#OOTD: How to Wear a Bomber Jacket This Winter

It’s with one of the best men’s bomber jackets at the forefront that we’ll kick off today’s #OOTD, and not a moment too soon for the demands of winter weather and winter layering. In fact, the Bonobos Quilted Bomber Jacket shown below checks all the right boxes interms of versatility, wearability and warmth, and it’s exactly the kind of jacket you might not have known you needed this winter. We’ve talked about how to wear a bomber jacket for fall, to be sure, but this look updates things for winter just enough. Even with such a stylish and versatile jacket like this one, the supporting cast is still crucial, and that’s why you’ll see timeless picks like a classic chambray shirt and a rugged merino sweater, all the better for blending winter warmth with comfort and style.

As you’ll soon see, this is a go-anywhere #OOTD that you can mix and match at will — switch out the jacket and wear the sweater atop the chambray shirt on its own, or lose the sweater and wear the Bonobos Quilted Bomber Jacket atop your classic chambray shirt. With men’s performance pants offering up plenty of stretch, and with rugged leather boots along for the ride, consider this look one you can wear to the office or on the road with ease. It’s all yours for the taking, so layer up in style with my guide on how to wear a bomber jacket this season.

It all starts with a rugged-yet-classic bomber jacket and the proper menswear picks for winter alongside it.

  • The Bomber Jacket: Bonobos Quilted Bomber Jacket, $148 — This quilted bomber jacket is rugged and yet easily wearable with business casual style staples, and the quilted construction should keep you plenty warm.
  • The Sweater: Todd Snyder Italian Merino Waffle Crew Sweater, $198 — Choose carefully when it comes to layering with one of the best men’s sweaters out there, an expertly crafted piece to wear all season long.
  • The Shirt: Proof Strong Shirt, $128 — This rugged, classic chambray shirt is the kind you’ll want to wear as often as possible, and it plays quite well off your Todd Snyder merino sweater.
  • The Pants: Western Rise Evolution Pants, $149 — For the guy who values comfort and style on the go, it’s hard to top these water and stain-resistant travel pants from Western Rise, made with stretch fabric and featuring plenty of durability.
  • The Boots: FRYE Murray Chukka Boots, $298 — Keep the classic vibes going with these rugged leather chukka boots that you can wear with anything (but especially your Western Rise pants).
  • The Watch: Centric Instruments Lightwell Field Watch Mark III, $200 — This crisp, clean, classic leather watch is both dressy and casual at the same time, making it ideal to wear alongside your Bonobos bomber jacket.
  • The Belt: Billykirk No. 288 Center Bar Belt, $99 — Make sure your accessories are on-point with one of the best leather belts for men, the perfect way to round out this ensemble.
  • The Grooming Essentials: Huron Starter Kit, $20 — Score an easy-to-use trio of the best men’s grooming picks for a new year, and keep your face and skin in fine form despite challenging winter weather. Better still, you can subscribe to the brand to get deliveries as often as you like.

Part tailored jacket, part sweater, all versatility.

For essential winter style and warmth, it really is all about getting the details right, and that’s particularly true when it comes to how to wear a bomber jacket for men this winter. Of course, the Bonobos Quilted Bomber Jacket is quite the way to kick off an #OOTD, what with its tough quilted construction and casual styling potential. On top of that, it’s highly versatile — witness the fact that you can layer a Todd Snyder merino sweater atop a classic chambray shirt for the kind of ensemble that works on the office, out on the road or layered up to enjoy a beer at an outdoor beer garden. To really drive home the “wear anywhere” nature of this look and the Bonobos Quilted Bomber Jacketa pair of men’s performance pants toe the line between road-ready and office-friendly.

The same can be said for your rugged leather chukka boots, all the better to get around with style and dependable good looks in mind. Close things out the proper way with the right accessories, including a classic leather watch for sharp, easily wearable style. Naturally, one of the best leather belts for men helps finish off this outfit quite nicely, and a the best men’s grooming picks makes it easy to keep your skin in great shape this winter. Put all the pieces together properly, layer up in style and get out there this winter. And if you really like this look and want to talk more menswear, head to Twitter and give me a follow.


