#OOTD: How to Dress Down a Blazer This Winter

We’ve talked in the past here on The Style Guide about how to dress for the office, but we’re now taking that a step further today — how to dress down your blazer the right way. The move here involves dressing it down for a nice blend of workwear-inspired, ruggedly casual office style. It’s a tricky balance to get right, but I think you’ll find the below #OOTD gets the job done just fine (pun intended). The trick comes in the blazer you pick, and the supporting cast with which you surround yourself. In this case, the blazer in question is the unstructured, laidback-yet-polished Outerknown Ambassador Blazer — but more on that in a second.

In other matters, the rest of these men’s style essentials might look more like pieces you wear on the weekend: Consider a rugged Taylor Stitch henley and the durable-as-heck Flint and Tinder Mill Pants to now be stylish and essential enough to wear to the office. The key, again, comes with blending it all together in a way that’s polished and cool — not stuffy. So, you’ll also find a stylish leather watch and grooming essentials from Duke Cannon in the mix. It can be a bit uncomfortable at first to mix and match pieces that you normally feel might not work together, but when you put your mind to it … it all falls into place. See for yourself below, then check out my #OOTD rotation over on Instagram.

Can you dress down a blazer? Yes, with this #OOTD … you sure can.

  • The Blazer: Outerknown Ambassador Blazer, $325 — When wearing a blazer more casually (like with a stylish henley), reach for one that’s unstructured and easygoing — Outerknown has just the ticket. (While we’re at it, head here to get a discount on Outerknown).
  • The Henley: Taylor Stitch Heavy Bag Henley in Natural, $68 — If ever there was a henley to wear with a blazer, it’d be this rugged Taylor Stitch henley. Right?
  • The Pants: Flint and Tinder Mill Pants, $98 — Mixing workwear with more dressy style staples can be a bit of a daring move, but the rugged Flint and Tinder Mill Pants balance out the two nicely.
  • The Jacket: Taylor Stitch Winslow Parka, $238.98 — You’re still going to need one of the best men’s winter jackets for a little while longer — Taylor Stitch strikes again here, helping you get to the office and stay dry while doing it.
  • The Boots: Allen Edmonds Normandy Captoe Boots, $295 — Rugged leather lace-up boots are the go-to move here, particularly as you fight the elements in business casual style.
  • The Stylish Leather Watch: Martenero Ace Watch, $595 — This handsome leather watch is bold enough for the weekend & subtly stylish enough for the office.
  • The Grooming Essential: Duke Cannon Bourbon Solid Cologne, $25 — Try something new on for size — this refined cologne from Duke Cannon is truly like no other, and that’s why I love it.
  • The Everyday Carry Essential: This Is Ground Mod 5 Organizer, $385 — The right way to organize your daily work must-haves? This Is Ground, of course. Stylish AND sleek.

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So, we’re calling this meeting to a close today in terms of how to dress down your blazer — did this #OOTD get you thinking outside of the box a little bit? Again, it all comes down to making sure your blazer (in this case, the Outerknown Ambassador Blazer) is laidback and stylish enough to wear with pieces like a rugged Taylor Stitch henley and of course, the workwear-inspired Flint and Tinder Mill Pants. You get more assistance at bridging the gap between the rugged and the office-ready with the suitably tough-yet-classic Allen Edmonds Normandy Captoe Boots (a personal favorite as seen on GearMoose!). The other accessories do the heavy lifting here, too. That includes the exceptional Martenero Ace Watch (possibly the best leather watch to buy now), plus the essential Duke Cannon Solid Cologne. Both of those bring this ensemble right to the office. And for when the weather gets to be too rough? The durable Taylor Stitch Winslow Parka helps you stay dry in style. Every single base is covered, from what to wear on your commute to what to wear at the office — casually, of course.  Again, check out my Instagram to see how I’m dressing for the office on the daily. Thanks for reading!


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