Is It Time To Refresh Your Undies? These 12 Underwear Styles Offer The Most Comfort

By Dan Ahwa
Viva
Fitness influencer Steven Kelly wearing a pair of Skims boxer briefs launched in May. Photo / Skims

Cost per wear doesn’t mean you need to walk around wearing a pair of undies falling apart at the seams. Fashion director Dan Ahwa road-tests 12 underwear styles and gives us his feedback.

The softness that comes with garments that age over a period time is often the reason why

A T-shirt from high-school with its perfect holes and slouchy shape is no competition to a box-fresh pyjama top at bedtime. A pair of rugby shorts worn down to a breezy texture will often serve as the perfect accompaniment to a weekend of mooching about at home or pottering in the garden.

Clothes have memories imbued in them. But when a pair of torn and tired undies become a normal part of your everyday routine of getting dressed, it’s time to reconsider the decisions you‘re making in life. Starting with your underwear drawer. I’m talking specifically to the men in the room here. Women’s undergarments require their own set of rules and regulations that would make border patrol blush, and my more experienced colleagues have offered up their helpful recommendations and suggestions for which undies to shop for varying body shapes to a range of very good bras to try and buy.

Nisa's popular Jules boxer briefs are sustainably and ethically produced in Wellington.
Nisa's popular Jules boxer briefs are sustainably and ethically produced in Wellington.

I recently had to get rid of a pair of cotton trunks I’d unconsciously hoarded for at least a decade, perfectly softened over time. While my updated collection of undies made their mark, that old pair would now and then make a cameo.

Technically we’re meant to update our undies every 6-12 months. But it’s easy not to subscribe to that kind of wardrobe frequency for a garment no one can see except for you and your significant other.

Yes, it’s too much information, but consider it a cautionary tale.

Men, let’s not normalise the need to hang onto those worn-out undies and consider a cyclical investment of fresh ones that do everything they’re designed to do – provide support, whether you’re sitting on a long-haul flight or doing lunges up Mt Everest; along with cooling us down when we get too hot and keeping us snug when temperatures plunge.

It helps if they look good too, and the below assortment of undies I have tried and tested across the past two weeks primarily focusing on the things that make the perfect pair – a not-too-restrictive waistband, seamless stitching so you don’t have to deal with irritation, and support for a range of temperatures.

How could I not resist trying this pair on with its declaration they’re “the best undies you’ll ever wear”. With its easy top stitching, this cotton option is sized from small to 2XL and has that seamless feel that I’ve come to appreciate more recently. The black pair has been put to good use but if I was to go for a second, I’d suggest a classy merlot. Acting like what shapewear is for women, the clean, minimalist lines of this option are great for providing a subtle, tidy fit.

Because men’s undies are a cyclical purchase, these undies introduced me to the possibility that men’s underwear can actually be comfortable. My first pair purchased in 2018 has lasted the course of the past six years, living through a pandemic and a recession, with only a couple of tears in the inner leg where the built-in TENCEL™ Lyocell and 6% spandex has become visible. My fresh update in grey is a great option for a regular day at the office. Also made with 56% organic cotton, there’s plenty of breathability and the moisture-wicking properties of this fabrication make it an ideal option for men on the go. If you’re a frequent flyer, these really are comfortable to wear – you don’t have the restrictiveness that comes with a pair of briefs and you don’t need to deal with the superfluous cotton boxer shorts.

A personal big fan of this locally made Wellington label. Comfortable and easy to maintain, the Jules boxer brief is made from 95% certified organic cotton knitted in Melbourne and 5% spandex. They come in an array of fun colours, but I opted for this blue pair to break up my collection of black underwear. Offering ethical manufacturing from sampling through to production runs, the brand has changed the game in terms of combining social impact with a wardrobe essential we often take for granted.

I’m normally not a classic cotton boxer short kind of guy during the week, but on the weekends I live in them. I do think the quality of cotton matters when you are the type of person who likes the freedom of a boxer short, and these did not disappoint with the double-turned seams, an open fly and a soft elasticated waistband. Often boxer shorts come with waistbands that are fastidious and bunch, leaving marks around your torso, but these slip on and off with subtle ease. Made from beautiful 100% soft cotton, these are boxer shorts that will last you well.

