#OOTD: How to Wear a Denim Jacket This Fall

If the throes of summer strike you as a more fitting time to wear a stylish denim jacket — namely, the rugged denim jacket from Taylor Stitch that we’ll be discussing today — then, it’s time to rethink your approach to early fall style. The best denim jacket can serve as a stylish blazer replacement or a different piece of outerwear in lieu of a leather jacket — it’s both versatile and casual, able to provide warmth in the early fall chill and still ready to be taken off at a moment’s notice if temperatures pick up unexpectedly. And with all that being said, the right accessories make all the difference. When seeking casual fall style essentials to wear to your favorite beer bar or to a tailgate or a weekend brunch, it’s best to keep it simple, stylish and rugged. Hence, you’ll notice a classic henley, plus a pair of equally classic chinos from Flint and Tinder that work any time of year — not just during early fall. Naturally, your everyday carry should stay on-point, too; that’s where the best leather watch comes into play. It’s the type of timepiece that’ll stand out at the bar and look great no matter where you take it. And again, the thing is, the best denim jacket can take you a lot of different places all season long (especially when layered up accordingly). The choice is all yours — let’s get to work.

A stylish, transitional, rugged way to wear a denim jacket — guaranteed.

  • The Denim Jacket: Taylor Stitch Long Haul Jacket in 24-Month Wash, $188 — Yes, you can indeed wear a denim jacket in a lighter wash as it gets colder — just layer this rugged denim jacket from Taylor Stitch accordingly.
  • The Henley: Flint and Tinder Heavy Slub Henley, $58 — Seeing as it’s fall and all, well, we’re here to tell you that you need a seriously classic henley. It’s the perfect pairing with your rugged denim jacket, namely.
  • The Chinos: Flint and Tinder Cool Chinos, $98 — Those classic chinos you wore all summer long can still work as we move through September — Flint and Tinder gets it right.
  • The Boots: Yogi Lucas Leather Moccasin Boots, $199 — You could easiy accessorize this outfit with any one of your favorite pairs of leather boots, but these rugged leather moc boots are the way to go.
  • The Watch: Zodiac Grandville Watch, $495 — The best leather watch to complement this outfit? It might just be the rugged Zodiac Grandville Watch, mixing in a bit of dressy style and rugged functionality.
  • The Grooming Essential: HaloSmile Whitening Kit, $59.99 — For as much attention as you put into things like classic chinos, well, your smile also deserves some upkeep. This handy teeth whitening kit is but one step to keeping your smile sharp, folks.
  • The Leather Wallet: Filson Bi-Fold Wallet, $100.98 — This rugged leather wallet from Filson is assuredly one you’ll use everyday — keep an eye on it, and you’ll have it for years to come.
  • The Everyday Bag: WP Standard Canvas Travel Bag, $298 — No matter what the day throws at you, it behooves you to haul around the best everyday bag you can get your hands on; we’ve featured this handsome WP Standard Canvas Travel Bag before, and it’s every bit as essential now.

As we often say here on the blog, it’s all about picking the right pieces around which to build an outfit, especially as temperatures grow chilly (slowly but surely) this fall. And crucially, a rugged denim jacket from Taylor Stitch is going to be the great equalizer when it comes to a versatile, casually rugged piece of outerwear this season. When you match it up with rugged leather moc boots and classic chinos, the major building blocks of your outfit are in place. This is an outfit that exudes casual cool without overdoing it — hence the inclusion of a laidback-yet-timeless Flint and Tinder henley. Taken all at once, this is the type of outfit that’s going to more than serve you well when it comes time to head out on a casual weekend coffee date or to grab your favorite craft beer (both pursuits I plan on indulging quite a bit this fall!). Of course, the small details also help set your #OOTD apart, so don’t leave behind your rugged leather wallet or that critically important, best everyday bag. Finish it all off with a winning smile via the HaloSmile kit, and you’ll both look AND feel your best. It’s as simple as that. Well, not quite. But you get the picture. Enjoy the imminent start of fall, my friends!

#OOTD: How to Style a Denim Jacket This Winter

When you think of winter style essentials, your mind probably doesn’t jump to a denim jacket … does it? After all, the denim jacket is a layering essential that’s ready for spring, summer and fall, but not winter. Right? Wrong. When worn the right way, a denim jacket can absolutely work in winter. Maybe not during a blizzard or as you dress for the polar vortex, but on a day with temperatures above freezing? The denim jacket can work wonders, folks — today’s #OOTD is going to show you how. It’s all about accessorizing accordingly, reaching for warm winter essentials like an American-made cashmere scarf and prepping accordingly with a stylish casual leather watch. We’re building it from the ground up with essentials like a rugged henley, slim stretch chinos and tough shearling-lined boots, for starters. And the rest of the picks? Well, you’ll just have to read up below. Let me know if this is a #OOTD you’ll be breaking out over these next couple weeks — good luck out there!

Pairing a denim jacket with a rugged henley is an A-plus style move, folks.

The Denim Jacket: Todd Snyder Made in Los Angeles Denim Jacket, $298 — Leave it to Todd Snyder to make a simply outstanding, well-cut, well-crafted denim jacket — ideal for layering up.

The Henley: Taylor Stitch Heavy Bag Henley in Natural, $68 — Taylor Stitch has the perfect winter henley for you, made from sustainable, durable fabric.

The Scarf: American Trench Cashmere Scarf in Charcoal, $180 — Because we’re still taking on winter weather, the handsome American Trench Cashmere Scarf is the one to buy now.

