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Article: The Gentleman’s Boots Handbook: From Chelsea to Chukka

2 Pairs of Chelsea Boots - Oswin Hyde

The Gentleman’s Boots Handbook: From Chelsea to Chukka

Boots are versatile pillars in any man’s wardrobe—transcending seasons and settings. Whether navigating city streets or weekend retreats, here’s how to choose and style the perfect pair.

1. Boot Styles Decoded

  • Chelsea boots for men: Sleek, elastic‑sided, slip‑on ease. Pair with slim denim or tailored trousers.

  • Chukka boots: Ankle‑height with open lacing—ideal for smart‑casual looks. Try our suede boots in earthy tones.

  • Dress boots: Lace‑up refinement in high‑shine leather—our men’s boots edit offers both derby‑style and cap‑toe designs.

2. Fit & Construction

  • Goodyear welted: Resoleable, water‑resistant, built to last.

  • Last shape: Rounded lasts suit casual builds; chiseled lasts deliver a dressier profile.

3. Colour & Material Choices

  • Classic black: Essential for formal and business attire—explore our men’s smart shoes and boots.

  • Rich browns & tans: Versatile for weekend wear—combines beautifully with navy and grey.

  • Suede finishes: Soft texture for spring and summer—browse our suede shoes for men.

4. Styling Tips

  • Cuff your trousers just above the boot to reveal the silhouette.

  • Layer socks: Wool or merino blends add comfort and climate control.

  • Contrast textures: Combine smooth leather boots with textured jackets or knitwear for visual interest.


Stride with Confidence
Discover boot styles that carry you through every season and setting.
🧑⚖️ Shop Chelsea boots
🍂 Explore suede & dress boots

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