Get your own personal stylist to help you find clothes you love. All online, completely free

Sign In

What goes with what

What does well-dressed mean?

What does well-dressed mean?

For all its supposed rules, style is still a highly subjective thing. An outfit that one man considers the height of refinement might, in another’s eyes, look over- or underdressed, oddly proportioned, or accessorised with all the taste of a Christmas tree. For all that men might idolise Don Draper, there is no platonic ideal of a great outfit; a slim, black suit is rarely the right answer in the real world. What’s right or wrong is individual, informed by our experiences, our taste in everything from film to music, even the opinions of our friends and family. Hence all those thousands of different brands, catering to everything from bespoke blazers to ripped jeans.

That’s why we personalise all our recommendations. Because style advice that doesn’t take into account the mores of the man wearing it isn’t advice at all. “There is no one ‘well-dressed look’,” says Thread stylist Alexander McCalla. “It’s not about being suited and booted. It can be any aesthetic. But there are some rules that dictate whether a style works, even for wildly different looks.”

Because this is the core of being well-dressed: it’s about wearing your clothes well. The items can, within reason, run the gamut from trendy streetwear to sober, timeless tailoring. Because if you make it look natural (and nail the constants below) then a man can look as sharp in a pair of joggers as he does in a tuxedo. Here’s how to be well-dressed, every day.

You know your best fit

Well-dressed fit

Photographed: M&S blazer (£139); Reiss shirt (£95); Oliver Sweeney chinos (£129); Timothy Everest tie (£65)

There is one big difference between ‘fashion’ and ‘style’ – time. Fashion lasts a few months; what we consider stylish hangs around for a decade. But both are impermanent. Suits, which we consider fairly impervious to the whims of fashion, changed between the 30s and the 50s, from baggy to trim – Fred Astaire to JFK. By the 1970s, they’d ballooned back out again, this time with added bell bottoms and oversized collars.

We look back now and shudder, but in 1975 you’d be considered old-fashioned if you wore one of today’s slim-fitting suits. All of which is to say that there is no correct shape for your clothes to be. But there is a correct shape for you. “You shouldn’t wear something that fights your body,” says Alexander. “You can make loose or tight clothes work, but it has to look deliberate.”

To be well-dressed, your wardrobe has to fit well. You can wear skinny or straight-leg jeans, but the waist and the cuff should be right. You can opt for the same boxy t-shirts as skateboarders, or a figure-hugging James Dean fit, but the shoulders should match your own. “It’s the basis for how you build an outfit,” says Alexander. “If you get it wrong then you can’t layer, you can’t make your proportions work properly, and your outfits won’t look appropriate.” The first step to being well-dressed is to grab a tape measure.

You wear colours that work for you


Photographed: Paul Smith jacket (£200); Wax London hoodie (£80); Stan Ray trousers (£75); Clarks trainers (£109); Masterpiece backpack (£125)

When colours work, you don’t notice them. When they don’t, it’s all you can see. “If you wear combinations that are wrong with each other, or with your complexion, you can’t look good,” says Alexander. Your clothes will clash and your skin will look lifeless. Your entire outfit will appear awkward no one will quite know why.

Again, this is an idea that straddles aesthetics. Nailing the shades of your suit accessories is as important as matching your t-shirt to your jacket. “It shows consideration,” says Alexander. “It’s the difference between wearing individual clothes and an outfit where they all work together.” To be well-dressed, everything needs to be in unison, from your hair colour to the shade of your shoes. “It also needs to be right to the environment. You should know when bright colours are inappropriate, or when you look boring if you’re in all-black.”

The best way to get this right is to be consistent. First, check out our breakdown of your best colours in your Style Summary. Then, stick to them. “If you keep to shades that you know work together, and with your complexion, then everything else becomes easier,” says Alexander. “Your outfit starts to gel.” It will also help you develop a signature style, which is the key to moving from not-getting-it-wrong to getting-it-right.

You dress for where you’re going

Creative outfit

Photographed: A Day’s March jacket (£110); H&M Edition shirt (£49.99); French Connection chinos (£84.50); adidas trainers (£79)

If great style was universal, we’d all wear tuxedos everywhere. But being well-dressed is as much about reading your environment as your wardrobe. Style is largely about the way that others see you and, to get it right, you have to meet people’s expectations. Turn up to a job interview in a Hawaiian shirt and odds are you’re not getting the gig, even if you tell them that hula girls are the year’s biggest trend.

“You have to understand the environment you’re in. The best outfits are built off that,” says Alexander. “It’s even simple things like knowing what to wear for the weather. If you’re sweating or shivering, you’re not going to look good, no matter how nice your outfit is.” This is where a knowledge of fabrics and layering pays off – to be well-dressed you need to think about the way your clothes interact with the world. If an outfit only works when you’ve got your coat on, then unless you’re spending the entire day outside, you’re not dressing well.

You wear your clothes with confidence

Heritage outfit

Photographed: Barbour jacket (£199); Armorlux t-shirt (£55); Edwin jeans (£140); MVP desert boots (£55); Timex x Nigel Cabourn watch (£129)

Confidence is the hardest and most important element of being well-dressed. “There are times when even an outfit that’s well put-together can be wrong if you don’t look comfortable wearing it,” says Alexander. That’s why the clothes on runways are so irrelevant to the average man – if you’re wearing something that makes you feel self-conscious, everyone can tell.

Confidence is about many things, but getting your fit and colours right first will help. “You’ll know that you’ve got the foundations solid,” says Alexander. “Then even pieces that stand out feel more comfortable.” That’s important, because trying things slightly out of your comfort zone is vital if you want your style to feel personal, not humdrum. A pattern, a interesting colour or shape, even a style that’s different to what everyone else is wearing; these are the things that set you apart.

Fortunately, there are ways to cheat your way to confidence. And once you fake it, you’ll start to feel it for real. “Stand upright and don’t fidget,” says Alexander. If you’re picking at your clothes then you’ll look uncomfortable, like a schoolboy who’s been forced into a suit. “You want to appear like you’ve thought about what you’re wearing, but not too much. A nonchalance that confidence plays into. If you look like you chose these clothes yourself – and chose them for a reason – then you’ll look good.” No matter what you’re wearing.