Let’s be honest—most men don’t replace their underwear nearly as often as they should. Whether it’s out of habit, sheer laziness, or the belief that “no one sees them anyway,” far too many guys are still wearing underwear that has lost its shape, softness, and, frankly, dignity. But here’s the truth: investing in men’s underwear that feels good, looks good, and provides proper support isn’t just about vanity. It’s about comfort, hygiene, and confidence.
Consider this: underwear is the first thing you put on each morning and the last thing you take off at night. It’s the foundation of your outfit, the unsung hero beneath your clothes. And yet, so many men overlook it until it’s too late. If it’s sagging, faded, or otherwise past its prime, it’s a clear sign that it’s time to level up.
The good news? There has never been a better time to upgrade. Today’s market offers everything from breathable cotton boxer briefs to silky boxer shorts and high-performance gym-ready options. Men’s underwear has evolved far beyond the basics, blending style, comfort, and function in ways that make every day feel just a little bit better. After all, starting your day in underwear that actually fits well and feels good sets the tone for everything that follows.
Here are some of the best men’s underwear available right now—tested, trusted, and designed to keep you comfortable…
#1. Best Boxer Briefs Overall: Skims Cotton Boxer Briefs
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It used to raise eyebrows when Skims came up in a men’s underwear conversation, but those days are gone. Since launching its men’s line in 2023, Skims has quickly established itself as a standout in comfort, fit, and design. Take their 5” Cotton Boxer Briefs: crafted from a mid-weight cotton blend, they deliver softness, stretch, and breathability all in one.
What sets Skims apart among men’s underwear brands is its meticulous attention to fit and minimalist design. The waistband sits comfortably without digging in, the fabric feels luxurious against the skin, and moisture-wicking properties keep you fresh during long wear. For those seeking something lighter, the Sport Brief offers the same supportive cut in a four-way stretch, highly breathable fabric—perfect for everything from daily wear to workouts.
#2. Best Boxer Briefs to Buy in Bulk: Calvin Klein Cotton Stretch Briefs
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No conversation about men’s underwear is complete without Calvin Klein. Since redefining the category in the 1980s, the brand has remained synonymous with timeless comfort and elevated style. Their Cotton Stretch Briefs carry that legacy forward—soft, durable, and engineered to provide support exactly where it matters.
These briefs are perfect for men seeking reliable comfort without compromising on style. The contoured pouch delivers structured support, the waistband stays securely in place, and the cotton-stretch blend ensures breathability throughout the day. Decades after their debut, Calvin Klein boxer briefs continue to stand out as one of the best values in men’s underwear, combining classic design with modern performance.
#3. Best Budget Boxer Briefs: Uniqlo AIRism Boxer Briefs
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Uniqlo’s AIRism line proves that high-quality men’s underwear doesn’t have to come with a premium price tag. Known for its lightweight, moisture-wicking technology, these boxer briefs strike the perfect balance between comfort and practicality. They are breathable, quick-drying, and equally suited for everyday wear or intense workouts.
Although they aren’t the most structured or tailored option, the smooth AIRism fabric feels surprisingly luxurious given the price point. They perform effortlessly under jeans, trousers, or gym shorts, making them one of the best-value choices for men seeking reliable performance and comfort without splurging.
#4. Best Boxer Shorts Overall: Sunspel Classic Boxer Shorts
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For traditionalists who favor classic boxer shorts, Sunspel sets the gold standard. This British heritage brand has been refining men’s underwear for decades, and its Classic Boxer Shorts are a testament to that craftsmanship. Made from fine long-staple cotton, they feel silky-soft, drape effortlessly, and are built to last.
What sets Sunspel apart is the thoughtful design, including a shaped back panel that ensures a superior fit with zero bunching—something most cheaper boxers struggle to achieve. These shorts seamlessly blend old-school refinement with modern comfort, making them the ideal choice for men who value elegance even beneath their everyday attire.
#5. Best Budget Boxer Shorts: Uniqlo Woven Trunks
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Uniqlo continues to impress with its woven trunks—a practical, affordable option for men seeking breathable, easy-fitting underwear without breaking the bank. The soft cotton fabric feels gentle against the skin, the waistband offers comfort without digging in, and the roomy fit makes them perfect for lounging or sleeping.
