What Makes Great Date night pair of Underwear? One that will be remembered for future dates? We have a few suggestions on that. But the underwear depends on which date it is (first, thrid, or fifth) and the connection you have to the other person on the date with you.

Over the course of the blog fewer things have brought controversy like bringing up date night underwear. That is because to each guy “Date night underwear” means something different. Underwear is personal and date night underwear is even more so!

We decided to break down a few categories of date night underwear and have you guys tell us which pair you wear and why?


Classic Underwear – We don’t mean the tighy whities that come in a six pack. Rather a brief/boxer brief that is no frills. It’s styling is simple but very comfortable.  One pair that would be good is the 2(X)ist Essential No-Show Brief or Trunk. Another pair is the Calvin Klein Bold Cotton Boxer simple with an off setting waistband.

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Colorful/Patterned – Colors are an expression of our personalities. On a date night there is a greater chance the underwear will be seen. I know in the past I have worn really fun/bright underwear when there is a chance things get busy. A great pair of colorful underwear is JOR Paris Brief. If you’re a boxer brief fan then you should look into the Papi Eye Candy Brazilian trunk.

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Jockstraps/Jockbrief – Many of our readers wear jocks every day. They are no longer just for the locker room. Over the last few years companies have been putting their own spin on the jock. The C-IN2 Grip jock is the perfect example of a company taking the jock to the next level. If you’re not up to wearing a jock but want the coverage of a jock, the orignator of the  jock brief Baskit has the Pure Jockbrief.

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Erotic/Mesh – If you’re past the first date or out with your significant other maybe you want to show a bit more of your wild side. This could be either Mesh or something considered wild. If you want to show off everything with mesh then we suggest the Gregg Homme NoDoubt Thong Maximizer, It shows and enhances. If you don’t want to share it all but want to wear something you won’t find in your local department store, then we suggest Modus Vivendi 11011 Leather Look Brief with Zipper.

These are some examples of different types of underwear you can wear on a date night. You can go from mild to wild depending on the date! Let us know what pair you like to wear on your date.


Tim is the founder and editor of Underwear News Briefs. He has been an avid underwear fan since the age of 14! He founded UNB in 2008 and has continued to broaden his underwear love over the years

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