Harry’s Guide to: Heritage Patterns

Named after its resemblance to herring fish scales, herringbone is essentially a twill with an alternating pattern, also known as "broken twill." Its origins date back to Roman times when it was used in their road construction.

The Romans used herringbone interlocking stone to create durable roadways, reflecting the gravity of their empire's infrastructure needs. In the 1800s, the pattern found its way into Irish tweed, bridging historic urban planning with modern fashion.

Today, herringbone is crafted from heavy wool, lightweight cotton, and even linen, making its way into suits, overcoats, and shirts. A full herringbone suit is a favorite of James Bond, from Connery to Craig. To channel that 007 look, opt for jackets in grey, navy, or brown, paired with a shirt and tie for a super spy meets business formal style. For a more relaxed approach, a herringbone sport jacket with denim or an Oxford shirt will carry you through with sophistication.

If houndstooth appears dizzying at first glance, it’s doing its job. Houndstooth, designed for camouflage, originated in the Scottish Lowlands, where shepherds used white and black sheep's wool in a jagged pattern to create the illusion of distance from onlookers. While it dates back to 360-100 AD, houndstooth gained popularity in the 20th century when aristocrats embraced it for a countryside look. Edward VIII and Cary Grant famously sported houndstooth.

When wearing houndstooth, consider scale: larger patterns are less formal. Opt for medium-to-large houndstooth in brown or burgundy for outerwear. Smaller "puppytooth" patterns are versatile and work for suits, shirts, ties, or pocket squares.

Glen check, often misused, combines small and large broken checks, including houndstooth, typically in muted colors like black, grey, and white. Glenurquhart checks resemble glen checks but have a different colored overcheck. The Prince of Wales check, worn by Edward VII and popularized by Edward VIII, is similar to the glenurquhart but larger in scale. You can interchange glenurquhart and Prince of Wales as both fall under irregular checks.

In styling, coordination and accessorizing matter. A grey glen check suit offers versatility with various shirt and tie combinations. With glenurquhart and Prince of Wales, you introduce a third color, allowing you to play with the color wheel without being too matchy-matchy.

Remember, when President Reagan wore a Prince of Wales suit in Europe in 1982, it turned heads. Embrace the confidence of this menswear classic and don't be afraid to make a statement.

Checkerboard weaves, including the windowpane check, have a long history dating back to around 10,000 BC. However, the windowpane check as we know it gained popularity in the 1920s as a rival to pinstripes.

The windowpane check stands out due to its larger checks, resembling divided windowpanes. Whether worn on a suit or an overcoat, this pattern is visually striking from a distance and up close, offering a strong and consistent look.

When styling windowpane checks, similar rules to stripes apply—keep the rest of your outfit understated to let the pattern shine. You can choose between solid or chalk lines for your windowpane checks, as seen on Jamie Foxx in a fleck suit while portraying Ray Charles.

The origins of pin- and chalk striping in menswear are debated, with some linking it to banking rank displays and others to sporty boating uniforms. Nevertheless, these sartorial patterns originated in England between the late 18th and early 19th centuries.

In the Victorian era, stripes first appeared on pants, helping identify bankers and their institutions by stripe thickness and spacing. Over time, stripes made their way onto full suits and gained popularity in the United States, embraced by various figures, including jazz musicians and gangsters like Al Capone, along with style icons like David Bowie.

Pinstripes consist of fine lines, as narrow as 1/30 inches, woven separately into the fabric, creating a distinctive, defined look. In contrast, chalk striping is thicker and blends into the fabric background, resembling the chalk a tailor uses when designing a bespoke suit.

When choosing stripes, remember that finer stripes are more formal. Consider the fabric: smooth worsted fabrics pair well with sleek pinstripes, while the fuzzy, loose nature of flannel complements chalk striping. A plain, crisp white shirt complements a navy, grey, or black pinstripe suit, but you can also mix it up with a different button-up—just ensure the shirt's stripes differ in scale from those on your jacket.