After a few weeks of social media following (stalking?), anxiously trying to figure out the right thing to say without seeming desperate, you’ve now secured a date. Great work. So you’ve got the dinner reservation set up or low-key cocktail bar on deck, now it’s time to consider what you’re going to wear. Even if you’re coming straight from work and will be dressed up, you should still put some thought into an outfit upgrade. Whether it’s a coffee date, cocktails, brunch or even a dressy evening out, these foolproof looks will have you looking sharp and ensure it’s not your style that doesn’t get you that next date. We can’t say the same for your terrible jokes though...
The Coffee Date
Coffee dates can be dicey in the style department. It’s a possible daytime/afternoon scenario so you want to keep it casual but still look your best (For what it's worth the midweek daytime coffee date is not a date, you're better than that. Nobody ever got laid after a midweek coffee date). Flexibility is key too, it could always transition into more plans. Let’s keep it casual and not overthink it. A tee-shirt or casual button-down layered under a zip-up jacket is a great place to start. Finish it with sneakers and a great pair of jeans or chinos. If you’re looking to add a little extra personality, try a pair of colored chinos for some extra vibes. Fit is key here, just because you’re going casual doesn’t mean you shouldn’t be focused on looking put together.
Meeting for a few cocktails after work or on the weekend is a great first date. Nighttime dictates a bit of elevated style, and as we said before, a date deserves something outside of your midweek suit, so consider this a flex zone. This is a great opportunity to work a high/low vibe so try a solid or patterned blazer paired with a t-shirt and a crisp pair of denim. For shoe choices, pair with a clean pair of sneakers or a loafer for a great finish. This look is going to let your date know you took the time to think about the occasion and rock some personal style. The second you show up looking this good you’re already going to be ahead of the last loser she met on Hinge.
A good brunch can be the start of a great relationship. There’s something about a good Saturday night recovery meal and drinks (Sunday Funday, boo-ya). Meaningful conversations can even turn into a day of drinking that will have you jumping around the city well into the evening. Sundays are for relaxing, so even if you’re not entirely sure what may take place after brunch, keep your style pretty chill. To strike that perfect balance between stylish and laid back, try a cool print shirt paired with your favorite pair of denim. It’s going to read casual but not “I woke up like this.” Pull it all together with a club or varsity jacket and a pair of sneakers.
A Classy Dinner
So you’re really pulling out all the big guns for this date. Respect. We’re certain your lady will appreciate the extra effort. For a date like this, it’s time to pull out the sartorial big guns as well. You want to dress it up but you also don’t want to seem like you’re trying too hard; it’s a fine line but we’re here to help you navigate. The perfect mix is dressing up chinos with a blazer and a tie. The blazer screams “style” and a tie will let ‘em know you’ve got the confidence to wear one because you want to, not because you have to. Finish your look with a slick pair of loafers of a pair of double monks and you’re on your way to success.
For a quick-change guide at the office, check out our Dress Smarter video.
Looking for a few date ideas? Check out our handy guide to nailing dates 1 through 3.
Good luck out there!