5 Shirts to Impress a First Date

Let your personality shine through your style with these great date shirts. 


First dates are best described with a venn diagram: On the left, nerves; on the right, hope; and in the middle, either the beginning of a great love story or the most awkward night of your life. To do your part to ensure that it’s the start of something fun, at the very least, dressing the part always helps. Rather than a plain tee, there are tons of different style to consider so you can dress to impress. Here are some of our favorite first date looks on dudes.

BOTVELA Men’s Shawl Collar Cardigan Sweater Button Front Solid Knitwear


If winter has arrived during first date season, you cannot go wrong with a chunky cable knit sweater. Not only will you look really snuggable, you’ll also be cozy and comfy. This knit comes in four colors, so it can be matched with jeans or dressed up for business casual with khaki slacks.

Paul Fredrick Men’s Linen Casual Shirt


Linen shirts always look effortlessly cool, and because the fabric is naturally cooler and more sweat-wicking than cotton, it’s perfect for warm weather. A bold color can be a great way to “peacock” without overdoing it. This salmon pink is the perfect blend of subtle and stylish—plus it looks super comfy.

Acid Rain Tee


If you just can’t fathom wearing anything but a tee shirt, pick one with style. A striped, high-quality tee can look really sexy on a dude who oozes confidence (and pairs them with great jeans and shoes—and maybe a blazer).

Visive Original Printed Short Sleeve Button Down Shirt Size


If you’re more of a laid-back dude, a printed button down is a great way to show off your personality. Choosing a fun print signifies that you have the capability of styling yourself (seriously, a burden that falls far too often on the ladies in a man’s life) and proves you aren’t afraid to keep it at least a little weird.

Hemp LS Henley


Perhaps I’m basic, as the kids say, but there is something incredibly sexy about a dude wearing a henley. I really love how effortlessly this tee hangs and looks on any size or shape dude—it looks dressy without being formal. Perfect boyfriend, er, I mean, first date material.