This is a signature style from the underwear stalwart and this recent update was a welcome reminder of Jockey’s position in the market as a leader in men’s underwear. My favourite though is not its classic Y-front briefs or its array of patterned options (by all means if you like a printed pair of undies go ahead) but it was these lightweight “No Ride Up” trunks that came out on top. They shape well to the body and the absence of back seams gives them a very smooth finish. Super comfortable and the bound leg lines offer plenty of support so your undies don’t bunch and ride up.

For another easy woven boxer short alternative, I have looked to try something a little more affordable and this pair of Cotton On ticked several boxes for me. The preppy stripes, the tidy elasticated waist. Made with 97% cotton material for breathability, I found these an ideal option even for my working week as they were more streamlined than most woven boxers. Great underneath dress trousers for a smooth finish.

Another underwear reliable, Bendon’s range of options for men is wide and varied, including some ideal options for active men who require performance-enhancing undies. The best though is a simple pair of bamboo-infused antibacterial trunks with a soft elastic waistband and subtle logo design. What I liked about this was how simple and ergonomic the design is. Clean-cut, my black pair is a great investment but my second option would be the soothing colourway of “Kombu” green. It also sits perfectly with a hemline that skims my mid-thigh.

Kim Kardashian has created a surprisingly unique proposition in the underwear and lifestyle category with her Skims brand, and for my first try on of her men’s line of underwear, I opt for this sleek pair of boxer briefs made from a very soft and stretchy fabric made up of 91% modal and 9% elastane. To be honest, these did feel like a second skin, which is what the brand has done particularly well – targeting undergarments that feel lightweight, barely there. Sleeping in this pair was extremely comfortable.

The last time I can remember wearing briefs was when I was 10, so for the purposes of this collection I made a return to the style with something classic. While I tried a couple of other brief variations, this one stood out for its seamless appeal – in fact, I didn’t feel restricted at all. The brand has been synonymous with quality underwear and sleepwear since the 1920s, so I had high hopes for these. With a focus on stretch, this mid brief is cut high on the leg and finishes mid-height on the waist. What I loved the most was how they were made from a butter-soft blend of 92% Pima cotton and 8% elastane, which extends to cover the waistband (ideal). The hems are all finished with super-soft binding which makes this a simple, minimalist but highly-designed underwear to last the distance.

The local menswear brand is an ideal port of call for professional white-collar workers who need a one-stop shop for shirts, ties and work trousers. If you need a smart pair of boxer shorts, I found this loose-fitting pair really comfortable to wear for work and weekend. Crafted from the brand’s line of soft shirting material, the 100% woven cotton boxer shorts feature helpful side vents, a button-fly front and have a slightly vintage appeal – resembling old-school boxing trunks with soft pleats at the front for unrestricted movement. This soft pink is also a great addition of colour to an otherwise conservative wardrobe of neutrals.

Who doesn’t like a multi-pack underwear offering? You get three of these classic briefs from the underwear favourite. Over the years I’ve tried and tested several of Calvin Klein’s options, and while a high-cut brief is not my first choice, I decided to give these a go and compare them to my faithful Calvin Klein boxer briefs. Made from a soft microfibre jersey, what I liked about these was how they sat on my hip and were supported by a generous elastic waistband that didn’t dig into my skin. Made from 88% recycled polyester and 12% elastane, the best part of this option is how silky soft the surface is. Great for professional and formal occasions when you need slick underwear that doesn’t add too much bulk to your silhouette.

The sustainable leader offers one of the best underwear styles on the market made with 89% recycled nylon and 11% spandex pique mesh; it also features elements of miDori™ bioSoft for added wicking and softness, and HeiQ® Pure odour control – so consider these a highly technical fabrication that will offer you maximum support. Made in a Fair Trade Certified™ factor, what I love about wearing performance boxer briefs as everyday underwear is that added feeling of knowing that you’re wearing something that will not let you down, whatever the situation. The detail of flatlock seams is another bonus point for me, offering additional comfort that all men need in their underwear.

Dan Ahwa is Viva’s fashion and creative director and a senior premium lifestyle journalist for the New Zealand Herald, specialising in fashion, luxury, arts and culture. He is also an award-winning stylist with more than 17 years of experience, and is a co-author and co-curator of The New Zealand Fashion Museum’s Moana Currents: Dressing Aotearoa Now.

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