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wearing a gray chalkstripe flannel suit for a formal occasion
wearing a gray chalkstripe flannel suit for a formal occasion

Unlock the Timeless Elegance of a Gray Chalkstripe Flannel Suit

March 8th, 2023

An Essential & Elegant Winter Workhorse

There are a handful of things I truly look forward to when summer finally ends and we get into the fall and winter months. Stacking my just-delivered cord of wood in anticipation of our first indoor fire of the season. The prospect of snow blanketing the beautiful landscape. (I’m from Upstate New York and I actually like the snow!) Pulling out my heavy wool coats. And, you guessed it, swapping out my cotton and linen suits for perhaps my favorite suit style of all time—the chalkstripe flannel suit.

It’s hard to describe, but there is just something about the look and feel of a chalkstripe flannel suit. Of course, there’s a level of formality—it is a suit, after all. But mixed with that formalness is a feeling of effortless and casual sophistication.

brian sacawa at pitti uomo 103 wearing a charcoal greatcoat near the ponte vecchio

I realize that “formal” and “casual sophistication” may seem incompatible. How can something be both of those at the same time? But in the case of the chalkstripe flannel suit, I really believe they’re two sides of the same coin. I said it was hard to describe.

So for those looking for a fall/winter suit that can do formal and not necessarily feel so formal, look no further than a gray chalkstripe flannel suit.

What is a Chalkstripe Suit?

detail of a double-breasted gray chalkstripe flannel suit styled with a white shirt and black tie

The chalkstripe is a popular style for menswear connoisseurs and is named after the line made by a tailor’s chalk. This particular stripe style is typically long, vertical, and continuous, with the stripes consisting of two to five threads woven directly into the suit material. While not as pronounced as pinstripes, chalk stripes add an elegant touch to any suit.

The spacing between the stripes can vary, and typically the narrower the spacing, the more formal the attire appears. Additionally, the spacing between stripes can affect the overall appearance of the suit, with wider stripes giving a more bold and daring look, and narrower stripes giving a more subtle and sophisticated look.

Overall, the chalkstripe flannel suit is a versatile option for those looking to add some variety to their suit wardrobe and take their menswear game to the next level.

Further Reading: Chalkstripe vs. Pinstripe: What’s the Difference?

How to Dress It Up Formally: My Formula

brian sacawa sitting in an ornate chair wearing a db gray chalkstripe flannel suit

The photos in this post were taken during my recent trip to Florence to attend Pitti Uomo for the very first time. In addition to checking out the fair at the Fortezza during the day, there were evening events to attend, spanning the spectrum from black tie soirées to casual dinners. On this particular evening, I was attending a gathering hosted by the fine folks at Plaza Uomo.

Anyone who’s gone to Pitti before knows that you can pretty much wear anything to anywhere and nobody will bat an eye or pass judgement. Tuxedo for lunch at Sostanza? Why the hell not?

And while there were certainly dudes all kitted up in black tie at the Plaza party, I was feeling formal, but just shy of black tie. So I ended up taking my own advice and going with our double-breasted gray chalkstripe flannel suit.

brian sacawa attending pitti uomo wearing a gray chalkstripe flannel db suit

When I’m styling this particular suit for a formal occasion, I always stick to the same basic formula: white poplin shirt, black cap toe oxfords, and a black grenadine tie. The extreme high contrast of these items paired with the mid-tone gray of the suit creates a very harmonious (and formal) appearance.

You may be inclined to ask why I chose a grenadine tie, which is generally a notch down on the formality scale for neckwear. Wouldn’t a nice 50oz silk number have been better?

And, to that, I would say “better” is subjective.

I chose grenadine for two reasons. First, I love the texture of a grenadine tie. And second, I think it’s a great complement to flannel. (Okay, and third . . . it’s just so much fun to tie—perfect every time.)

wearing a charcoal wool and cashmere belted greatcoat

With a chill in the air that evening, I also chose to don our new wool/cashmere blend charcoal gray greatcoat. Super timeless and elegant, not to mention quite warm thanks equally to its quilted lining and classic length.

The Takeaway

When styling a double-breasted gray chalkstripe flannel suit for a formal occasion, it’s best to keep things simple and high-contrast. White shirt. Black tie. Black Oxfords. And throw on a charcoal overcoat for warmth.

Of course, there are many variations here. Take my formula and riff on it. For example, if you’re going for a bit more relaxed sophistication, try a black merino wool turtleneck.

As always, start with something tried and true and adapt to your taste.

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

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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