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Style October 19th, 2023

1 Piece, 5 Ways: Gray Herringbone Tweed Sport Coat

Style October 19th, 2023

How To Style A Tweed Sport Coat

There are many reasons why a gray herringbone tweed sport coat is one of the quintessential fall and winter tailored jackets. Practically, it’s durable and warm, which is a necessity once the temperatures start to drop. Aesthetically, it has an extremely classic and timeless look. And intangibly, it has a certain sort of nostalgic charm.

In addition to all those very good reasons this particular tweed sport coat is considered a classic seasonal piece, one of my favorite reasons—as regular readers of HSS will attest—is that it is incredibly versatile. I know I may sometimes sound like a broken record on this point, but I believe that building a wardrobe with intent and versatility top of mind is one of the best ways to always look good and get the most for your money.

To illustrate just how versatile a gray herringbone tweed sport coat is, here are five ways I’m wearing it this fall.


1. Casual Business

No, that’s not a typo. I titled this look “casual business” rather than “business casual” on purpose. While it most certainly could be categorized as business casual due to the sport coat and trouser combination —in fact, that’s how you’ll find it in the Style Guide—I feel like the overall gray color palette makes it more of a softer business outfit than a hardcore business casual look. Semantics, I know, but humor me.

When used in large quantities, gray can often come off as severe, or worse, bland. But I’ve taken care of that conundrum in two different ways here.

First, all of the pieces in this look have a certain softness to them. The tweed sport coat, the flannel trousers, the wool tie, and of course, the suede split toes. They all combine to add a sense of warmth to a color that can have a tendency to come off as cold or bleak. Additionally, it gives the look a more relaxed appearance.

Second, pattern and texture. As well as giving off an aura of warmth, the textures of the sport coat, trousers, and shoes also provide a degree of depth. And the tight herringbone pattern of the jacket, along with the interplay of the stripes of the tie create, a nice level of visual interest. Remember that you can always combine similar patterns so long as they are different sizes or scales.


2. Fall Prep

Since a gray herringbone tweed sport coat has some pretty serious collegiate and professorial vibes, it makes sense that it works effortlessly in a preppier context. Paired with a classic OCBD and iconic Polo Bear sweater, you’ve got a look that’s equally at home on campus or for pretty much any day of the week.

You can pop the sport coat’s collar if you want—or not. I do it from time to time. Sometimes it’s for aesthetics, and sometimes it’s practical, as it helps to keep my neck warm. Either way, if you’re going to attempt it, own it and don’t think twice.

If you’re a sport coat and jeans type of guy, there is simply no better option than a tweed sport coat for that style. Both tweed and denim are extremely rugged fabrics, which means that they pair together very easily. And the light gray color ensures that it’ll work with a wide variety of different jean washes, as you’ll see in just a bit.

3. Cocktail Hour

Easy, simple, chic. There is no better way to pull off a look like that than by pairing a turtleneck with a sport coat. I’ve always found it to be effortlessly stylish and sophisticated; working off an all-black foundation consisting of a cashmere turtleneck and flannel pants, I think, is going to be my vibe for fall evening events and holiday cocktail parties this year.

I love a gray herringbone tweed sport coat with this combination. It softens the overall look, giving it more of a relaxed feel. The light gray color provides a striking bit of contrast and focuses your attention up toward my face. And the herringbone pattern, along with the more rugged texture of the tweed fabric, provides a great deal of visual interest.

4. Three Days Of The Condor

I have a confession to make. About five or so years ago, I got really into 1970s Robert Redford. Like, really into. I mean, come on! “All The President’s Men,” “The Sting,” “The Candidate,” “The Way We Were,” “The Great Gatsby”—all great films with great style. However, my favorite 70s Redford movie is, without a doubt, Sydney Pollack’s political thriller “Three Days Of The Condor” and this look was pretty much appropriated directly from the movie.

(And if I’m being completely honest, that movie was the inspiration for adding a gray herringbone tweed sport coat to our fall and winter collection.)

For those not familiar with Condor, Redford stars as Joseph Turner, a CIA analyst who works at the American Literary Historical Society in New York City; which is actually a clandestine CIA office. Turner’s bookish leanings translate to his style in the form of collegiate meets classic American menswear.

I’m not 100-percent true to the original outfit, though, having swapped the crew neck sweater for a v-neck, hiking boots for a pair of suede chukkas, and leaving the sweater untucked. Oh, and no gloves in the right pocket

But here’s the question: Ridiculously esoteric Halloween costume? Or timeless approach to American style?


5. Layered Sweater

Same, but different. This is if Joseph Turner worked for a bank rather than the CIA. All kidding aside, what we have here is another look built around timeless menswear principles and a classic color palette. The softness of the navy cashmere v-neck pairs perfectly with the charcoal gray flannel trousers and burgundy wool tie while the OCBD plays into the sportier and preppier leanings of the tweed sport coat and oxblood loafers pull everything together.

One of the things about fall is that the temperatures can be a bit unpredictable. Maybe you thought you needed a regular coat but then it was too much. That’s where a tweed sport coat really shines as a wonderfully stylish transitional outerwear piece. Layer in a v-neck sweater for some added warmth and classic style.


The Bottom Line

A gray herringbone tweed sport coat is a practical, stylish, and versatile piece that belongs in every well-dressed man’s fall and winter wardrobe. Be sure to check it out in the He Spoke Style Shop with my suggested styling or customize to suit your own personal style.

Thanks, as always, for reading.

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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Edited by Rachel Butler

Photography by Rob McIver


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The event took place in New York City’s Chelsea neighborhood at The Groom Shop’s exquisite showroom, which draws design inspiration from the golden age of Hollywood. The glamor of that era is captured throughout the space from the ornate chandelier to the 12-foot bar outfitted in antiqued mirrored panels, fluted brass, and natural green stone.