Rough and tough chukka boots from an iconic branda.

Check your calendar. And now look at the boots you’ve got on. Are they a stylish pair of leather boots for winter? Better yet, are they the Red Wing Heritage Classic Chukkas? No and no? Well, let’s fix that today via the latest entry in our See Now, Buy Now series. Here at The Style Guide, your author loves a classic, iconic brand like Red Wing Heritage for reasons aplenty, chief among them being the brand’s ongoing commitment to timeless styles and seriously tough construction. Those are both qualities that are going to serve you well this winter. And the Red Wing Heritage Classic Chukkas in particualr just get the job done, to say the very least. Finding the right pair of winter boots is a tricky endeavor in more ways than one — you want a pair that can stand up to snow and slush, yet you’re also going to need to be able to wear them in a myriad number of style situations (as you dress for the office or head to your favorite brewery, in particular). Again, the Red Wing Heritage Classic Chukkas deliver.

SHOP: The Red Wing Heritage Classic Chukkas via Bespoke Post 

Of note, they channel the same timeless construction and quality for which Red Wing Heritage is known, and the brand’s Minnesota roots sure do come in handy — the Red Wing Heritage Classic Chukkas feature an Atlas Tred outsole, plus nickel eyelets for durability throughout the chilly winter. While you might be better off wearing the Huckberry Duck Boots in an extreme blizzard, the Red Wing Heritage Classic Chukkas are as good as it gets the rest of the time. The plain toe chukka construction and briar oil slick leather are two touches that stand out subtly and stylishly, making them an easy bet to wear with everything from expertly faded denim and a grey crewneck sweater to your favorite henley and a tough waxed trucker jacket.

Of course, the Red Wing Heritage Classic Chukkas can also be dressed up ever so slightly — try them with the Billy Reid Bond Peacoat, plus a classic Oxford shirt and slim tan chinos, for Sunday brunch or even a day at the office. Yes, Red Wing Heritage boots can work at the office — it’s possible, folks. Good luck out there, and let me know on Twitter if these boots work out for you.

SHOP: The Red Wing Heritage Classic Chukkas via Bespoke Post