#OOTD: How to Wear a Bomber Jacket This Season

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.

Ahh, yes. The classic bomber jacket. A men’s style staple that’s experienced a huge resurgence in recent years, in part thanks to certain, ahem, celebrities (Mr. Kanye West among them). But how do you take a style that’s seen on the runways and boil it down to an essential, easily wearable outfit? A solid menswear #OOTD, if you will? That’s why we’re here today at The Style Guide, and after you read the below, your questions will all be answered (hopefully). The key with looking at a major trend sometimes isn’t too follow it exactly — that is to say, you can buy that Alpha Industries bomber jacket, but maybe (no, definitely) switch it up from how Yeezy wears it. In this case, we’re working with a different bomber jacket entirely, and classic style staples like a slim chambray shirt and … well, we’ll leave that to the imagination for now. Have thoughts or suggestions on how you would style your bomber jacket? Leave a comment below or join the (very fun!) conversation on Twitter.

Slick, sharp and casual -- just the right way to wear a bomber this fall.

Slick, sharp and casual — just the right way to wear a bomber this fall.

The Bomber Jacket: Bridge & Burn Northrup Olive Jacket, $218 — See, I said we were using a different bomber jacket entirely — right? The olive color is neutral and yet still a change of pace from navy or that military green typically seen on bomber jackets, and the front snap hip pockets and stand-up collar are neat design touches, too.

The Chambray Shirt: JackThreads Chambray Workshirt, $49 — The great thing about starting an outfit with a neutral bomber jacket is that any classic chambray shirt in your arsenal would work — yet this neat patterned workshirt offers a heftier weight for fall, plus a pattern that’s just different enough.

The Denim: Mott & Bow Slim Morton Denim, $128 — You (probably) should recognize the Mott & Bow Slim Morton as a recent Style Pick of the Week entry, and it’s a good pick here because of the super-comfortable four-way stretch and dark black color in a no-fade rinse.

The Sneakers: UGG Kramer Sneakers, $120 — Your humble author discovered the comfort and style of UGG men’s sneakers during a summer trip to Michigan, and the Kramer falls right in line with those same qualities. Surprised? Don’t be — these are a reliable, stylish high-top sneaker pick for the season ahead.

The Socks: ICNY Half-Calf Gradient Socks, $13.98 — Sometimes, you just need simple, straightforward socks that offer neutral color, comfort and performance. You get all that with this pair for a pretty decent price, and the fact that the fine folks at Huckberry sell ’em is a positive.

The Watch: MVMT Watches The 40 in Rose Gold/Natural Leather, $120 — Since when can you get a crisp, versatile watch fit for both casual and dress situation? At a low price, to boot? Since MVMT Watches started making ’em, that’s when. The case diameter is just right, and the look is crisp and clean for just over $100.

The Belt: Tanner Goods Classic Belt in Hickory, $99.98 — Looking for an investment-worthy belt that’ll break in beautifully and offer a rich accent to dressy and casual outfits? Here it is.

The Everyday Carry: Bull & Stash The Stash Notebook (5.5″ x 9″), $50 — $50? For a notebook? Bear with me. Bull & Stash Notebooks support American-made production and top-notch quality, and they’re refillable — just swap out the paper when you’re done (save those memories though).

Buck Mason - Timeless Design. Made in America.

If the below #OOTD feels a bit too casual for you with those sneakers, swap them out for a pair of stylish men’s dress shoes (casual wingtips are a nice way to go), or heck, keep the sneakers and add a navy knit tie to wear this to the office. This sort of casual yet put-together look might be best for a  weekend coffee run or, dare I say it … Sunday brunch. And since it’s a midweight approach to wearing a bomber jacket — note the lack of a heavy hoodie, a la Kanye — it should work in the early fall or spring in the right conditions. For a bomber jacket that’s certainly an investment, it’s a positive that it can be worn multiple ways. For a look at how yours truly styles spring and fall outerwear for similar situations, head over to Instagram — maybe? Please?

‘Til the next #OOTD,