#OOTD: The Best Way to Wear a Flannel Shirt This Fall

Gather ’round, Style Guide readers — today’s #OOTD tackles a favorite topic when it comes to rugged men’s fall style: How to wear a flannel shirt this season. If flannel shirts call to mind the mid-aughts boom of American workwear, well, they should — they were a key piece of #menswear then, and the right flannel shirt is just as relevant now. Today’s shirt of choice, the Filson Vintage Flannel Shirt, channels just the vibe you want when wearing a flannel shirt. It’s got all the trappings of a classic piece, but it’s just a bit more modern. With a cool black-and-cream color, it’s less outdoors-y and instead, just … ¬†a cool shirt. And the way you wear your new favorite flannel shirt is going to make all the difference, too. Pair it with rugged style essentials like a premium¬†slim henley and textured Bedford cord pants, and you’re going to shake off all those “urban lumberjack” connotations. Fear not, though — we’re still finishing off this #OOTD with rugged leather boots. ¬†I know this much: You can make this outfit work for you at a football tailgate, at a bonfire or on a brewery tour — and that’s just the tip of the iceberg. Let me know your thoughts over on Twitter when you get the chance, if you so please.

Best men's flannel shirts

Think again about how you wear your flannel shirt — this Filson shirt bucks the trend and looks great.

The Flannel Shirt:¬†Filson Vintage Flannel Work Shirt in Black and Cream,¬†$145¬†— The centerpiece of many a stylish and rugged fall outfit, Filson gets the color and classic fabrication just right with its Vintage Flannel Work Shirt.

The Henley:¬†Billy Reid Speckled Henley,¬†$155.98 — ¬†Yet another critical fall layer, this made-in-Italy Billy Reid henley is a premium upgrade over a standard thermal henley — perfect for layering with a Filson flannel.

The Pants:¬†BANKS Roll Bedford Cord Jean,¬†$75¬†— Rather than reaching for dark blue denim, reach for the slim, fall-ready BANKS Bedford Cord Jean — textured, unique and slim-fitting.

The Boots:¬†Wolverine Original 1000 Mile Boots in Roughout, $299.98 (When On-Sale) — For fall, Wolverine has taken its 1000 Mile Boots and upgraded them in a rich, seasonally ready roughout leather. Perfect.
The Belt:¬†Sturdy Brothers Everyday Belt in Chestnut,¬†$80¬†— To stand up to your sturdy leather boots and a rugged flannel shirt, a tough leather belt from Sturdy Brothers is just what the doctor ordered.
The Watch: Pantor Sea Lion Watch, $424.98— This outfit is packed with fall-ready neutrals, so shake up your wrist game with the striking, durable Pantor Sea Lion Watch. It’s the ideal, rugged watch to wear to a football game or a bar crawl.
The Bag:¬†Topo Designs Mountain Briefcase, $119.98 — Whether you head to a house party or out on a day trip, the sturdy, well-made Topo Designs Mountain Briefcase is more casual (and durable) than the briefcase moniker implies.
The Beard Balm:¬†Upstate Stock Willowemoc Beard Balm, $22 Upstate Stock happens to be one of my favorite spots for menswear in Brooklyn — and they make a nice beard balm to tame your mane this season.
Are you sold yet on the versatile, rugged styling potential of the¬† Vintage Flannel Work Shirt¬†from Filson? In a cool color scheme, it’ll work as a warm top layer over something as premium and understated as the Billy Reid Speckled Henley. And when you team up that combo with a crisp set of trousers like the BANKS Roll Bedford Cords, you’re set for casual fall excursions from the city to the country and back. Don’t step foot outside this fall without tough leather boots, either — I’d strongly urge you to invest in the stellar Wolverine 1000 Mile Boots — are you with me there? A durable, weather-ready watch like the¬†Pantor Sea Lion Watch¬†is going to fit right in with the tough nature of this outfit, and the¬†Topo Designs Mountain Briefcase¬†is standing at the ready if you need a new fall go-to to haul your everyday carry. So, I think we’re all set with today’s #OOTD. Thanks, as always, for reading!
-Beau