While they may not boast the tailored precision of higher-end boxers, their dependable comfort and consistent quality make them an excellent everyday choice. For men looking to stock up on reliable underwear without compromising on feel or functionality, Uniqlo’s trunks are a standout option.
#6. Best Upgrade Boxer Shorts: Derek Rose Amalfi Boxer Shorts
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For those looking to elevate their men’s underwear game, Derek Rose’s Amalfi Boxer Shorts epitomize luxury. Made from 100% fine cotton that feels as smooth as silk, these boxers blend classic British tailoring with modern refinement.
Subtle details, such as extra buttons, a lustrous sheen, and a carefully calibrated fit, make every pair feel as exquisite as it looks. While they come with a higher price tag, they are an investment piece that redefines how you experience underwear, turning a daily essential into a moment of indulgence.
#7. Best Boxers for the Gym: Lululemon Built to Move Boxer
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Lululemon’s Built to Move Boxer lives up to its name. Engineered for high-intensity activity and all-day comfort, these boxers are the ultimate gym companion. The Luxtreme fabric wicks moisture, prevents chafing, and keeps everything in place even during the most intense sessions.
The fit hugs the body like memory foam—supportive without ever feeling restrictive. While a functional fly would have been a welcome addition, the breathability, odor resistance, and overall performance make these boxers one of the top men’s underwear choices for athletes and active lifestyles.
#8. Best Supportive Boxer Briefs: SAXX Non-Stop Stretch Cotton Boxer Brief
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When it comes to engineered comfort, SAXX has earned a devoted following, and for good reason. The brand’s Non-Stop Stretch Cotton Boxer Briefs feature the signature “BallPark Pouch,” a hammock-like compartment designed to keep everything supported and separated. It might sound like marketing hype, but once you try them, it’s clear this is comfort science that actually works.
These boxer briefs are perfect for men who value support and breathability, especially on warm days or during long hours of activity. The cotton-stretch blend adapts to your shape, while flat seams minimize friction. While some may find the waistband branding a touch bold, the unparalleled fit makes it easy to see why SAXX continues to rank among the best men’s underwear brands for functionality and all-day comfort.
#9. Best Everyday Boxers: J.Crew Patterned Boxers
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J.Crew may be known for its preppy staples, but its approach to men’s underwear is surprisingly elevated. The brand’s Patterned Boxers blend classic American design with modern comfort, striking the perfect balance between tailored fit and ease of movement. A brushed waistband feels gentle against the skin, while the soft cotton fabric ensures all-day smoothness.
These boxers hit the sweet spot between loose and structured—never too baggy, never too tight. The attention to detail is evident: from the charmingly retro button fly to the durable, lightweight cotton that holds up wash after wash. They aren’t flashy, but they deliver where it matters most, making them one of the best men’s underwear choices for those who value timeless simplicity over passing trends.
#10. Best Classic Knit Boxers: Calvin Klein Cotton Classics Knit Boxers
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Calvin Klein doesn’t just dominate the boxer brief category; the brand’s Cotton Classics Knit Boxers prove it excels at traditional boxers as well. Crafted for men who prioritize softness and freedom of movement, these knit boxers perfectly balance comfort, nostalgia, and iconic branding.
Made from pure cotton with just the right amount of structure, they’re ideal for lounging or sleeping. The relaxed cut moves with you without riding up, while the soft elastic waistband keeps everything secure. For longtime fans of Calvin Klein, these boxers are a natural evolution. Indeed, a reminder that men’s underwear can be both timeless and reliably comfortable.
Time to Upgrade What’s Underneath
If your drawer is crowded with faded, stretched-out underwear, it’s time to make a change. Investing in quality men’s underwear isn’t about chasing trends. It’s about prioritizing comfort, support, and confidence from the ground up. Whether you prefer sleek boxer briefs, roomy classic boxers, or performance-driven athletic options, today’s market offers styles that suit every lifestyle.
So, man to man: ditch the worn-out pairs and upgrade to underwear that feels good, fits well, and lasts longer. Your wardrobe, and more importantly, your body, will thank you.
Featured image: @calvinklein/Instagram
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