That questions come in every morning when you get ready for office. Despite their chunky soles and unforgiving leathers, winter boots are some of the most versatile shoes you can buy. Invest in the right pair of shoes and they’ll last decades if you look after them as much as they do you. So, best foot forward.
There are other, subtler ways to infuse your winter look with some outdoorsy influences. A sartorial hybrid, the brogue boot comes with the same reassuring weight and solid construction of hiking boots, but with all the wing-tipped smartness of brogues. As a general rule of thumb, you can wear your brogue shoes with any outfit you might normally wear with traditional brogues, so lace up a dark brown or black leather pair with heavier wool suiting, and smart trouser and shirt combinations.
While suede Chelsea shoes have something undeniably laid-back about them, it’s a delicate material that is hard to keep pristine in or just after a downpour. If you can’t be bothered with regular cleaning, brushing and applications of protector spray all winter, opt for easy-wipe leather instead. As it happens, a pair in smooth black leather is much closer to the iconic original anyway.
This in-between profile makes most ankle boots smart enough to style with a roll neck, blazer and smart wool trousers, but also not so fussy that they can’t be coupled with chinos and a crew neck sweatshirt. Perfect for navigating the winter months’ dress codes. Leather pair of shoes are a no-brainer for the cold and wet, offering resilience and enduring elegance, while suede pairs can also work if you take the time to regularly treat them with a protector spray and always check the forecast before you leave the house.