September 16, 2015

Dress to Impress: What to Wear on a First Date

Foolproof outfit tips to help you make a great first impression.

It doesn’t matter how many dates you’ve been on, first dates are always intimidating. Beyond having to think of where to go or what to do, you have to remember to get your hair cut, trim your nails and make sure your pearly whites are both pearly and white. On top of all of this is the age-old question: What do I wear?

You know she’s going to, so be sure to dress to impress.

A first date is the textbook first impression—and you don’t get a second chance at that. You want to make sure you look great without going over the top, all while making sure you’re memorable. Whoever said dating was easy?

Before mentioning what you could wear, it’s important to think about the nature of your date. Where are you going? What will you be doing? What time of year is it? All of these considerations play a factor. To help, we’ve rounded up a few common first date scenarios and our outfit recommendations for each to help you look your best and seal the deal on that second date.

The Coffee Shop Date

Probably the most casual of all first date situations, the coffee shop date is one where you want to look good but not overdone. The best approach for this kind of date is to keep it simple and casual. Your best bet is a slim-fitting shirt with the sleeves rolled up paired with no-fail dark wash denim and simple leather kicks. It’s such an easy-to-wear outfit you’ll be comfortable enough to forget your outfit and focus on what’s important, getting to know your date.

Be ready for anything.

The Activity Date

Whether your date takes place at a salsa dance class or a concert in the park, the most important thing is to be dressed comfortably—which, careful now, doesn’t mean shabbily. Start with a patterned cotton shirt and throw a corduroy blazer or simple cardigan on top for warmth if it’s a cool evening. Pull on a fitted (but not skinny) pair of indigo wash denim, lace up a pair of clean and casual court shoes, and you’ll be ready for anything.

The Casual Dinner Date

Dates of this kind still fall on the on the casual side of the spectrum, so your outfit should reflect the setting. Blazers are great for casual dates because they aren’t too formal and they show that you’ve put some thought into your appearance. Pair a well-fitted blazer with a crisp button-down shirt and tan cropped khakis. Cap off the look with a pair of leather brogues.

The formal dinner date option—you can’t go wrong in a tailored suit.

The Formal Dinner Date

This is an opportunity to look your best, so you’re going to have to break out your best suit. It doesn’t have to be a fancy tuxedo, but a suit that fits you in all the right places and will boost  your confidence. Go for something different and try a colored suit in an indigo or an unexpected dark green. Add a skinny tie and a pair of polished leather dress shoes to complete your dinner date look.

No matter the occasion, make sure your footwear lives up to the rest of your outfit and is suitable for the date’s setting. It has been said that the tell-tale sign of someone with style is what they wear on their feet—shoes are one of the first places your date will look. Last but not least, dab on your favorite cologne (be careful not to overdo it), run a comb through your hair and pop a mint in your mouth before you head out.

Now that you’re armed with a wealth of knowledge pertaining to first-date outfits, it’s time for the actual date. Open the door for your date, ask questions and listen attentively (this means putting your phone away), take a few deep breaths and smile. With your winning personality and your put-together outfit, there’s no reason you won’t get a second date.


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