Boots are probably considered one of the most casual designs among the Goodyear Welted classics in one’s wardrobe. Rightfully so, but the humble boot works surprisingly well even with tailored outfits intended to wear around town, even in the depths of winter.
It sounds simple, but the key to investing in the right kind of boots for you is to determine which style will be most versatile with your wardrobe. If selvedge denim is one of your wardrobe staples, you might consider a more casual boot such as the Coniston or Islay, both of which have a touch of ‘workwear’ design influences about them. The double Dainite soles and storm welts emphasise each boot’s casual nature and together with Crockett & Jones’s Dark Brown Scotch Grain they are a perfect match against rugged indigo.
Another casual option that I love but rarely wear with formal tailoring is the Chelsea boot. Its sleek silhouette and lack of laces makes it slightly more rock ’n’ roll than your average lace-up boot. With a suede jacket, a rollneck and slimmer jeans they are the perfect fall/winter option.
For those who fancy a more sartorial look, with a tailored jacket and flannel or whipcord trousers, I’d suggest going for a slightly smarter option like the much-underrated Balmoral boots. From a distance they will resemble a classic Oxford shoe, but of course enclose the makes to help keep your feet warm during the biting winter months. This look was quite common back in the 1920s and ‘30s when Balmoral boots were often an accepted choice with suits.
Speaking of tailoring, you might find it hard to combine a sturdy boot with something as formal as a suit, but it all comes down to details. While a dark worsted suit screams for black toe-cap Oxfords, a grey flannel suit looks fantastic with a pair of sleek brown suede boots. If you don’t believe me, Google il maestro, Gianni Agnelli. The former Fiat chairman and entrepreneur is considered the best dressed man in history by many guys in-the-know, and with stylish quirks (like rugged suede boots paired with Huntsman or Caraceni suits) he inspired generations of men to embrace ‘sprezzatura’ as a way of dressing.
Now, let’s be clear. We are not Gianni Agnelli, but we can all take note of his daring wardrobe combinations. Instead of a classic shirt and tie, I’d combine my flannel suit and brown suede boots with some heavy knitwear, for example. If the classic cap-toe boot is not to your liking, I would consider the timeless Chukka. It is a surprisingly versatile style worn with casual tailoring and especially in mid-brown suede.
One thing worth mentioning is the soles of your boots, because they influence the boot’s overall aesthetic more than you might imagine. Thinner single leather soles will always look more elegant than a chunky rubber Dainite or Commando sole, but the latter will be more practical in winter, and better insulate your feet from the cold.
In short, not all winter boots are made equal, but do they all fulfil a purpose.