#OOTD: How to Wear a Flannel Shirt for Fall

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

It’s been a few weeks since we had a proper #OOTD here on The Style Guide, so we’re getting back to business today. As fall weather rolls into your neck of the woods, perhaps you’ve been breaking out some of your favorite style essentials for the season. It’s a time much-loved around Style Guide HQ for that very reason — and your list of seasonal essentials should definitely include a flannel shirt. Now, cotton flannel fabric in a plaid pattern carries with it a bit of a negative stigma — it was¬†such a trendy staple for years that it might seem played out. But there are a few key ways you can break out a flannel shirt without looking as if you’re heading off to chop wood. The key starts, as always, with the fit of your shirt. Take that classic flannel fabric, slim it down (or size down) and pair it with a decidedly modern bomber jacket. Oh, that’s right — that’s what the below #OOTD is doing. Take a look below, follow your author on Instagram and follow The Style Guide on Facebook for your daily prescribed dose of #menswear.

Not too trendy, not too boring -- just right. A modern flannel shirt paired with other modern staples.

Not too trendy, not too boring — just right. A modern flannel shirt paired with other modern staples.

The Flannel Shirt: Eddie Bauer Favorite Flannel Shirt,¬†$49.99 — There are some brands you don’t mess with when it comes to flannel. Eddie Bauer’s been making these for years, and they’re comfortable, easily wearable and — here’s the key — slightly visually different in an engaging Baltic plaid pattern. Size down for a slightly trimmer fit, and wear it a ton.

The Bomber Jacket: Beckett Simonon Cole Bomber Jacket, $295 — The biggest key to making this look more modern than lumberjack? A beautiful calfskin suede bomber jacket in a trim fit. Treat this piece with care (I.e. Avoid the rain) and it should last through many seasons to come.

The Denim: Cheap Monday Sonic Denim (Available via East Dane), $90 — Learn more about a denim brand that could be a new favorite — we’re talking classic washes, nice fits and agreeable price points for the quality.

The Boots: Chippewa Original 6-Inch Service Boot in Cordovan, $269.98 — Does it get any better than ridiculously durable Chippewa boots, especially in Cordovan? Hardly. These boots¬†are the rugged complement to the slick bomber jacket — you’re wearing a flannel shirt, after all.

The Socks: American Trench Pima Cotton Houndstooth Socks, $18.98 — Textured socks in this particular color should play nicely off the deeper blue of the plaid flannel shirt — the American-made quality doesn’t hurt, either.

The Watch: Timex for J. Crew Andros Watch, $118 — J. Crew does many things quite well, and a few things very well — its collaborations with third-party partners rank high on that list.

The Belt: Rag & Bone Rugged Brass Belt. $150 (Available via East Dane) — Is $150 a lot for a belt? It certainly is. But Rag & Bone does essential basics without fuss — this durable belt falls within that category neatly.

The Everyday Carry: Taylor Stitch Raw Brass Keyhook, $32 — Goods from Taylor Stitch — from the brand’s Everyday Chambray Shirt to this keyhook — are as well-made as can be. Carry this thing everywhere, and never lose your keys again, yeah?

Again, the key with breaking out a flannel shirt revolves around picking a more unique color than the tried-and-true red-and-black combination, along with a slimmer fit. Of course, a sharp suede bomber jacket helps matters out, as do simple, clean accessories like a NATO strap watch and premium socks (yes, the socks do make a difference). Some of the picks are definitely pricey, but as we always say, they can serve as a nice reward, and a reminder of the quality you get when you pay a bit (or a lot) extra for everyday goods. Got any questions on this #OOTD? Or would you swap in a few different brands? Hit me up on Twitter.
Check back tomorrow for another fall-centric style suggestion — and until then…
Stay stylish,
-Beau