#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,


The Friday Read: Athleisure, Common Projects Chelsea Boots and the 2016 Olympics

Editor’s note: Expect these posts once a week on Fridays — consider this a jumpstart on reading for your weekend downtime. Expect a mix of style and non-style content. For more entries, click here.  

With so much going on at the (small but well-appointed) Style Guide HQ, it’s becoming tough to keep track of the days. If it’s Friday, that must mean it’s almost time to hit the road again — this Sunday, I’m heading west to Liberty Fairs in Las Vegas, before a day back in New York … and then more travel to my home state of Michigan. But first, Liberty Fairs — it’s a twice-yearly contemporary men’s trade show, and it stopped in the Big Apple about a month ago during New York Fashion Week: Men’s.  It’s another chance for retail buyers, fashion editors and writers and industry pros to get a look at what top menswear brands are slinging for the Spring 2017 season. There’s certainly a lot of hustle and bustle associated with trade shows, but ultimately, they’re about exploring new brands, analyzing key industry trends, and forging strong relationships in the menswear industry — that much I know is true, as I’ve met some great people at large, sometimes overwhelming conferences (take my buddy Jamal of StyleSocietyGuy, for instance).

Buck Mason - Timeless Design. Made in America.

With that in mind, building those relationships is my primary objective, as I’m jetting out there on behalf of Timberland to meet with media and rep the brand as part of my day job. Of course, you can expect a full #menswear blog post coming at the completion of my trip (click through here for more travel style in the meantime).  While my mind’s been fully focused on prepping for the upcoming trip, the Olympics have also captured my attention — maybe yours, too? If you’ve got an Olympics viewing party on the docket this weekend, here’s what you should wear. Or perhaps you just want to check out more of those hilarious Michael Phelps face memes? Go for it. Before you go too far down that rabbit hole, stick around here and check out the week in all things men’s style — everything from stylish boxer briefs to athleisure is up for discussion. To keep up with my travels in real-time, head to Instagram or Twitter — and click through the pieces below to start your weekend in style.

  • Now more than ever, Esquire says you should grab yourself a stylish pair of Chelsea boots — and I tend to agree! In fact, The Style Guide took a look earlier this spring at the best men’s Chelsea boots to buy now.
  • While we’re talking about  Esquire, the publication also reviewed the best boxer briefs for men — if you know me, you know I love me some Mack Weldon boxer briefs, although those didn’t make the aforementioned list.
  • We talk a lot (I mean, a LOT) about style upgrades on this blog, and sandals are one area that’s often overlooked. If that’s a part of your wardrobe you want to look a little better, the footwear purveyors at GREATS have you covered (as always). The brand’s new Amalfi Slide is a luxurious, Italian-made leather slide available in crisp white (Blanco) or black (Nero), including two versions stamped with “BKNY,” a nod to the brand’s #BornInBrooklyn roots. As crazy as it might seem to advocate for leather sandals, designs like these popped up on the runways at Todd Snyder’s New York Fashion Week: Men’s show in July 2016. Crucially, the leather quality and subtle looks mean these might not look that bad at a particularly relaxed barbeque — I’ll let y’all be the judge of that.

Looking for more style content? Look no further.

  • What’s one shirt — not chambray — that you can wear across all four seasons? The essential Oxford shirt. So, here are the 10 best Oxford shirts for men, as rounded up by yours truly at GearMoose this week.
  • Lastly, the balance between looking good at the gym and looking sloppy can be pretty small — and if you want gear that’s versatile outside of slinging weights, it’s even trickier. That’s where athleisure comes into play; the style (or trend) mixes traditional tailored silhouettes with technical fabrics, and I wrote about 5 athleisure lines to know for The Manual.

Follow along with this weekend’s explorations on Instagram, and check back Saturday for another Style Pick of the Week entry.

Buck Mason - Timeless Design. Made in America.

Online Shopping Picks: Stylish Men’s Chelsea Boots to Buy Right Now

Editor’s note: Get the scoop on all the #menswear you could ever need with all The Style Guide’s online shopping picks.

Chelsea boots via ASOS, with a bit of seasonal wear-and-tear. Learn how to style yours below, folks.

Chelsea boots via ASOS, with a bit of seasonal wear-and-tear. Learn how to style yours below, folks.

In case the headline wasn’t enough of an indicator, today we’re talking Chelsea boots on The Style Guide. Like other pieces that once seemed relatively trendy (remember when J. Crew  nearly single-handedly brought back the now-essential chambray shirt?), these guys have practically become a safe bet as far as a great footwear option for stylish guys. They’re not as hearty as a sturdy pair of winter boots, to be sure, but in the right style and color, they can definitely work in three seasons — and maybe four, if the snow holds out. The silhouette is generally sleek and sharp, and that seemingly goes for whether you pick ’em up in brown or black leather, or suede — all picks seen below. A bit of rocker edge never hurt anyone, either. And while at first it might take a while to get used to just slipping into a pair of boots — as it did for me — you might soon find they’re your go-to footwear option when you want to step away from leather sneakers, dress shoes or more military-inspired boots. Check out today’s Style Guide picks, and give us a look on Facebook for all the menswear content you can possibly ‘Like.’

