Change Your Underwear from Boxers to Briefs in 10 Easy Steps


Are you one of those guys who wants to get out of boxers and into briefs? Making the transition from loose-fitting, free-balling styles to cradling briefs and low rise trunks can be daunting, no doubt, but it’s most definitely not impossible.

How do you know you’re ready to make the change, though? If jamming your underwear into fitted, skinny jeans and chinos proves impossible, or if your underwear comes down with your pants at the gym, or if you can’t keep everything in place when you’re out for a jog or at the gym, you’re ready. You’re really ready.

Change your underwear from boxers to briefs in 10 easy steps. If you’ve decided to move from saggy, roomy boxers to the way more pragmatic choice – briefs, trunks or boxers briefs tailored to your body and needs – you’re already on the way!

tumblr_mfey4cVAfX1s18sh3o1_400 (1) 21. Acknowledge the Problem. Most boxers and boxer briefs aren’t meant to be worn with today’s trendy, fitted looks. Besides the wardrobe benefits, a switch to briefs will give you and your boys the support they need and deserve.

2. Don’t Quit Cold Turkey. Changing from boxers to briefs is going to take some time, both for mind and body. Don’t start by tossing your entire underwear drawer in the trash.

3. Look Before Your Buy. When it comes to briefs these days, your options are endless. Spend some time browsing the websites of your favorite brands to see what smaller styles they have available for you, then check out underwear retailers like and International Jock for a more comprehensive assortment.

4. Evaluate Your Budget. Transitioning to quality underwear is a worthwhile investment. There will be some sticker shock at first but it will fade once you pull on that first pair of briefs.

5. Repeat: Quality Above Quantity. Underwear that comes in a pack of ten or more is going to fit and support you like two-dollar underwear should. There is more value in one pair of $24 briefs than there is in 10 boxers for $25. It’s simple guys, you get what you pay for.

6. Make Sure the Size is Right. Buying the right size brief or trunk is critical to how it will fit and function on your body. Your size in most brands will be the same as the size of your best fitting pair of jeans. Pay special attention to each brand’s website’s sizing charts, and keep in mind, a size in one brand won’t necessarily fit the same as a size in another.

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7. Start Small. Buy two or three pairs at a time. It’ll save you money in the near term, allow you some time to know what you like and don’t like about the underwear and it will ease the transition.

8. Start with Big Names. Your first few pairs should be from brands like Calvin Klein, C-in2 and 2(x)ist. Their fit, comfort, and quality are unparalleled; they’re the home-runners in this sartorial category. From each of these or other big brands, start with the most recently released collections and most popular styles.

9. Wear, Learn, and Don’t Give Up. The best thing about the fit of briefs or trunks is that they give your body instant feedback. Pay attention to size, package fit, the seat and fabric. Keep in mind what you don’t and do like, and next purchase, make sure you’re looking for exactly what you need. Eventually, you’ll find a pair or style that’s perfect for you.

10. Become an Underwear Expert. Make sure you’re up to date on the newest rends, releases, reviews and underwear campaigns right here on The Underwear Expert. You’ll thank us in the long-run, and so will your boys.

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Photo Credit: Sean P. Watters