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Style October 12th, 2023

1 Piece, 5 Ways: Brown Glen Plaid Flannel Sport Coat

Style October 12th, 2023

What To Wear With A Glen Plaid Sport Coat

As much as I love wearing a suit, I have to admit that it often feels a bit too formal. For example, last week for my birthday we had a dinner reservation at one of my favorite restaurants. Since it was an “occasion,” I thought a suit would certainly be apropos and I was looking forward to wearing one. But when I actually suited up it felt like a bit much and something just wasn’t working.

Could it have been that it was the middle of the week? Was it that it was still light outside? I honestly don’t know. But what I did know was that my navy blue flannel suit outfit wasn’t working for me that night. And I also knew that if I needed to figure out a Plan B pretty quickly.

Now don’t get me wrong, I am an extremely strong advocate for making any occasion the occasion you want it to be in terms of what you choose to wear. We always dress in formalwear for our annual New Year’s Eve dinner reservation while the rest of the crowd typically sports a button-down shirt, trousers, loafers, and layered burgundy v-neck sweater. We never think twice about it and never feel out of place.


Recently, however, when getting “dressed up” I find myself gravitating to a casually tailored approach with a sport coat and trousers. It’s relaxed and comfortable while still looking incredibly sharp and smart. And the sport coat that I find myself reaching for quite a bit this fall is my classic and versatile brown Glen plaid flannel sport coat.

Here are five ways I’ve been wearing it.

1. Getting Tonal

If you’ve been following HSS for any length of time, you probably know at least two things about me. One, I love a good tonal/monochromatic outfit. And two, brown is one of my go-to colors. To the second point, a commenter on my YouTube channel once sarcastically remarked that I should seriously consider changing our name from He Spoke Style to He Spoke Brown. Duly noted! So, yes, I do love brown (for any season, in fact), but there is perhaps no better season for brown than fall.

When putting together a tonal look like this, there are three keys to pulling it off convincingly. First, choose different shades of whatever color you’re working with. This will ensure that there is some contrast and definition between each garment, helping to create a more harmonious appearance.

Second, choose fabrics that pair well together. Since the focal point of this outfit is the brown Glen plaid flannel sport coat, you could certainly make things easy on yourself for trousers by choosing a pair in a matching fabric. I haven’t done that, instead opting for our not-shiny-at-all chocolate brown sharkskin trousers; which I paired with a pique knit dress shirt for even more contrast.

And third, add a pattern to break up the one-color monotony and keep things visually interesting. That’s where a brown Glen plaid sport coat really shines. I love how it adds a classic touch to the more modern monochromatic styling.

2. Layered Sweater


If you’ve been reading the blog faithfully since we relaunched the site, you’ve seen a lot of flannel—it is fall, after all—and you’ve heard me talk (almost) ad nauseam about its incredible versatility. Perhaps no other sport coat is more versatile than a flannel sport coat—tweed is a close second—because of the ease with which you can pair it with denim. And if you’re a jeans and sport coat kind of guy, this outfit is for you.

This is the ultimate fall classic. Slim dark denim. Classic white dress shirt. Burgundy cashmere crew neck sweater. Dark brown wingtip brogues. And the brown Glen plaid flannel sport coat to finish the look off, break the solid colors up, and draw your eye upward towards my face.

One note on styling a sport coat with a layered sweater. Whenever I put together a look like this, I never button the sport coat. This is all about balance and this outfit is a very nice illustration of that concept.

3. Casually Tailored

The idea of dressing casually tailored has been seeping into the menswear lexicon over the past couple of years to the point where I might even call it a trend. And while I don’t normally get behind “trends” per se, I have to say that the casually tailored trend is one that I wholeheartedly endorse.

I really like the idea of casual tailoring because it goes pretty far towards breaking down the boundaries of what it means to dress well and dress up. For quite some time now, guys have been conditioned to think that dressing up meant having to wear a suit. But there is an entire realm of “dressing up” to explore that has nothing to do with wearing a suit and that’s where casually tailored comes in.

It’s all about utilizing classic menswear basics in a natural, casual, and almost nonchalant way. Think about it as the more advanced sartorial equivalent of jeans and a t-shirt. A pair of charcoal gray flannel trousers may seem like a pair of pants that were made to be “dressed up” but pair them with a denim shirt, brown Glen plaid flannel sport coat, and cordovan penny loafers, and well, you’ve just changed the game.


4. Low Key Luxe

Here, we’ve got another brown tonal outfit built upon the same principles as the first look in this post—different shades of the same color, complementary fabrics, and a pattern to break things up. Same idea, completely different vibe, and a great illustration of how a couple of small tweaks can transform a look from sharp to sophisticated.

First, instead of darker colors, here, we’re dealing with lighter shades of brown for the outfit’s foundation. There’s something very chic and “quiet luxury” about that particular color palette. I’ve often wondered exactly why and the best I can come up with is that it’s familiar but also quite distinct and unexpected at the same time. In other words, simple and subtle yet uncommon enough to turn heads without much fanfare at all.

The second small tweak has to do with fabrics and here I’m specifically talking about the cashmere turtleneck. Again, it’s very subtle and mostly imperceptible to the casual observer but there is something almost intangibly elegant about cashmere in this situation even paired with cotton pants.

This particular outfit really shows off the versatility of a brown Glen plaid flannel sport coat and how a classic pattern can be equally at home in a variety of styling situations.

5. Simple Statement

In all my talk about how classic and versatile a brown Glen plaid sport coat is, I suppose the one thing I’ve failed to mention is that it is something of a statement piece. Now, obviously we’re talking a much different level of statement compared to something from the defunct Thom Browne x Brooks Brothers Black Fleece line but if I’m being honest, no matter how classic a Glen plaid pattern is, it does stand out.

And, as always, the best way to style a stand out statement piece is to keep the rest of the outfit as simple as possible. Doing so allows the “statement” garment to be the focal point of the outfit. Here, that’s accomplished with a simple white poplin dress shirt, classic mid-gray flannel trousers, and medium brown split toe derbies. Doesn’t get much simpler than that. No pocket square necessary.

The Bottom Line

A brown Glen plaid flannel sport coat is an absolute must-have for your fall and winter wardrobe. It’s incredibly versatile, can easily be paired with jeans, and its classic pattern can be styled classically or in more contemporary scenarios. Let me know which look was your favorite and how you would style this piece down below in the comments.

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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