The Chinos: Grayers Newport Stretch Modern Fit Chinos, $98Slim tan chinos — especially the Grayers Newport Stretch Modern Fit Chinos — add a bit of casual refinement to this look.

The Boots: Rancourt & Co. Shearling-Lined Dresden Boots, $365 —  Want stylish winter boots that are going to work twice as hard to keep your feet warm? The Rancourt & Co. Shearling-Lined Dresden Boots are that pair precisely.

The Watch: Szanto Vintage Dive Watch 5205, $224.98 — Remarkably rugged, well-made and casually stylish, the Szanto Vintage Dive Watch nicely offsets your tough denim jacket and classic henley.

The Socks: CHUP Dia Socks, $35 — This outfit balances classic neutrals with rich texture — so, the CHUP Dia Socks add some nice pattern, comfort and style. Bingo!

The Beanie: Topo Designs Merino Wool Beanie, $45 — What’s the perfect capper to this outfit? The warm, stylish Topo Designs Merino Wool Beanie.

See, doesn’t it make more sense that a denim jacket can work in the winter? It’s all about what you pair it with — the rich, deep indigo of Todd Snyder’s made-in-America denim jacket pairs right up with the perfect winter henley
from Taylor Stitch, which in turn nicely offsets the Grayers Newport Stretch Modern Fit Chinos — is there a combo more classic than that? Hardly. Accessories like the crucial Topo Designs Merino Wool Beanie and the well-made (but admittedly pricey) American Trench Cashmere Scarf are going to help you fight the chill accordingly. On the footwear front, it’s hard to go wrong with a rugged pair of winter boots, especially the remarkably tough Rancourt & Co. Shearling-Lined Dresden Boots. Stylish socks are a must no matter the season, and the warm, visually interesting CHUP Dia Socks add just enough color and pattern to this outfit. Of course, a rugged casual watch is just what you need to bring it all home — the Szanto Vintage Dive Watch was practically made for pairing with an outfit like this one. So, what say you? Will you throw on this ensemble for winter in the weeks ahead? Let me know via The Style Guide Facebook page.

Style Pick of the Week: Levi’s Trucker Jacket

Pairing the Levi’s Trucker Jacket in Spire with seasonal essentials. Short-sleeve Henley by Abercrombie & Fitch. 505C Denim by Levi’s. Expedition Watch by Timex. Buxton Boots by G.H. Bass. Glasses by Frameri.

Welcome to Saturday, folks! We’ll tell you all about the classic Levi’s Trucker Jacket today — kick back, relax and enjoy. After all, there’s no question that it’s among the best denim jackets for guys (at least in my humble opinion). Yes indeed, as the weather continues to warm up — with the occasional burst of breezy rain — I’d say there’s no more essential piece of stylish spring outerwear  you need more in your life than a rugged denim jacket. Why’s that? Well, bear with me here. We talked a few weeks ago about the need for hard-wearing transitional outerwear for spring — be it an edgy leather jacket or a on-trend bomber jacket — and the denim jacket just might be the new style you need to try. Especially when you pick one up from a well-respected brand like Levi’s, you’re getting a relatively affordable price, great fit and terrific quality. And with its use of lightweight cotton denim, the Trucker Jacket at once comfortable and yet substantial enough to keep you warm on a breezy spring night or on a spring road trip. As seen here, it works on a cloudy day with an Abercrombie & Fitch henley, slim Levi’s denim and tough G.H. Bass leather boots — that’s just for starters. And the great thing about a classic silhouette is the plethora of options you get from a brand like Levi’s.

Not into a faded denim jacket? Pick up an inky blue trucker jacket and break it in yourself. Want to channel a bit of a rock n’roll edge? A light wash denim jacket (like the “Spire” wash seen here) could be the way to go. And like other classic spring style essentials – a short-sleeve chambray shirt, a marled henley or leather loafers   — it can be mixed and matched almost effortlessly (yes, even with jeans).

Beckett Simonon

Yet another way to wear a denim jacket for spring. Trucker Jacket by Levi’s. Jack in Indigo Star Shirt by Taylor Stitch. Henley by Pistol Lake. Roma Messenger by Brothers Leather Supply. Military Watch by Timex + Todd Snyder. Explorer’s Cap by Huckberry. Glasses by Frameri

The trick when it comes to dipping your toes into the denim jacket pool? Focusing first on fit – you should be looking for a trim fit through the shoulders and arms, with a fit that hits right above or at your belt line. It’s a different silhouette for those of us who might be more used to wearing something like a slim field jacket through the spring months, but that’s all the more reason to pick up – and wear – a stylish denim jacket this season. And when it comes to pairing it with other types of denim, focus on differentiating those washes – for example, a light wash denim jacket works with everything from slim black denim to dark denim. Huckberry

A word to the wise: Only fellas like the legendary Julian Casablancas can reliably pull off wearing two shades of light wash denim. But, hey … maybe someday. Someday … (see what I did there?). At any rate, a denim jacket in either a light or dark wash also works with seasonal essentials like slim stone chinos and suede Chelsea boots, and can even serve as a reliable blazer replacement. Oh, and another handy tip – in the right fit, you can layer up your denim jacket under a piece like an olive green field jacket for style that’s designed to beat the weather and look great. So, if you don’t yet have a denim jacket … hopefully, this is a helpful starting point. If you need inspiration on how to wear a denim jacket, follow yours truly on Instagram and check out The Style Guide in the coming weeks for a new #OOTD entry. Cheers!