6 Underwear Looks For Date Night

Date Night

Whenever you’re getting ready for a date night, you think about what you’re going to wear. And just like any other outfit, you start with your underwear. But who hasn’t gone on a first date where you wished you were comfortably at ease? Or maybe a sixth date when you are anything but at ease, because your date has been getting handsy all night?

Now some people, when they start dating someone, aren’t sure when things should get sexual. We aren’t hear to tell you when its appropriate, and we certainly aren’t here to judge. But we are here to provide underwear expertise. This is our list of underwear looks for date night, starting things slow and ending with a bang.

1. First Date – aussieBum Freedom Boxer


Don’t be a horn dog and don’t be a prude. It is your first date and you’re making a first impression. Keep it classy with the aussieBum Freedom Boxer. The sleek shorts are made from micromodal so you can feel comfortable, and hopefully curb any nerves. The look is sophisticated with the button fly and cut in a masculine. Chances are your date won’t see your underwear right off the bat, but if they do, this is a good first underwear impression.

2. Second Date – Teamm8 Touchdown Brief


Date number two, that means something must be going well. Keep up the good work with the Teamm8 Touchdown Brief. The look is bright and fun without being audaciously sexy. The sporty flair of the brief is attractive, and if these bad boys are spotted peeking out from behind your pants, your date is sure to approve. Although they may not be comfortable enough to tell you just yet.

3. Third Date – PUMP! Raver Brief


You’re getting a little bolder by date three and your underwear should follow suit. The PUMP! Raver Brief is super cute, and if he or she notices the waistband, they’ll know something adorable is happening under your pants. The brief has bright color blocking with blue and green, and is made from a micromesh that is flirty for them and breathable for you.

4. Fourth Date – Mosmann Reuben Boxer Brief


It’s the fourth date and you’re going somewhere a little more formal — an art gallery opening, or maybe a dive bar with better lighting and cloth napkins. The Mosmann Reuben, in the boxer brief cut, is classy with its black body and white polka dots. And the look is made from 95% modal for a luxuriously comfortable fit that will feel great under dress pants or jeans.

5. Fifth Date – Good Devil Rotica Sheer Cheeky Brief


Nowadays, you have it in the bag by date number five. And even if you don’t, there is no harm in having a sexy secret on your mind with every step. The Good Devil Rotica Sheer Cheeky Brief is sheer everywhere except the pouch. The red look in particular is hot, with a bright red band going around the legs. The same red is used for the Good Devil name on the waistband.

6. Sixth Date – Andrew Christian Teaser Jock w/ Show-It Tech


Honestly, any Andrew Christian jockstrap is a safe bet when you think you’re gonna get lucky, or know you are. The Andrew Christian Teaser Jock has neon accents that will glow in the black light of a club, and a sexy V-shaped ‘teaser window’ in the front. The cup also makes your package look bigger, so there’s that too. Maybe your sixth date won’t have shirtless guys recording you as you make out, but maybe it will.

Do you have any lucky pairs of underwear that you reserve for special date nights? Do you think our date night plans take things too slow or too fast? Let us know in the comments below, or by tweeting us @underwearexpert.

For more information on these brands: Andrew Christian, aussieBum, Good Devil, Mosmann, PUMP!, Teamm8

Photo Credit: Andrew Christian, aussieBum, Good Devil, Mosmann, PUMP!, Teamm8