Men's Underwear Guide
Our Men’s Underwear Guide is designed to help you find the perfect fit, fabric and style for everyday comfort. From the natural softness of Pima cotton to the smooth stretch of micro modal, each material offers its own benefits — whether you prefer the freedom of boxers, the support of briefs or the balanced fit of trunks. With expert insight into cuts, fabrics and waistband finishes, this guide shows how intelligent design and meticulous craftsmanship come together.
At Derek Rose, we design underwear for how life feels — quietly luxurious pieces that sit close to the skin without ever asking for attention. Each style is shaped by decades of craft, refined with modern fabric innovation, and finished with the kind of considered details that make comfort feel effortless.
Whether you prefer a slim, supportive fit or an easy, free-moving silhouette, here’s a closer look at the styles we make — and why they feel quite so good.
New
CLASSIC FIT BOXERS
- Relaxed-fit boxer shorts for easy movement and breathability.
- Fabric-covered elastic waistband that sits softly on the skin.
- Adjustable two-button waist for a tailored, personal fit.
- Keyhole fly for traditional functionality and everyday ease.
The classic boxer is our ode to timeless comfort: relaxed, airy and beautifully made. The fabric-covered elastic waistband sits softly on the waist, while the adjustable two-button fly brings a touch of traditional tailoring. They’re designed to move easily under trousers — never bulky, always breathable. Available in cotton or silk.
Perfect for those who enjoy a little extra room to breathe.
New
Sold out
Sold out
Sold out
MODERN FIT BOXERS
- Regular-fit boxer shorts offering a clean, contemporary silhouette.
- Fabric-covered elastic waistband for all-day comfort.
- Curved hem for improved movement and a refined shape.
- Magnetic fly closure for smooth, effortless functionality.
For those who enjoy the openness of a boxer but prefer a cleaner silhouette, our modern fit bridges the gap. The regular cut offers subtle shaping without losing ease, while the curved hem gives a refined, contemporary line. A magnetic fly closure adds a discreet, modern detail — precise, smooth and quietly satisfying.
For wearers who want tradition, thoughtfully updated.
Sold out
TRUNKS
- Slim-fit trunks with a slightly longer leg for confident coverage.
- Fine-gauge, skin-soft jersey offering comfort and flexibility.
- Fabric-covered waistband that sits smoothly against the skin.
- Keyhole opening and welted hem for ease and a clean line.
Trunks are our contemporary essential — cut slim with a slightly longer leg for confident coverage and a clean line under clothing. Made from our skin-soft, fine-gauge jersey, they feature a fabric-covered waistband, a welted hem for a smooth finish and a keyhole opening for ease.
Great for those who like the feel of a brief with the assurance of a little more length.
BOXER BRIEFS
- Slim-fit hipster cut with a clean closed front.
- Crafted from skin-soft, fine-gauge jersey for breathable comfort.
- Fabric-covered waistband for a smooth, irritation-free feel.
- Welted hem for a neat, refined finish that stays comfortably in place.
Our boxer briefs sit slightly lower on the waist, offering a natural, easy fit. They’re cut from cotton, Pima cotton or micro modal — a breathable, moisture-wicking fabric chosen for its exceptional softness. If you enjoy underwear that feels almost weightless yet still supportive, hipsters are a particularly inviting choice.
Ideal for those who like the structure of a brief with the coverage of a short.
BRIEFS
- Slim-fit brief with a streamlined closed front.
- Skin-soft, fine-gauge jersey for stretch, breathability and daily comfort.
- Fabric-covered waistband for a soft, non-irritating feel.
- High-modulus binding at the leg for a secure yet gentle hold.
Slim, supportive fit that offers gentle structure without restricting movement. Closed front design for a clean, streamlined silhouette. Skin-soft, fine-gauge jersey that feels smooth, breathable and lightly stretchy against the skin. Fabric-covered waistband for a soft, irritation-free finish. High-modulus binding at the leg to keep the fit secure and comfortably in place throughout the day.
Perfect for those who prefer a clean, supportive fit that stays discreet and comfortable under any outfit.
UNDERSHIRTS
- Flat, fabric-covered seams to minimise bulk and irritation.
- Lightly elasticated rib trims that hold shape without digging in.
- Naturally breathable jersey that keeps you comfortable through temperature shifts.
- A smooth drape that layers cleanly under shirting, knitwear and loungewear.
- Available in a v-neck t-shirt or vest.
Our Pima cotton undershirts are designed to bring effortless comfort to the everyday, whether you prefer the discreet structure of a V-neck or the freedom of a sleeveless vest.
The slim-fit V-neck T-shirt sits smoothly beneath shirts thanks to its low neckline, fine-gauge jersey and long-body cut, all finished with soft, narrow binding and a clean welted hem.
The vest offers the same luxuriously soft feel with a scoop neck, deep armholes and a shape crafted for natural movement and breathability. Whichever style you choose, each piece is thoughtfully made to sit close to the skin, layer without bulk and keep you feeling comfortable from morning to night.
Perfect if you prefer a fitted base layer that moves with you and stays out of sight.
