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Fashion glossary

Topsiders: What They Are, What They Are, and What to Wear Them With

Olena Kovalenko 2 min read

What are topsiders?

Topsiders (from the English topside - upper deck) - these are classic low shoes with a flat grooved sole, originally developed as specialized footwear for yachting.

Read also our full guide: Types of Women's Shoes: Why the Old Rules Don't Work
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Classic leather topsiders with a white sole and a distinctive seam on the toe

When discussing topsiders, it's important to note their functional origins: the shoes were created in 1935 by yachtsman Paul Sperry for safe navigation on wet and slippery decks. The design was intended to securely hold the foot and avoid leaving dark marks on the yacht's light-colored surfaces.

Distinctive features

The design of topsiders includes several mandatory functional elements.

  • Sole: Traditionally made from white rubber with a special wave tread that provides maximum grip on wet surfaces.
  • Lacing: A leather lace passes through metal eyelets around the entire perimeter of the heel and is tied at the front (usually 2-3 holes), which allows the shoe to be securely fastened to the foot.
  • Material: Classic models are made from soft leather or suede, often treated with a water-repellent finish.
  • Toe: It is decorated with a characteristic semicircular outer seam, visually reminiscent of the design of moccasins.
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A smart casual look for women with brown leather topsiders, cropped chinos and a Breton top
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Pastel blue suede topsiders with contrasting white laces

What to combine with

The main rule for wearing topsiders is that they should be worn barefoot only. For hygiene reasons, invisible footmuffs, which are completely hidden under the shoe, are allowed.

Topsiders are a basic element of the preppy style and fit harmoniously into smart-casual summer looks.

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An example of a summer capsule: blue topsiders, white denim shorts and a light blue linen shirt

In a women's wardrobe, successful combinations include cropped chinos, Bermuda shorts, straight-leg jeans with cuffs, as well as lightweight linen shirtdresses and A-line skirts. Tops can include Breton tops, polo shirts, and basic T-shirts, accessorized with a lightweight blazer or a cotton jumper draped over the shoulders.

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About the author

O
Olena Kovalenko

Stylist with 14 years of experience. Specializes in capsule wardrobes and seasonal style transitions. Has helped over 500 women find their personal style and dress with confidence every day.

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