Men: How To Dress Smart & Upgrade Your Casualwear

Written by Bronwen | 28/02/2020


How To

How do you upgrade your casualwear? It can be easy to dress a little scruffy when we’re just going about our day-to-day, and a t-shirt paired with jeans looks just fine, but it doesn’t look incredibly stylish.

From simple accessorising to purging your wardrobe. Here we go through the little tips and tricks you can easily do to level up your casual style.


In the words of our Lord and saviour, Marie Kondo, throw out any casual clothing that doesn’t “spark joy.”

None of your clothes spark joy? Well, I’m not saying get rid of the majority until you have a minimalistic wardrobe (we’re not going that extreme, yet) but there are bound to be a few things that would be better off in a charity shop (or maybe even the bin). Offenders include:

  •  Any clothes with holes or tears – yes, that includes your favourite t-shirt you’ve worn for a decade.
  •  Anything with unwashable stains.
  • Anything you haven’t worn for over a month – unless it’s weather dependent if you’ve ignored a casual piece of clothing for this long, chances are you just don’t need it.
  • Faded clothes that are looking a little old and worn – even if they’re not exactly ruined, these clothes will never look anything more than slobby, demote them to pyjamas or send them to a charity shop.

The idea of this tip is that it will eliminate the choice paradox. Too often we look in our busy wardrobes and declare that we have nothing to wear. Purging our closet of the useless clothes, that we simply don’t look good in anymore, will leave everything you’ve kept with a purpose.

A shirt, green trousers and white t shirt laid out on the floor neatly

[Image: LifeStyleByPS]


Often, our casual clothes all look very similar. Every other man you walk past in town will be wearing jeans and a t-shirt. So, when you spot a stranger that’s dressed well, it’s usually because he will stand out from the crowd for reasons you simply cannot completely fathom.

No, it’s NOT because he has insanely niche and complicated clothes (well it might be, but not for our example) it is because he’s upgraded his casual wear by layering simple pieces together.

If you’re not sure how to layer, then don’t worry, we have a layering guide here.

3 Men in Layered outfits side by side.


Casual wear is not the same as leisurewear. You should never look sloppy, that’s why it’s a great idea to get a few of your favourite shirts and chinos tailored.

Tailoring is usually reserved for your smart wardrobe, but your casual wear can benefit massively from a bit of tailored attention.

I’m not saying all your clothes need to be taken in, but a few careful choices will really help make your casual clothes seem smarter. Mainly your chinos, trousers and a favourite shirt or jacket. If you’re not sure what trouser break you need when tailoring your trousers then the differences are labelled here.

A Blazer with white tailoring stictches

[Image: Norton & Sons]


We’re all guilty of wearing the same pair of straight cut dark jeans every day. And that’s because they look great! But if you want to level up your casual style then changing things down below is an easy option.

Leave the jeans at home every now and then and alternate between different coloured trousers and chinos. A top/shirt can always be pulled off with jeans, but it will help you stand out if you opt for some chinos for a change. Click here to see how your chinos should fit.

Man In Red Trousers Hugo Boss

The same rule can also go for your shoes! Ditch the dirty trainers (and clean them, please) and swap for some chukka or desert boots for a much smarter look.

Formal Shoes Lined Up

Want more styling tips for men? Check out our other ‘how-tos’ here.


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