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Harry Styles Makes a Case for the Winchester Shirt

22 May, 2026 | Josh Newham

Harry Styles wears Savile Row Company? Not quite, but he was wearing one of our best-selling styles: the Winchester shirt.

Performing at the Johan Cruijff Arena in Amsterdam during his Together, Together tour, the singer stepped onto stage in a blue and white Winchester shirt paired with a floral tie — a reminder that the contrast collar shirt remains one of menswear’s sharpest details.

What Is a Winchester Shirt?

Men's pin collar Winchester shirt

The Winchester shirt — also known as a contrast collar shirt — is a classic men's formal shirt defined by its crisp white collar and cuffs set against a coloured or patterned body.

A long-standing feature of British tailoring, it became synonymous with 1980s power dressing and has appeared everywhere from Wall Street to James Bond films. Smart, structured and understated, it remains one of the easiest ways to elevate formalwear.

Harry Styles and the Return of the Contrast Collar


Harry Styles has built a reputation for mixing classic tailoring with expressive detail, and his Amsterdam look struck exactly that balance. The floral tie softened the structure of the Winchester shirt, giving the traditional silhouette a more relaxed, contemporary feel.

It also proves the versatility of the men's Winchester shirt: equally at home with sharp suiting, patterned ties or more modern styling.

How to Wear a Winchester Shirt

The Winchester shirt works best when kept simple:

  • Navy tailoring and a silk tie for classic formalwear
  • Patterned or floral ties for a softer, more expressive look
  • Open collar styling under a blazer for a more relaxed approach

If you’re looking to recreate the Harry Styles look, pair a contrast collar shirt with one of our patterned silk ties. Floral designs offer a more contemporary feel, while classic tonal styles keep things firmly in traditional territory.

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