Regular readers of this site know the importance and benefits of wearing great looking underwear. The confidence boost, sex appeal and overall feeling it gives you is all the reason you need to ditch the 3-pack of saggy department store boxer briefs. But if you’re new to the wonderful world of underwear, or just want some suggestions on new pairs to wear on a date night or the upcoming Valentine’s Day, we have you covered. I’ll give you some options based on how long you’ve been with a person, and whether your tastes run mild to wild.

First date

If this is your first time out with a guy or girl, or even if you’re out with friends and think that there’s a chance you might be showing someone your underwear, it’s always a good bet to go classy yet sexy. You don’t want to scare someone off if he or she isn’t expecting something like a leather jock on the first night. Therefore, choose something black, simple and sophisticated.


Black trunks in a high-end fabric benefit you and your partner. You get to look, and feel great, plus your partner gets the hint early on that you’re capable of doing better than Hanes from Target. The 2(x)ist Speed Mesh No Show Trunk shows that you care how you look, even if you’re 99% naked. It’ll give you the confidence from the start to make this work! It also sets the stage that your underwear choices will be a step above the normal guy.



Sticking with black but also not going too crazy, black briefs are a classic can’t miss. There will be plenty of opportunities to show your crazy and kinky side; the first date isn’t necessarily one of those times. There is nothing better for this than a Calvin Klein

Steel Micro Hip Brief. It’s an amazing feel and if someone has a problem with you wearing this, they’re not for you. Rock this on the first night and you’ll have no worries about showing them your wild side soon!

A few dates in

By this point, you’re comfortable enough with a person where they should know the type of underwear you prefer. You and your partner might be to the point of getting down to your underwear when you’re sober or in daylight!


Even if you lean towards the mild side, you can still show some thought and effort to all aspects of your outfit. You had a solid start with sleek and sophisticated black, so now you can start showing your creative side with some color in your underwear. The Pump Frosh Jogger gives you a solid burst of color in a cut that shows you off in the best ways. It’s cut small enough to make your date very happy to see you in them, but still mainstream that you can wear them in the gym without raising any eyebrows.



At this point in a relationship, someone with a taste for the wilder side of underwear can start breaking out the fun stuff! Anything from Gregg Homme will make you look and feel like a rockstar. The Torridz Hyperstretch low-cut brief has an amazing 8-way stretch material that will do wonders to highlight your best assets. Pick a great color like aqua and your partner will be constantly trying to get a peek in your pants to see if you’re wearing this super sexy pair.

A special night

After you’ve been with someone for a while, you might want to plan a special evening or even just want to spice things up a little. This calls for some kickass undies! Even if you think you lean towards the mild side, break out something like the pairs below to really impress your partner.


Whether or not you call yourself mild when it comes to underwear, you owe it to yourself and your partner to strut your stuff in a thong every once in a while. There are too many great looking and fantastic fitting thongs made for men these days to miss out. Picking the Sports Thong from Cocksox is the best way to bring out the big guns yet still feel fairly mainstream. This pair has a near perfect cut and fabric, so pair a special night with a special pair. You (and your partner) will not be disappointed.


If you think of underwear as the ultimate form of expression and have no issue wearing anything and everything, picking out something wild for a special night opens all kinds of possibilities. This is where you can incorporate great cuts with wild fabrics. The Modus Vivendi Flash Floral Lace Jock delivers all that and more. You get the super minimal jockstrap cut that shows off everything about you, plus the awesome look and feel of that great blue and red lace. Maybe this is the first time your partner has seen something this wild from you, or maybe you both know that a special night calls for the special undies and hopefully…a special ending! Enjoy!


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