#OOTD: How to Wear Chelsea Boots for Fall and Winter Weather

Ahh, yes — we’re back for another #OOTD here on The Style Guide, and here’s the even better news: We’re really digging into tailored menswear for colder weather. You’re going to love it, or your money back. Stylish men’s Chelsea boots are an essential that shouldn’t be slept on, even if you haven’t yet shopped around for the perfect pair yet.¬† They’re a style of shoe that’s at once sleek and refined, yet edgy — there’s a reason rock stars love these boots. Now, we’ve previously talked the best pair of Chelsea boots to buy for fall, and we’re upping the ante a bit here today. The Hudson Shoes Wynford Chelsea Boots are just the ticket, and they’re potentially among the best men’s Chelsea boots. Specifically, we’re looking at how you can wear your new favorite Chelsea boots with a bit of tailored edge. So, think a stylish cardigan, slim wool trousers¬†and of course,¬† a classic dress watch. You’re going to recognize plenty of other winter style essentials in this #menswear look, too — from an American-made cashmere scarf to surprisingly stylish men’s socks. If that all sounds great to you, then read on. Let me know your feedback in the comments, and I’m always up to chat on Twitter! Talk soon.

Sleek Chelsea boots done up in refined, sharp fashion. Perfect for fall and winter, no?

The Chelsea Boots: Hudson Shoes Wynford Chelsea Boots, $230¬†— Here’s the centerpiece of this outfit — a pair of stylish, sleek Chelsea boots. Crafted from rich, dark brown leather and featuring no-frills styling potential, the Wynford Chelsea Boots from Hudson Shoes couldn’t have come into your wardrobe at a better time.

The Cardigan:¬†Mollusk Surf Shop Jeffrey Sweater in Cloud Grey, $180 — What better way to offset a pair of refined Chelsea boots than with a slightly rugged, stylish shawl collar cardigan? This is the kind of classic cardigan that a fella like James Bond might wear.

The Shirt: Corridor NYC Check Flannel Shirt, $159.98 — Quite simply, Corridor NYC makes astonishingly beautiful, classic shirting right here in NYC — the Check Flannel Shirt is a nicely tailored, dressy complement to this ensemble (and it features a winter-friendly wool blend).

The Trousers: Taylor Stitch Telegraph Trousers in Navy Donegal, $178¬†— While you can really wear your favorite Chelsea boots any way you want, slim wool trousers — especially the handsome Telegraph Trousers from Taylor Stitch — are a perfectly tailored move.

The Scarf:¬†American Trench Cashmere Scarf in Red Flecked, $180 — Although you could certainly throw on a slim topcoat to finish off this outfit, a cashmere scarf from American Trench is a cool way to layer up in style while adding visual interest to a classic shawl collar cardigan.

The Socks:¬†Anonymousism Boucle Mix Socks, $18 — As I always say here on this blog, don’t sleep on stylish accessories — particularly well-made socks from Anonymousism. Simply designed, well-made and stylish, the Boucle Mix Socks are a refined finishing touch.

The Watch:¬†About Vintage 1815 Chronograph, $349¬†— What’s the one small accessory — besides stylish socks — that can both define an outfit and add quite a lot of style to said outfit? A classic men’s dress watch. This vintage-style About Vintage Chronograph is sharp and refined.

The Belt: Tanner Goods Standard Belt, $104.98¬†— Last but not least, we can’t forget a simply designed, durable men’s belt — especially not the excellent Standard Belt from Tanner Goods.

That’ll about do it for this tailored men’s style ensemble — do you have a better idea of how to wear Chelsea boots this season? The¬†Wynford Chelsea Boots from Hudson Shoes are an excellent starting point for a sleek and tailored #OOTD — at least, that’s what I think. This look gets even sharper when you throw in winter-ready, dressy staples — take the¬†Telegraph Trousers from Taylor Stitch, for instance. And similarly weather-ready shirting, like the Corridor NYC Check Flannel Shirt, also helps you get the job done in terms of seasonal dressing.¬† Lest we forget, a¬†classic cardigan is going to act as a reliable stand-in for a classic blazer. That combo will be all the warmer with an¬†American-made cashmere scarf and stylish Anonymousism socks, too. Of course, you can’t leave a stylish dress watch off your wrist, and that’s where the terrific¬†About Vintage Chronograph is going to help you stay on time in style. What’s your take on this #OOTD? Will the¬†Wynford Chelsea Boots from Hudson Shoes be finding their way onto your feet this season? Let me know in the comments!

Thanks for reading,


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