He Spoke Style

Gray Prince of Wales Flannel Sport Coat

$1,800

or 4 interest-free payments of $450.00 with Affirm.

This is a custom made-to-measure product.

The Prince of Wales check, also known as Glen Plaid, is one of the most enduring patterns in menswear. Interpreted in flannel, it becomes a foundational piece for fall and winter—classic, refined, and endlessly wearable.

Cut from premium cloth by Loro Piana, the fabric sets the standard for quality, offering an exceptionally soft hand-feel and a natural, elegant drape that elevates the entire garment.

Key Features:

Classic gray Prince of Wales (Glen Plaid) pattern
Luxurious flannel from Loro Piana, prized for softness and drape
Ideal weight for fall and winter wear
Designed to pair effortlessly with tailored trousers, knits, and denim

Timeless Winter Tailoring:

The pattern provides depth and visual interest without overwhelming the look, striking the perfect balance between tradition and modern relevance. Flannel enhances its warmth and texture, making it especially suited to cooler months.

Versatile by Design:

Wear it with matching flannel trousers for a coordinated look or style it on its own with solids and textured layers. Equally appropriate in professional settings and more relaxed environments, it anchors a well-considered wardrobe.

Why I Love It

I have always believed in maximizing every garment you own, and this jacket is the perfect example of that philosophy. The rich Loro Piana flannel texture allows it to break away from the full suit effortlessly, serving as an ideal anchor for a classic business casual look.

My Try-On Size

We will use the information below to provide a suggested try-on size based on extensive data and experience.

Regrettably, we do not have a try-on garment in your size.

Height	Height (Feet) Height (Inches)
Weight	Weight (Pounds)

My Try-on Size

Based on your height and weight, we recommend sending you the following size try-on garment(s) to check your sizing. You can select a different size if you are confident the suggested size is not your preferred fit.

We recommend that you stay within 1–2 sizes of the recommended try-ons, which are based on extensive data and experience. If the fit is significantly off, you may request one additional size. Try-ons must be returned within two weeks for a refund; after three weeks, they’re considered misappropriated and the order will be canceled with payment applied to replacements.

Jacket Try-On	Jacket Try-On (Available) (Currently Unavailable) View Size Chart

Try-on garment Measurement guide

Now that you've received your try-on garment, it's time to assess the fit and make any necessary corrections -- this is the first step to achieving your personalized custom fit. I'm about to personally walk you through the entire assessment process, but first let's make sure that you have been sent the correct try-on garments for you. Watch this introductory video before beginning your fit assessment.

Customize

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Additions

Sartorial Upgrade $150

Made To Measure

How Our Process Works

Browse and select your garments

Each piece is highly considered and personally curated by HSS founder Brian Sacawa based on his own wardrobe. While shown in Brian’s suggested styling, each garment can be customized to meet your personal tastes.

Receive your try-on garment

Typically in less than two weeks you’ll receive your try-on garment and that will serve as a test where you will be able to review the fit to make any necessary adjustments.

Make Adjustments To Your Size

Once you receive your try-on garment, we will walk you through the process of how to assess the fit of your garment and make any necessary adjustments to achieve your personalized custom fit.

Receive your made-to-measure suit

In about four weeks after your test fitting, you will receive your final garment(s). Try not to gloat too much as your friends envy your new clothes.

To learn more, please read our FAQ.

Gray Prince of Wales Flannel Sport Coat

$1,800

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