Men’s Underwear Buying Guide: Briefs, Trunks, Boxers, and More

Choosing the right underwear is one of the most overlooked decisions in a man’s wardrobe. The wrong pair can lead to discomfort, bunching, or lack of support, while the right pair can make you feel confident and comfortable all day long. Whether you’re dressing for the office, the gym, or a casual day at home, understanding the differences between briefs, trunks, boxers, and boxer briefs is essential.

In this men’s underwear buying guide, we’ll walk you through each style, its pros and cons, and how to pick the best men’s underwear for your body type and lifestyle. By the end, you’ll know exactly what to look for—and which Tommy John styles deserve a spot in your drawer.

Briefs: Classic Support and Minimal Coverage

Briefs are the original underwear style, offering full support with a snug fit that sits at the natural waist. They feature a Y-shaped fly and leg bands that sit high on the thigh, minimizing fabric and maximizing freedom of movement. For men who prioritize support and a clean silhouette under slim-fit pants, briefs are a top contender.

Modern briefs have evolved far beyond the tighty-whities of the past. Brands now offer performance fabrics, moisture-wicking properties, and no-roll waistbands. Tommy John’s briefs use Second Skin fabric that moves with you, reducing chafing and keeping you cool. If you’re an athlete or someone who hates bunching, briefs might be your new go-to.

• Ideal for athletic activities and everyday wear under fitted trousers
• Provides maximum support and minimal fabric
• Look for moisture-wicking and anti-odor features for all-day comfort

Trunks: The Modern Hybrid

Trunks are a relatively new addition to the underwear scene, combining the short leg of a boxer brief with the snug fit of a brief. They sit lower on the hips and offer a square-cut leg opening that stays put without riding up. Trunks have become wildly popular for their modern aesthetic and versatility.

For men who want the support of a brief but with a bit more coverage, trunks are an excellent choice. They work well under jeans and chinos, thanks to their shorter leg length. Tommy John’s Ultra Soft Flex Trunk 4" (7-Pack) is a customer favorite for its stretchy, breathable fabric and no-roll waistband. It’s a smart investment for building a reliable underwear rotation.

• Great for low-rise pants and modern fits
• Offers a balance of support and coverage
• Look for a 4-inch inseam to prevent riding up

Boxers: Classic Comfort and Breathability

Boxers are the loosest style, offering a relaxed fit with a button or elastic waistband and a longer leg that extends down the thigh. They provide excellent airflow and freedom of movement, making them ideal for lounging or sleeping. However, they can bunch up under tight pants and offer less support than other styles.

If you prioritize breathability and a non-restrictive feel, boxers are a solid choice. Modern boxers often feature performance fabrics that wick moisture and reduce friction. Tommy John’s Second Skin Relaxed Fit Boxer 6" is designed with a soft, stretchy fabric that moves with you, plus a no-roll waistband for all-day comfort. They’re perfect for casual days or as sleepwear.

• Best for loose-fitting pants, lounging, and sleep
• Provides maximum airflow and minimal compression
• Choose a relaxed fit with a supportive waistband to avoid bunching

Boxer Briefs: The All-Rounder

Boxer briefs combine the length of boxers with the snug fit of briefs, offering a versatile option that works for almost any activity. They provide support, coverage, and a secure fit that stays in place. The leg length typically ranges from 3 to 9 inches, with 6-inch inseams being the most popular for everyday wear.

For men who want a single style that does it all, boxer briefs are the answer. They’re ideal for the gym, the office, and everything in between. Tommy John’s Second Skin Mid-Length Boxer Brief 6" (3-Pack) delivers a second-skin feel with moisture-wicking fabric and a no-roll waistband. It’s a staple for anyone building a versatile underwear collection.

• Versatile for daily wear, exercise, and work
• Provides support without sacrificing coverage
• Look for a mid-length inseam (6 inches) for the best balance

How to Choose the Best Men’s Underwear for Your Needs

Now that you know the differences between briefs, trunks, boxers, and boxer briefs, it’s time to consider your personal preferences. Think about your typical activities: Do you need support for the gym? Go with briefs or trunks. Do you prefer a relaxed feel for lounging? Boxers are your friend. For all-day versatility, boxer briefs are hard to beat.

Fabric also matters. Look for moisture-wicking, breathable materials like microfiber, modal, or cotton blends with stretch. Tommy John uses Second Skin fabric that feels weightless and keeps you dry. Also pay attention to the waistband—a no-roll design prevents digging and keeps your underwear in place. Finally, consider pack options like the Ultra Soft Flex Trunk 4" (7-Pack) to stock up on essentials.

• Match the style to your daily activities and wardrobe
• Prioritize fabric technology for comfort and durability
• Invest in multipacks to save money and simplify your drawer

Finding the perfect pair of underwear doesn’t have to be a guessing game. Whether you prefer the support of briefs, the modern cut of trunks, the breathability of boxers, or the versatility of boxer briefs, Tommy John has options designed for all-day comfort. Start your upgrade with the Ultra Soft Flex Trunk 4" (7-Pack) and experience the difference that quality fabric and thoughtful design can make.