First dates can be tricky because, well, it basically makes or breaks your chances of moving forward with that cute new girl. But as long as you avoid saying these things, and start the conversation with these things, then we'll help you nail the other important part of a first date: your attire. Because, while much of what you say is important, your appearance is key to impressing her long before you even speak.
First dates typically happen in one of three settings: a daytime environment (like a casual coffee), an evening scene (like a formal dinner), or a late-night setting (like drinks at a bar). So, we pulled together three looks to wear on each occasion. But, this guide goes a step beyond the traditional “safe” looks that you’ll see on any occasion. Here, we found the most stylish yet still approachable pieces you’ll need to seriously impress her.
You can count on the following three outfits to land you that second date—and more.
This top from Saturdays NYC is light enough to wear as a shirt and thick enough to transition into a jacket, which will come in handy when your day-date turns into something unplanned. Not only is the material right for the environment, the silhouette is relaxed, the camel color is cozy, and the deep brown button details and chest pockets make it undeniably masculine.
If you want to keep things casual yet still deliver an air of confidence, rock these AG Jeans on your bottom half. Their clean lines and dark shade will look fresh and, once you see the next slide of stylish soles, are key to smoothly bringing your look together.
Ditch the ordinary low-tops and make a power move with these high-tops from Coach. The light saddle shade against the dark black provides a striking contrast, the fine construction instantly elevates the look, and the silhouette delivers a hit of contemporary cool, which is exactly what it takes to bring your outfit to the next level.
Keep things appropriately dressed down with this sleek leather watch by Skagen. The slim style isn't too overbearing, the black color compliments the rest of the look, and the silver details keep the ensemble fresh and modern.
You can’t go wrong with a button-front style for a late-night ambiance, but your choice of shirt says everything. Go with this top from Thom Browne to impress your date. Not only will it grab her attention, its will set you apart from everyone else in the room. Thom Browne's signature stripe, which, in this piece is across one sleeve, is sporty and sharp while still being subtle—so it will make a bold statement without being obnoxious. It may be on the pricier side, but its quality construction and exquisite design makes it well worth the investment. (If you don't have the budget, we've got 12 more great options here.)
Jeans are easygoing, 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. The stretchy material will ensure comfort, the minimal design isn't too flashy, and their selvage trim is an instant upgrade from your average pair.
If you want to attract her attention in a crowd of people, break out a pair of kickass boots like these from Frye. The classic tailoring topped with the brogue design delivers the ultimate combination of refined and rugged. And their unparalleled quality means they’re built for a lifetime of wear.
This watch by itself is a conversation starter. The brown leather band coupled with the black dial is daring, while the stainless steel case with a coin edge finish keeps it polished. It's the perfect accessory to complete your late-night ensemble.
Anyone could go with a traditional dark navy blazer, but it you want to go the extra mile, throw on an unexpected hue like this light blue blazer from J.Hilburn. It will convey elegance and masculinity, which is exactly what you want in this type of ambiance. (If you're looking for a lower-priced option, click the link below.)
Wearing a t-shirt underneath a jacket is too summer-esque, and can look a little too understated. Master the look from head-to-toe by putting this crisp white dress shirt underneath your blazer. She’ll appreciate the classic style and it will make you look sophisticated, too.
Trousers can go a long way, especially if you snag this pair from Suit Supply. The tailored slim fit is flattering, the cotton material will ensure they’ll remain comfortable, and the tapered flat front leg dresses it up a notch.
Women take note of the soles on your feet. Not just the style, but the quality and condition, too. Skip the laces and go for a monk strap style like these from To Boot. The aesthetic is understated yet smart—an approachable combination that's perfect for a formal setting. Plus, its fine construction and timeless cognac color will last you years.