for wearing joggers and a t-shirt. It's about looking pulled together in a head-to-toe ensemble that exudes an air of confidence, but with a cool, calm, and collected vibe. And it's also important to feel comfortable with what you're wearing while conversing with your date from across the table, too.
Sounds like a lot? Don't sweat it, here we've listed 10 essentials—from your hair to your shoes and everything in between—to seriously impress your date.
Just make sure you steer clear of the 5 things to never say on a first date in the link below.
Wearing a t-shirt can look messy, and in this case, a little too understated. Remember: you’re trying to make a make a great first impression, not have her run for the hills. Stick with a traditional button-up shirt like the one pictured above from Untuckit. The style is a classic, the crisp white hue with a subtle pop of navy at the collar is sharp, and it's designed to fall at a length that can be "untucked" (hence the name) so it's ultra comfortable, too. Plus, you won’t have to worry about showing up in matching flannels.
Nix the cotton cardigan and stiff blazer. Instead, take advantage of this casual ambiance and make a power move with a cool bomber jacket that serves as a sporty layer. Try this fine navy option from Club Monaco—it will convey elegance and masculinity, which is exactly what you want. And if you ask us, a bomber beats the look of a cardigan.
Trousers are too much, khakis feel like you’re in the office, but jeans? They’re relaxed, comfortable, and even deliver a bit of sex appeal, too. Just make sure to invest in a solid, dark denim pair with a slim fit like this sharp pair from Nudie. Its stretchy material will ensure comfort, the minimal design isn't too flashy, and their selvage trim is an instant upgrade from your average pair.
Sneakers may be your favorite staple in your wardrobe—and they may even look acceptable in most casual settings—but women take note of the soles on your feet. Not just the style, but the quality and condition, too. Go with these Chukka boots from J.Crew to complete your ensemble. The style is more posh than kicks but less stiff and formal than dress shoes so it makes for the perfect middleground.
A sleek watch has the power to instantly and effortlessly enhance your entire look. Picking the right one is crucial, though, and a man should definitely invest in a great timepiece. So make sure your wrist is equipped with a classic, stainless steel model like this one from Tissot. Its steel band coupled with the navy dial is timeless, masculine, and will show that you have great taste. Plus, it also shows that you're attentitive of time.
The last thing you want to do is graciously pick up the tab—only to kill the mood by whipping out a beaten up velcro wallet. Trust us: she'll notice the little things. Get your hands on this Jack Spade bifold for the big evening—it's spacious, sturdy, and will last for years thanks to its timeless aesthetic.
They may be hidden, but sure enough, your jean hem will rise and your date will notice if you’re wearing a stained, white, loose-fitting crew pair that looks ten years old. Needless to say, don’t overlook your socks. This navy pair from Mack Weldon adds just the right amount of flair and has the benefit of keeping your feet odor-free thanks to its infused silver technology that wicks stench.
Getting a whiff of the perfect scent can make some women weak in the knees. (Just make sure to read our guide on how to apply cologne without overing doing it.) You can't go wrong with this bottle by Givenchy—it has a warm sandalwood and vanilla spice aroma that will make any girl swoon. Afterall, scent is the strongest sense attached to memory.
Let's face it, nobody wants to be the guy with massive pit stains on their shirt during a first date. Not only does wearing deodorant make you seem more masculine to women, per this study, but maintaining great hygiene should be important at all times. Spray yourself with this option from Dove Men + Care before you walk out the door. It's unscented (so it won't clash with the scent of cologne), and has both deodorant and antiperspirant properties so not only will you stay dry, but you'll keep bad body odor at bay, too.
Dove Men+Care Dry Spray Antiperspirant $5.22, amazon.com
Showing up to a first date with messy hair just looks, well, messy. You want to at least look like you put effort into your grooming routine to impress your date—it just shows that you care. Just don't hit up your barber the night before to pencil you in for a new style you've been itching to try. You're better off working with what you're used to before a first date. When it comes time for the big evening, we have everything you need to know in this guide on the best classic hairstyles for men.