#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.

Shop Faherty Brand

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!


Shop Faherty Brand

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#OOTD: How to Dress Down a Summer Blazer

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.

As we’ve talked about in past #OOTD entries here on The Style Guide, summer style — particularly at this point in the season — can be a bit tricky. Perhaps you feel you’ve exhausted all the ways to wear shorts in the summer that you can think of, or maybe you’ve even tired of styling linen pants in the heat. But, that’s where summer also works out well. Since it’s warm, you get a bit of leeway when dressing. And that means you can put together stylish combinations that are also unexpected. Those khaki suit trousers? Break them up from the rest of your suit. Throw in style staples that should already be in rotation — like a classic navy blazer — and you’re set with an #OOTD that works for traveling in warm weather¬†or waltzing to Sunday brunch. Oh, and a great polo is also a must-have. But where to get all this great gear? Look no further than the below ensemble — and follow along on Instagram to get more daily styling tips (if you feel so inclined, that is).

Mashing up your favorite style essentials, from a crisp summer polo to a classic blazer and comfortable slip-on sneakers.

Mashing up your favorite style essentials, from a crisp summer polo to a classic blazer and comfortable slip-on sneakers.

The Polo: Mack Weldon Vesper Polo, $68 — Yes, it’s true: The brand that makes your favorite long-sleeve merino tee is here with a new polo that’s crisp, well-tailored and made from very breathable micro-mesh knit fabric.

The Blazer: Grayers Cayman Blazer, $104.98 — At just more than $100, this blazer is a heck of a deal, made from 100 percent cotton and featuring Bemberg-lined sleeves (that’s the good stuff, FYI).

The Pants: Canvas by Lands’ End Stretch Chino Suit Trousers, $89 — Just when you thought you could only wear suit pants with a suit, along come these versatile chino trousers cut with a hint of stretch.

The Pocket Square: Ties.com White Edged Linen Pocket Square, $10 — A sharp navy blazer deserves a crisp white pocket square cut in a summer-appropriate weight, and at $10, this thing’s a steal.

The Sneakers: SeaVees Hawthorne Slip-on Standard in True Navy, $78 — A pair of classic white sneakers would also work here, but the navy plays nicely off the powder blue polo.

The Socks: Sock Genius Villa Park No-show Stripe Sock, $10 — The same spot you hit up to snag that pocket square can also hook you up with comfortable, stylish no-show socks for a¬†nice deal.

The Watch: Armogan Spirit of St. Louis Chronograph, $225 — A sporty-yet-stylish polo calls for a¬† slick watch inspired by the world of aviation, and the navy blue strap plays handsomely off the crisp white dial.

The Sunglasses: Sunski Madronas Sunglasses, $39.98 — Simple is sometimes better when it comes to great style, and that’s the case with these durable and very¬†affordably priced shades via Huckberry.
Buck Mason - Timeless Design. Made in America.
Putting together an outfit when you’ve been dressing for the warm weather for a few months needn’t be all that difficult, even if at first it sounds¬†taxing¬†— especially when you’ve got pieces that combine subtle style efficiently. The base of the outfit is the same thing you might wear on the weekend — stylish slip-on sneakers — yet the other pieces, like the sharp polo and the navy blazer, are more suited to the work week. Yet in tandem, the combination works because the colors play well off each other and the overall ensemble — slightly sporty yet stylish — is very well-suited to summer. It’s going to be hot, and a breathable polo and cotton blazer work well together. Chime in with an #OOTD suggestion of your own at The Style Guide Facebook page in the meantime.

Do you own a new Mack Weldon polo yet? Would you style it with a navy blazer, or ditch the jacket and keep it casual?

#OOTD: How to Dress Down a Wool Blazer

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 series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

With winter weather still in full force for a lot of us, there can be a tendency to get into a bit of a style rut. That is, there are only so many ways you can style a shawl-collar cardigan or a crewneck sweater ¬†before you want to change things up a bit. The good news is that, for so many of us, high-low dressing (that is, mixing and matching casual and formal pieces) is easier to do than ever before, regardless of what you might find yourself doing day-to-day. The below outfit makes use of some staples you likely already have in your closet (like dark denim, for starters) and puts ’em together in a slightly unexpected way. As a matter of fact, you might recognize the blazer from last week’s #OOTD post.¬†Get the lowdown here, and then get those goods in your shopping cart.

Putting it all together -- combining style essentials you might already have in your closet.

Putting it all together — combining style essentials you might already have in your closet.

The Blazer: Frank & Oak Fairmount Deconstructed Blazer in Light Brown, $145 –A slim, soft sportcoat with a tailored fit and minimal padding — ideal for casual wear.

The Henley: JackThreads Daily Henley in Indigo, $34 — A great price for a superb piece that’ll age well over time; the “dressed-down” part of this outfit.

The Denim: Mott & Bow Skinny Mosco Denim, $96 — A classic pair of denim with great color and a nice bit of stretch (full review here). Note that Slim and Straight options are also available.

The Shoes: Frank & Oak Modern Leather Brogues in Dark Tan, $175 — Italian leather and European construction takes this pair to another level, plus¬† the color stands out remarkably well against the denim. Click here for a full Frank & Oak review.

The Socks: Anonymous Ism Wave Socks, $25 — Definitely a pricey splurge, but worth it for the quality and nice color they provide.

The Watch: Timex Waterbury Watch, $80 — A new Style Guide favorite; very well-priced, clean and classic. The ideal blend of casual and classed-up style.

Oh, and seeing as it is winter and all, finish off your oufit with my picks for the best winter accessories.

So with the above outfit in mind, I’d say give it a try just as soon as you can — when you pick up style staples that fit well and can be mixed and matched with ease, you’ll give yourself plenty of #OOTD options.

Would you rock the above look? How do you dress down your blazer?