The gentleman’s guide to dressing casually

It’s inevitable that in a gentleman’s life he will spend the majority of his day wearing uncomfortable attire consisting of restricting suits, shirts and ties. Being forced into the same clothes day in, day out, can be fairly tedious and not leave much room for personality or a signature style. It’s all too easy for this exact gentleman to slip into the terrible habit of, on the weekends, purely wearing tracksuits or something similar just because he’s been so uncomfortable that week. There are ways to dress casually without compromising your style, and here’s how:

Out with the old

When it comes to casual casual (we’re talking tracksuits), many men, unfortunately, assume that this consists of finding your most stained and worn t-shirt and tracksuits, alongside some old running trainers. If this is you, it’s time to reassess your style – in a big way. Instead of always heading for the aforementioned (frankly hideous) attire, you need to invest in some decent pieces that will up your style game to the level that every gentleman deserves to be at. James Perse and Derek Rose are two brands that we return to time and time again for exactly this, and we suggest you do too. Always stick to basic neutral colours such as grey, black and navy. Anything too outlandish will just look like you’re trying too hard. Cashmere is always a texture that we would recommend, for obvious reasons. And, if the clothes are right, don’t be afraid to wear the same colour in each item.

James Perse t-shirt, on sale at £77.50, James Perse trousers, on sale at £97.50

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Don’t ignore denim

If you’re looking for something besides tracksuits to wear, the best place to start is with jeans: the most universally casual item there is. While finding the right pair of jeans is undoubtedly a very difficult thing to get right, we are still surprised at how many horrendous pairs there are out there. Take it from us: anything purposefully distressed, ridiculously baggy or anything that goes past your shoes is a huge no-no.

You need to invest the time (and the money) in finding the right jeans for you. There are plenty of tailors in the world who can fix up any pair that you’ve brought but that aren’t the right shape and, even better, there are plenty of jean brands out there who will do this in-house and within a number of hours. Remember, also, that denim doesn’t always have to mean blue. Black jeans are just as useful – if not more – than regular denim and are the perfect place to start.

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Balenciaga jeans, £235

Your shoes still matter

Just because you’re not going to work doesn’t mean that you can ignore your shoes. Yes, you may be out of black brogues for a couple of days, but this does not give you an excuse to wear the ugliest shoes you can get your hands on just because they are comfortable (flip flops, we’re looking at you). If you’re heading out to the pub or on a more casual date, there are still so many comfortable – but stylish – options that you can go for. Again, it’s essential not to let your style take a back seat just because you don’t have any meetings to attend. Lanvin and Common Projects are two brands that get shoes right time and time again, and if you’re looking to hop on the casual shoe bandwagon (which we strongly suggest you do), these two brands are a great place to start. If you need some convincing, see here.

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Common projects trainers, £265

A blazer won’t cut it….

…Unless you’re going smart casual, which is a whole different story. You need to start to find the right kind of in-between and an option that will work well with jeans and a t-shirt as well as with your new casual tracksuits if you suddenly run out of milk and need to pop out. The first type of jacket that springs to mind is the bomber jacket: an item that made a serious comeback a few years ago and has very firmly remained at the top of its game ever since. This is the perfect piece to wear, not only because of its functionality but also because of its style. It basically acts as the perfect balance between a hoodie and something much smarter, like a blazer. Oliver Spencer and Folk are two brands that do the bomber seriously well, and are both brands that we’d recommend whole-heartedly. Try not to wear anything else too boxy or baggy with a bomber. You want it to stand out on its own, without being over-shadowed by anything else over the top – and don’t wear matching colours, either.

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Oliver Spencer, on sale at £171

If in doubt…

Look to the celebrities that do it best for your style inspiration. These guys may often have some of the best stylists in the game, but for their more casual appearances it’s more than likely that they’ve dressed themselves. Remember, these gentlemen have access to some of the best clothes in the world, so it’s pretty safe to trust their taste. Daniel Craig, Eddie Redmayne and Bradley Cooper are three gentlemen who do casual very well indeed.

BRADLEY COOPER as Phil in Warner Bros. Pictures’ and Legendary Pictures’ comedy “THE HANGOVER PART III,” a Warner Bros. Pictures release.

India Gladstone

India Gladstone

India is the Online Editor of Gentleman's Journal

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