Although here in the UK we are currently revelling in the last few weeks of summer, other places across the globe aren’t quite as fortunate. Many sartorially-inclined men in more northern territories are already facing up to the fact that they will need to break out the heavy duty knits, boots and overcoats in the very near future.

And with winter fast approaching, situations often arise that would not normally occur if you lived somewhere akin to California. With this in mind, one of our loyal readers was kind enough to highlight one particular issue that I’m sure many others will have experienced:

Hi FashionBeans,

Since winter is coming soon, is there any way to wear boots with a suit? I live in Canada, where we get a lot of snow, slush, salt and cold weather.


It’s an excellent question. Most stylish individuals know to invest in quality footwear, and after a couple of years will have curated a respectable collection. I’m thinking black Derbies, tan brogues, brown Oxfords and oxblood penny loafers for formal events, along with a handful of trainers and suede styles for more casual occasions.

And although they’ll probably never admit to it, they’ve also got a pair of really ugly Wellington/hiking boots that they have ready for when the weather takes a turn for the worse.

However, the trouble with ugly Wellington/hiking boots is that they really don’t look right when put next to formal pieces such as a suit, as Alex mentions. So how exactly do you marry together these seemingly polar opposites on the sartorial scale? Well, it’s not as difficult as you might think.

The Right Type Of Boot

Firstly, not all boots are created equal. For a few years now, brands and designers at every price point have been creating stylish winter boots in a more sleek and simplified silhouette.

Gone are the outrageous huge treads in rubber soles, square toes and endless loop holes for needlessly long laces. In are durable yet soft leathers and classic colours and designs based on formal business shoes.

By adopting the characteristics of traditional formal silhouettes, this new generation of ‘dress boot’ is able to effortlessly pair with any tailoring you already own. Because, let’s face it, as soon as your trousers are on the hem will cover up the fact that it’s a boot and your outfit will look exactly like it does the other 90 per cent of the time.

Secondly, a chunky sole can be stylish as well. There’s a difference between the sort of sole that comes with a hiking boot and the sole that is found on a dress boot. Whether it’s a crepe, vibram or lug sole, all of them are super comfortable and really on trend right now, especially when paired with similar heavy duty pieces like tweed trousers, flannel shirts and denim jackets.

I would personally stay away from a thin or leather sole due the lack of traction it will give you when trying to traverse the wetter, slushier elements.

  • Ben Sherman Cleg 6-eye BootsBen Sherman Cleg 6-eye Boots
  • Kryton Kg Kurt Geiger Brown £130.00Kryton Kg Kurt Geiger Brown £130.00
  • Ted Baker Sealls Brogue BootsTed Baker Sealls Brogue Boots
  • Hemming Wc Grain Boot H By HudsonHemming Wc Grain Boot H By Hudson
  • He By Mango Lace-up Leather Ankle BootsHe By Mango Lace-up Leather Ankle Boots
  • Clarks Originals Leather Desert BootsClarks Originals Leather Desert Boots
  • Mark Mcnairy Suede Desert BootsMark Mcnairy Suede Desert Boots
  • Ben Sherman Deon High BootBen Sherman Deon High Boot
  • Scanzo Tc Boot Oliver SweeneyScanzo Tc Boot Oliver Sweeney
  • Tods No_code Crepe-sole Leather Chelsea BootsTods No_code Crepe-sole Leather Chelsea Boots
  • Campanile Class Leather Brogue Boots 166808Campanile Class Leather Brogue Boots 166808
  • Tods Leather Desert Boots 168973Tods Leather Desert Boots 168973
Keep It Simple

When looking to combine your new boots with a suit, you only need to remember one thing: KISS (Keep It Simple, Stupid). The fact you’re wearing boots with your suit is a big enough step as it is, so ease the transition by ensuring things remain as classic and neutral as possible.

For the boot, opt for black, brown or oxblood colour ways in Oxford, brogue or Derby designs. For the suit, stick to timeless colours paired with classic menswear pieces such as a white dress shirt and a navy knitted tie.

However, due to the connotations that come with wearing a pair of heavy duty boots, make sure that the material of your suit is suitable in texture too – think worsted wool, tweed or corduroy.

But above all else – wear the hell out of them! I know most people tend to be precious with their footwear (quite rightly so) but these are boots we’re talking about. Yes, they’re a little bit fancier. And there is no excuse not to clean them, polish them and store them properly.

All I’m saying is this: if you’ve invested in quality – be it denim, corduroy or leather – the more worn in it looks, the better. It adds character, individuality and distinctive qualities to an item that, otherwise, could be worn by hundreds of other people on the street. Make your clothes your own.

Lookbook Inspiration

MEn's Boots With a Suit Lookbook

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Final Word

So there you have it, a quick but conclusive guide to wearing boots with a suit. Is this a look that you’ve worn before? Do you think it works? If not, what would be your go-to choice of footwear for the winter season?

Let me know in the comments section below…

Matt Allinson