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Top 10 Most Comfortable Clothes For Men That Are Still Stylish

  • Sep 29, 2023
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Top 10 Most Comfortable Clothes For Men That Are Still Stylish

It’s all well and good looking cool, but if it comes at the expense of comfort, it’s going to show. The great Hardy Amies once said, “a man should look as if he has bought his clothes with intelligence, put them on with care and then forgotten all about them”. But it’s difficult to forget when you can’t properly sit down because your trousers are too tight, or when your shoes are pinching in all the wrong places.

What you need then are stylish clothes that look as good as they feel. Forget hard to break in raw denim, why not go stretch? High-waisted, pleated trousers that cut into your stomach? Go for a drawstring pair instead.

There are a number of pieces these days that prioritise comfort as well as style, but these just might be the best.

Drawstring Pants

There’s not much we can say about drawstring pants that we haven’t already. In short, they might be the only trousers you need. From a comfort standpoint they are unmatched. The elasticated waistband expands and contracts with you as you move and sit, in the same way a pair of sweatpants does. It’s a feeling that fixed waistband trousers just can’t match, and once you try it for yourself it will be difficult to go back.

But the real beauty of a good pair of drawstring pants is that they look like regular trousers. You’ll likely be the only person that knows they’re elasticated. That means, like chinos, they can be dressed up with a blazer and shirt, or worn more casually with a simple white tee and sneakers, yet they’re far more comfortable.

Cashmere Sweater

While cotton and merino wool are excellent choices when it comes to knitwear, cashmere is unmatched. The famously soft fabric, trimmed from the backs of specialist goats, typically native to the Gobi desert and Central Asia, represents the ultimate in luxury, making for some of the most comfortable sweaters money can buy.

Yes, it can be an investment, but as soon as you pull one on it’s easy to see why. Cashmere lives up to its premium price tag thanks to its beautifully soft handle, making it difficult to go back to plain old itchy lambswool once you’ve experienced it.

Silk Robe

A silk robe is one of those extravagant pieces that’s nice to have, but certainly not a necessity. Silk is expensive and delicate after all, so it might seem more hassle than it’s worth. But try a silk gown on and you’ll immediately see what all the fuss is about.

For wearing around the house, on lazy mornings and relaxed weekends, there is no more stylish or comfortable garment. Put it on first thing and it’ll almost feel cold to touch, while the delicate, silky-smooth fibres feel great against the skin.

What’s more, silk gowns come available in all manner of wild colours and patterns, from polka dots to tropical foliage prints, so you can spice up your loungewear with ease.

Lyocell Underwear

Forget cotton, if you’re looking for the most comfortable underwear around then consider lyocell. This relatively new fabric has exploded in popularity over recent years, in part due to its stellar eco credentials. Derived from trees, pulp is collected, dissolved and then reworked into fibres, creating a truly sustainable material that offers the smooth, soft feel of silk yet retains the durability of cotton.

It’s also a natural performance fabric, drawing moisture away from the body to help keep you cool, dry and comfortable all day long – everything you would ever want from your underwear.

Knitted Hoodie

If this was your first hoodie purchase, we’d recommend a classic cotton-jersey version for all-out versatility. A casual staple, they’re the perfect match for jeans and sneakers on the weekend and have long been the go-to of many a subculture over the last century. In short, they can’t be beat when it comes to day-to-day dressing.

If you’re looking for all-out comfort, however, a knitted version is the way to go. Typically constructed from merino wool or cashmere blends, this is the knitwear style you didn’t know you needed.  Offering a slightly smarter feel than a cotton or loopback version, try teaming your knitted hoodie with tailored trousers, unstructured blazers and other smart-casual staples for a sophisticated take on high-low dressing.

Merino Knit T-Shirt

Speaking of merino wool, it works well for T-shirts as well. While a regular, cotton jersey tee might be the obvious choice, one made in merino looks sharper, offers a tailored fit and is arguably more comfortable.

Merino wool is taken from the sheep of the same name, which is known for fibres that are softer and less coarse than regular wool. The resulting fabric feels gentle against the skin, but it’s also moisture wicking and temperature regulating too, making it ideal for keeping you cool in warmer weather. There’s a reason a lot of performance tees are made from this wonder fabric.

Brushed Cotton Shirt

Sure, an Oxford shirt is a menswear staple and one practically everybody should own. It’s easy to wear, goes with virtually everything and works all year round. But if you’re on the hunt for a shirt that’s softer and more comfortable, yet equally stylish, you should consider a brushed cotton design.

Usually slightly heavier than Oxford cloth, brushed cotton gets its texture from – you guessed it – being brushed to create a soft, fluffy nap that feels supremely soft against the skin. What this means to you is that you’ll have a garment that looks like a regular shirt but feels like a perfectly worn-in cardigan.

Vintage Running Shoes

Modern-day running shoes are some of the most comfortable trainers you can buy. The tech utilised in them is literally designed to keep your feet as supported as possible for running long distances, so they make light work of casual weekend walks and daily commutes.

Trouble is, due to the amount of tech incorporated, they aren’t particularly stylish. And when worn as part of a casual getup they can stick out for all the wrong reasons. That’s where retro running shoes come in. While not as technologically advanced as their up-to-date brethren, these vintage runners look as good as they feel, with their classic designs providing the perfect finishing touch to a range of laid-back looks.

Stretch-Denim Jeans

Most denim heads will tell you to invest in raw selvedge denim. And for good reason. It’s the purist’s choice, and no other fabric fades or takes on such a unique character over time. But it’s usually very stiff and difficult to break in, making it extremely uncomfortable for those first 6-12 months.

Stretch denim on the other hand is soft and pliable straight off the rack, meaning you can wear your favourite cut of jeans all day long without feeling denim fatigue. Go for a pair of straight-fit or tapered stretch jeans and they’ll almost feel as comfortable as sweatpants, without sacrificing much of the iconic look of traditional selvedge denim.


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