Men's Chelsea Boots Outfits You'll Want To Copy Right Now

By Annabel van Eijk | Styles | 07/01/20
4 Men's Chelsea Boots Outfits

Men, I don't know how to put this but I think I need to be straight with you. You need a pair of men's Chelsea boots. Seriously, no excuses. Its time to swap those beaten down trainers for a pair of sharp, stylish and utterly cool boots. 

I really do feel that men's Chelsea boots outfits are as easy to put together as that one pasta recipe you impress people with, yet are rarely utilised by the men amongst us. You will look put together and stylish without looking too uptight or posh like most loafers or brogues will do. Chelsea Boots, have a certain je ne sais quoi that will turn any man into the kind that seriously has it all together. Yes, it really is that simple. But if you need a little more convincing I've put together these 4 men's Chelsea boots outfits for you to copy just to show you how versatile these shoes truly are. 

The Best Men's Chelsea Boots

Ok, before we head right into the outfits you may need a little guidance as to what  Men's Chelsea Boots you should buy. If you've read my blog on What Your Shoes Really Say About You you may have noticed I'm a serious fangirl of these shoes. So I also know a thing or two about what's out there and let me tell you, there's plenty for you to choose from. The best men's Chelsea Boots can be found anywhere from your favourite high street brands to classic shoe brands and designer labels. You can go for a sleek, streamlined style or a sturdier staple like Dr.Martens Men's Chelsea Boots. Common Projects Men's Chelsea Boots are always a good go-to for footwear, while Church's Men's Chelsea Boots will have you looking tip-top in luxurious leather styles. 

Men's Chelsea Boots Outfits

For the Snazzy Suit Guy 

Oh, ok so you're the big guy around here? Well, you better start dressing the part and I can't think of a better, more stylish way than to do so with this men's Chelsea Boots Outfit for men. These shoes are perfect to refresh your suit look without losing that sharp, tailored feel. It says you're not just a businessman, but a cool businessman. Sometimes, sneakers work great under a sharply tailored ensemble but there is a risk of looking too gimmicky, Chelsea Boots still have a dapper feel and under a suit, add just a glimpse of unexpected vigour. Swap the white shirt for a sleek turtleneck and you've really got the whole meeting room at your feet. 

Since Chelsea Boots never really come in bold colours, you can pretty much pick any suit and any pair of Chelsea boots. In particular, I think a grey suit and black boots are a good match as well as a black suit and dark brown or burgundy boots

Chelsea Boots Outfit 1

For the Modern James Dean 

You're a rebel without a cause, roaming around the city looking for trouble - at least that's what you look like and maybe a little less of a criminal feel and more criminally handsome *wink wink*. We've seen plenty of style icons like Kit Harrington (aka the one and only Jon Snow) and Harry Styles (aka the most stylish man on the planet) owning this look, and it really shouldn't be too tricky for you to do the same. Chelsea Boots teamed with skinny black jeans and a classic trucker jacket gives off a retro masculine feel that takes zero-effort yet looks a 100% stylish. You'll look confident and nonchalant with a rugged appeal but the Chelsea boots will make it much less scruffy. 

Chelsea Boots Outfit 2

For the Man About Town

If you're always at the right place at the right time, know all the hotspots and somehow always have someone gorgeous tagging along with you then this is the outfit for you, or it's the outfit to make you at least look like that guy. This men's Chelsea boots outfit has a dapper, dressed-up feel but not as uptight as a suit. You can wear this while you sip on whiskey in the latest hyped-up bar or to that chic house-warming you know your ex will be at to impress. This outfit is really about finding a good per of pants, by good I mean sharp and well-tailored - it will make all the difference. A short-sleeve shirt gives off a masculine nostalgia, topped off with a stylish Fedora hat and you're the man of the hour.

Chelsea Boots Outfit Men 4

For the guy that keeps his cool


Chelsea boots may look they ooze a certain sophistication, but really, they can be very laidback and can be worn with any dressed-down outfit. Free time doesn't mean you're free from looking chic and tidy, aka it doesn't mean you should be slouching around in your old Vans as soon as the weekend hits. Swap those sloppy trainers for a pair of slightly heeled boots and you'll be keeping your cool in this off-duty look. I'd say, go any of your favourite jeans and throw over a cosy knit jumper, sweater or when it's summer just a T-shirt or short sleeve button up shirt will do. Finish it off with a flat cap and you're looking very David Beckham ( now who would say no to that?). 

Chelsea Boots Outfit 3

There you go, 4 fool-proof men's Chelsea boots outfits that you can copy easily and, hopefully, will want to copy right now. 

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