Men’s Underwear Styles
and The Best Types for Every Occasion

Back in the day, men had two choices of underwear: boxers or briefs. Now, there are many styles of men’s underwear for all kinds of pants and occasions. But what’s the difference between briefs and boxer briefs? Or boxers and trunks? What’s the best underwear to wear with jeans, work pants or workout gear? You’ll find the answers (and some new favorite styles) in this ultimate guide to men’s underwear.

We started by asking what’s the most comfortable kind of men’s underwear. Comfort means the best-fitting underwear as well as what gives you the best performance, whether you’re sealing the deal at the office, reaching a personal best at the gym or settling in for some binge-watching. Next, we looked at what styles of men’s underwear are right for different kinds of pants, including jeans, dress pants, workout gear, casual pants and more. With our comprehensive men’s underwear style guide, you’ll be outfitted for any occasion or style of men’s apparel.

• Boxers

  Polo Ralph Lauren Classic Fit Cottom 3-Pack

  When you need to feel natural, you can’t beat boxers—the classic men’s underwear. They give you freedom and breathability, as well as a retro-macho look and feel. Boxer shorts come in prints and colors that let you show off your personal style, even when they’re not showing. The biggest advantage of boxers is comfort, and they now come in a variety of fabrics for different types of fit, from stretchy to all-out roomy.

  
  

  Wear with: Boxers work best under suit pants that have leg room; khakis; and regular-fit jeans. On their own, they can also double as loungewear or sleepwear.




• Briefs

  Calvin Klein Cotton Brief 4-Pack

  If underwear could be your buddy, briefs would be your wingman: They’re comfy to be with, they won’t leave you hanging and they’re good to go for any outing.

  
  

  Briefs give you a snug, comfortable fit, and have the ability to slide into narrow-leg jeans without bunching or showing underwear lines. When it comes to body confidence, briefs give you that full look and feel.

  
  

  Wear with: Skinny jeans and fitted trousers. Briefs are also great under board shorts and other loose-fitting athletic gear to help you keep it all together.




• Boxer Briefs

  Emporio Armani Pure Cotton Boxer Brief 3-Pack

  One of the most versatile styles of men’s underwear. On the practical side, the extra leg coverage of boxer briefs helps protect your skin from chafing when you’re on the move. On the comfort side, their body-hugging fit provides good support. And on the confidence side, their sporty-sexy look has universal appeal.

  
  

  Wear with: Loose-fitting casual pants, like khakis; workout pants or shorts; straight-leg jeans; cool-weather dress pants (such as wool or similar heavy fabrics) to keep potentially itchy fabric away from your skin; and just lounging around.




• Trunks

  Tommy Hilfiger Cotton Classics Trunk 3-Pack

  An update on boxer briefs, trunks give you the breathability of boxers with the fit of a brief. They have a shorter-cut leg than boxer briefs, and a slightly roomier feeling than traditional briefs. Basically, they could become your new favorite underwear style.

  
  

  Wear with: Almost anything, with the possible exception of super narrow-leg jeans.




• Low-Rise Briefs

  Hanro Cotton Sporty Bikini Brief

  What are the advantages of low-rise briefs? Lots: With a cut and fit like a second skin, they offer a snug fit and next to no lines under low-rise and snug jeans, or any other pants you want to wear. They give you a barely-there feeling yet, due to the way they’re constructed, they offer a lot of enhancement. Simply put, low-rise briefs are great for showing off.

  
  

  Wear with: Low-rise jeans or other short-waisted pants; whatever you wear on a night out.




• Compression Shorts

  2(x)ist Firm Control Shaping Boxer Brief

  Compression shorts act like regular underwear but have special extras for the ultimate fit flattery, like waistbands that smooth out love handles and improve posture, back and tummy support, rear lift, pouch enhancement and more to make you look and feel your best. They come in a variety of styles and support levels, in fabrics that keep you comfortable, confident and looking good.

  
  

  Wear with: Any style of pants or workout gear, whenever you need a body boost.




• Activewear

  Saxx Quest 2.0 Performance Boxer Brief

  The best underwear for your workouts gives you support, comfort, freedom of movement and breathability in high-performance fabrics. Men’s activewear comes in different silhouettes, from wide-coverage trunks to barely-there jock straps. They’re all designed to reduce chafing, prevent friction, wick away moisture and dry quickly while keeping you comfortably supported. No matter what kind of sport you do, there’s a style of high-performance activewear for you.

  
  

  Wear with: Workout shorts, gym pants, sweatpants, swim trunks, board shorts, tennis gear, golf pants, racquetball shorts, basketball shorts or your uniform of choice.

When you’re shopping for the best men’s underwear, now you’re an expert! Whatever you’re doing or wearing, you can find the ideal underwear that will not only make you feel comfortable and confident but have you looking and feeling at the top of your game.