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The Essential Grey Flannel Suit

January 19th, 2021

5 ways to style the iconic grey flannel suit

What made people like Cary Grant, Fred Astaire, and Gregory Peck so stylish? Aside from talent, charm, wit, and dashing good looks, they dressed simply and timelessly. One of the staples in all of their wardrobes was a grey flannel suit. Here are five ways to style it.

1. The Classic

In the movie The Man in the Grey Flannel Suit, the suit itself is kind of a metaphor for conformity. A grey suit was a uniform for guys of the time. Self-expression wasn’t part of wearing a suit-it was just something you did. Today, it’s definitely more acceptable to add individual and even casual touches. I think a flannel suit, especially, is great for both. Here, I’m doing that with a turnback cuff on the shirt and knit tie with a squared-off blade for some effortless and low-key styling.

2. Seasonal Tie


If you like the idea of wearing a suit but don’t necessarily want the formality of a suit, flannel is a great vehicle for dressing up in a “dressed down” way. It feels and looks more relaxed and opens up more laid back styling options. The tie I’m wearing by Seaward and Stearn really “makes” this look, though. A great winter weight wool in a beautiful rust color. It’s got a bit of texture to it, which pairs well with the flannel. It’s a stand out piece, but doesn’t call too much attention to itself.

3. Funky Business


Showing the kind of casual dressed up styling for softness and playfulness that you can draw out of a grey flannel suit. The brushed cotton shirt from Luca Faloni is soft, unique, and really relaxes the overall vibe of the suited look. The tie is another standout–a kind of funky one from Drake’s. It’s a nice semi-thick but very supple wool with a brown and black houndstooth pattern. To keep that relaxed but dressy feel going, finish off with a pair of brown suede tassel loafers.

4. Jacket Separate


One of the best parts about a flannel suit is how easily it breaks down into separates. If you are a sport coat and jeans kind of guy, a flannel sport coat is one that you definitely want to have for the season. It’s one of the fabrics that pairs really well with the weight of denim. Underneath is simple layering with a white OCBD and light grey wool v-neck sweater. And anchored with a brown leather cap toe boot.

5. Pants Separate


Styling the pants as a separate here in a full-on winter mode with a brown herringbone double-breasted coat, Glenplaid sport coat underneath and then a winter white turtleneck. More casual here with a pair of tassel loafers.

Which look was your favorite? Chime in below.

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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Videography by Rob McIver

Video Editing by Ian Johnston


We received 100s of submissions for our call to be featured in the most recent video highlighting your best winter outfit ideas. To say it was difficult to pare it down to just 40 would be an understatement. It was even harder to choose 10 favorites from that list, but there were some gentlemen who really stood out to me and who I wanted to feature here.

You can't beat a good belted safari jacket. Especially one in a winter-weight with a subtle herringbone. An excellent combination of earth tones here and I'd like to particularly highlight the hunter green turtleneck.