Best Hipster Underwear Trunks for Men of 2026

John Zimmer Avatar
John Zimmer
Last Updated: 3 Feb 2026

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Introducing a range of stylish and comfortable hipster underwear trunks designed for men. These trendy trunks offer a modern and fashionable alternative to traditional underwear styles. Made from high-quality materials, they provide a snug fit and ultimate comfort throughout the day. With a variety of colours and patterns to choose from, these hipster trunks are perfect for the fashion-conscious man looking to update his underwear collection. Whether you're heading to the office or hitting the gym, these trunks are a must-have addition to any modern man's wardrobe.

At a Glance: Our Top Picks

ANTONIO ROSSI Men's Hipsters Fitted Boxer 12-pack Cover #TOP 1
ANTONIO ROSSI Men's Hipsters Fitted Boxer 12-pack
ftb score rating icon 9.9
INNERSY Men’s Quick Dry Breathable Boxer Shorts 4-Pack Cover #TOP 2
INNERSY Men’s Quick Dry Breathable Boxer Shorts 4-Pack
ftb score rating icon 9.8
INNERSY Classic Cut Men's Boxer Briefs 4 Pack Cover #TOP 3
INNERSY Classic Cut Men's Boxer Briefs 4 Pack
ftb score rating icon 9.6

Top 4 Hipster Underwear Trunks for Men

#TOP 1

ANTONIO ROSSI Men's Hipsters Fitted Boxer 12-pack

AR-HIPSTER-12-DA-L
Dark Assorted
ANTONIO ROSSI Men's Hipsters Fitted Boxer 12-pack Cover
ANTONIO ROSSI Mens (12-pack) Hipsters Fitted Boxer, Dark Assorted, L UK

The ANTONIO ROSSI Hipsters Boxer offers all-day comfort with a luxurious blend of combed cotton that feels soft against your skin. The elasticated waistband sits smoothly at your waist, preventing any digging in. Enjoy lasting freshness thanks to its breathable material, which wicks away moisture to keep you cool. The 4-way stretch provides ergonomic support, ensuring a custom fit that allows for flexible movement, while the contoured front pouch keeps everything securely in place, so you can go about your day with confidence.

What We Like
Comfortable soft touch fabric
Moisture-wicking for freshness
Flexible 4-way stretch
Contoured pouch for support
Minimises riding up
#TOP 2

INNERSY Men’s Quick Dry Breathable Boxer Shorts 4-Pack

INNERSY Men’s Quick Dry Breathable Boxer Shorts 4-Pack Cover
INNERSY Boxer Shorts Men Breathable Trunks Underwear Quick Dry Hipster Underpants Multipack 4 (L, Black/Brown/Wine/Navy)

The INNERSY Boxer Shorts are designed with quick-dry mesh fabric that keeps you cool and comfortable, ideal for daily wear or exercise. Their lightweight and thin material means you can barely feel them under your clothes, perfect for summer. The ergonomic 3D pouch provides excellent support without tightness or bunching, giving you freedom of movement throughout the day. Additionally, the elastic waistband ensures the trunks stay in place without rolling down or digging in, offering a snug and secure fit.

What We Like
Lightweight, breathable fabric
Supportive 3D pouch design
Elastic waistband stays put
No ride up on legs
Tagless for comfort
#TOP 3

INNERSY Classic Cut Men's Boxer Briefs 4 Pack

INNERSY Classic Cut Men's Boxer Briefs 4 Pack Cover
INNERSY Boxer Briefs Mens Underwear Trunks with Fly Cotton Underpants Fitted Hipster 4 Pack (XL, Navy Blue/Grey/Dark Red/Green)

The INNERSY Men's Boxer Briefs offer a comfortable fit for everyday wear with their classic cut and stretchy cotton fabric. The 3D open fly design allows for easy access while enhancing breathability, ensuring you stay fresh and dry throughout the day. Additionally, the elasticised waistband keeps the briefs in place without rolling down or digging into your skin. With soft leg openings that prevent pinching, these boxer briefs provide the support needed for active lifestyles, making them ideal for running or jogging.

What We Like
Comfortable everyday wear
Easy access with open fly
Stay-put waistband design
No ride-up leg openings
Machine washable for convenience
#TOP 4

wirarpa Men's Cotton Stretch Hipster Boxers Pack

1408W-4P-S
White
wirarpa Men's Cotton Stretch Hipster Boxers Pack Cover
wirarpa Men's Hipster Boxer Shorts Cotton Stretch Underwear Trunks for Men Pack of 4 White Small

The wirarpa Hipster Boxers are designed for comfort and style. Made from a premium blend of 95% cotton and 5% spandex, they provide a stretchy fit that feels like a second skin. The wide elastic waistband features a modern design, ensuring no pinching or itching throughout the day. With a 3D contour shape pouch and no front fly, these boxers offer excellent comfort and protection. Additionally, the short leg design helps to prevent ride-up, allowing you to stay comfortable and confident all day long.

What We Like
Comfortable cotton blend
Stylish waistband design
No front fly for comfort
Short leg prevents ride-up
Tag-free for all-day wear
Buying Guide Image
Editor's Notes

During our hipster underwear trunk for men research, we found 256 hipster underwear trunk for men products and shortlisted 4 quality products. We collected and analyzed 995,239 customer reviews through our big data system to write the hipster underwear trunks for men list. We found that most customers choose hipster underwear trunks for men with an average price of £20.43.

The hipster underwear trunks for men are available for purchase. We have researched hundreds of brands and picked the top brands of hipster underwear trunks for men, including ANTONIO ROSSI, INNERSY, wirarpa.

Written by
John Zimmer Avatar

John Zimmer is a truly professional writer on findthisbest.com. He has specialized in writing content a wide variety of fields for over a decade. Since 2011, he has been using his expertise and extensive experience to write content for online shopping guide websites. In addition to writing for findthisbest.com, he has appeared in publications such as The Spruce, Wirecutter and Bestbuy.