The Comfortable (Yet Stylish) Clothes Every Modern Man Should Own

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.

Heavyweight T-Shirt

A cheap, paper-thin T-shirt clings in all the wrong places and loses its shape after one wash. A heavyweight T-shirt, on the other hand, provides structure, durability and comfort without sacrificing breathability.

Look for one in a mid-to-heavyweight cotton jersey—ideally around 220 – 300gsm—for that perfect balance of softness and longevity. It drapes better, holds up over time and feels more substantial without being bulky.

Unstructured Blazer

A traditional blazer can sometimes feel a little stiff—both in construction and in comfort. Enter the unstructured blazer, a softer, more relaxed alternative that ditches the padding and rigid formality while still keeping you looking sharp.

Typically made from lightweight wool, cotton or linen, an unstructured blazer moves with you and feels as easy to wear as a cardigan. Combine it with drawstring trousers and a merino tee for a smart-casual look that prioritises comfort without sacrificing style.

Elasticated Waist Shorts

Tailored shorts look great, but they’re not always the most comfortable choice. That’s where elasticated waist shorts come in. They provide the ease and flexibility of gym shorts while maintaining a refined, structured appearance that works in various settings.

Look for styles in breathable fabrics like linen, cotton twill or Tencel and wear them with a lightweight button-up or a polo for a relaxed yet polished warm-weather look. Whether you’re on holiday or just lounging around on the weekend, these are the shorts you won’t want to take off.

Jersey Button-Up Shirt

A classic Oxford shirt can feel stiff and restrictive, but a jersey button-up gives you the same smart look with the comfort of your favourite T-shirt. Made from soft, stretchy cotton jersey, these shirts have a natural give that moves with you, making them perfect for long days at the office or casual weekend wear.

Pair one with tailored drawstring trousers and minimal sneakers for an outfit that looks polished but feels effortless.

House Slippers

There’s a fine line between loungewear and looking like you’ve given up entirely, and a good pair of house slippers will keep you on the right side of it. Forget flimsy hotel freebies—invest in a proper pair made from suede, leather or cashmere-lined wool.

Brands like Mahabis, Birkenstock and Derek Rose offer stylish options that work whether you’re padding around the house or making a quick trip to the corner shop.

Comfort starts at home, and a pair of quality slippers is a game-changer.

Relaxed-Fit Chinos

For too long, slim-fit chinos were the default choice for men’s casual tailoring. Thankfully, the tide has now turned toward looser, more forgiving cuts. A pair of relaxed-fit chinos gives you room to move, breathe and actually sit down comfortably while still looking smart enough for most occasions.

Opt for a straight-leg or slightly tapered silhouette and wear them with everything from polos and sneakers to knitwear and loafers. Bonus points if they’re made from a stretch-cotton blend for extra comfort.