#1. Thursday Boot Company Brown Duke Boot — $199

A reliable and (hopefully) hard-wearing pick from an upstart brand.

A reliable and (hopefully) hard-wearing pick from an upstart brand.

While it was an exceptionally close call between the Duke Boot and the Ellis Boot from Jack Erwin (option numero dos), a slightly lower price and more versatile brown leather swayed this writer (more readily wearable in winter, see?). Thursday Boots continues to be a solid option if you want to up your boot game for not a whole lot o’ dough, and they nearly always deliver. You get better quality than a pair of Chelsea boots from a fast retailer like H&M, yet you’re not ponying up an arm and a leg from a pricier brand. Added details like the studded rubber outsole should ensure a smooth grip no matter the season.

#2. Jack Erwin Ellis Chelsea Boot in Brown Suede — $220

Sleek and sturdy at the same time -- a nice combination.

Sleek and sturdy at the same time — a nice combination.

Perhaps it’s the thought of springtime being (hopefully) not too far off, but these beautiful Jack Erwin brown suede Chelsea boots end up near the top of this list for a few great reasons.  On the comfort end of the equation, these boots feature a rubber sole and full leather lining — both things you’ll be grateful for if you’re out and about a lot. And on the looks end of things, the suede appears rich and high-quality — take ’em for a spin with some white jeans when the time comes. Sure, they’ll require a little extra care and will probably be needed to shelved when heavy snow hits, but the rest of the time, they’re on the money.

#3. Wolverine 1883 Garrick Chelsea Boot — $175

Heritage-quality leather and rugged style details at an approachable price.

Heritage-quality leather and rugged style details at an approachable price.

As sold by East Dane, these boots are part of Wolverine’s 1883 line, which has more than a dozen individual styles on the brand’s Web site. The biggest thing to note here is that, somewhat incredulously, you’re getting the Wolverine brand name for under $200 — no small feat when you look at the brand’s 1000 Mile line (particularly the Camden Chelsea Boot). At any rate, the Garrick is a slightly more rustic-looking Chelsea boot, what with burnishing details on the toe and heel, plus that wrinkled leather. These will still do just fine with dark denim or navy chinos, and they’d even add a nice contrast to spring denim.

#4. ASOS Tan Suede Chelsea Boot — $68.43

Dark tan suede Chelsea boots that combine some unique color with a terrific price.

Dark tan suede Chelsea boots that combine some unique color with a terrific price.

Got an extra two quarters lying around? So these ASOS Chelsea boots are, it goes without saying, a downright steal for the price. And they’re another style that, like the Florsheim boots above, are a very worthy pickup if you’re looking to dip your toes into this trend. They’re cut a little lower on the heel for a slightly more continental look . Note that the suede isn’t the highest-quality, but it’s actually held up decently as part of a rotation and with less winter wear (the pair you see at the top of the page belong to yours truly — thanks Santa!).

#5. Florsheim Indie Gore Boot in Toffee — $99.90

More casual in nature thanks to the color and gore detailing.

More casual in nature thanks to the color and gore detailing.

Florsheim’s Indie Gore Boot has bit more going on visually than the typical Chelsea boot thanks to the side-gore detailing and the textured leather. Those aren’t all bad things, though. You’re getting a more casual pair of Chelsea boots — there is such a thing — for a great price. Feel free to beat these things up a bit; they’re the perfect pair to pick up if you’re just giving the silhouette a try. The Toffee color would sit nicely under some slim wool trousers now, and they’d work equally well under lightwash denim in the spring.

Putting together this list was quite tricky — it’s certainly no small feat to sort through Chelsea boot options when lauded retailers like Common Projects are throwing their (very minimal) hats in the ring. If you find yourself on an extreme budget but really want to go for the style, an option like H&M isn’t all bad for now, and more comfort-minded brands like Dr. Scholls are also producing Chelsea boots with a rugged edge. The biggest key to keep in mind is how you can make them work for you. If you find yourself wearing a lot of slim denim and mixing staples like tees with unconstructed blazers, the Chelsea boot is going to be a similarly slick style option. But if you need a more rugged pair of boots for crossing town, maybe save these guys for special occasions. Either way, it’s one footwear option I’d say you should give some thought to in the coming weeks — before everyone else beats you to the punch!

Stay stylish and happy shopping,

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