What to Wear with Sperry Top-siders: 5 Outfit Ideas

This original brand of boat shoes owes its worldwide popularity to the fact that it connected comfort and style. These shoes were designed by an avid boater Paul Sperry in 1935 with specially designed soles that were supposed to make it easier for boaters and sailors to maintain traction on slippery surfaces.

Nowadays, Sperry Top-siders are definitely one of those shoes that every girl should have, and if you are considering buying a pair, or you already own one, here are some ideas on what to wear with them:

1. All-Denim

We do not normally recommend outfits completely made of denim but Sperry Top-siders will allow us to make an exception to this rule. This is probably the only shoe that goes extremely well with all-denim outfits. You can combine your denim shorts, and a jean shirt, with light brown or beige Sperrys, and with some accessories you will look, and feel, very fashion.

All Denim Outfit Combination with Sperry Topsiders Shoes

  • Shoes: Sperry Top-sider Boat Shoes
  • Top: G-STAR Nikki Sleeveless Chambray Shirt
  • Shorts: Paige Premium Denim Jimmy Jimmy denim shorts
  • Bag: Gucci Vintage Backpack
  • Accessories: BINDYA Ombre Modal Scarf

2. Let’s Go Sailing

Since Sperrys were initially invented for professional, or amateur, boaters it is only natural that they go well with sailor outfits. It’s hard to picture a sailor look without Sperrys.

Sailing Outfit Combination with Sperry Topsiders Shoes

  • Shoes: Sperry Top-Sider Authentic Original 2 Eye
  • Shorts: Oasis Lace Denim Shorts
  • Top: Karin Tee
  • Bag: MAR Y SOL Aix Straw Beach Tote

3. Now, Let’s Take It up a Notch: the Yachting / Polo Look

The sailor look re-adapted to meet high-end society needs, when it comes to spending time offshore, can be easily turned into a daily outfit for active and athletic girls. Choose some dark denim jeans, a polo t-shirt and some white Sperrys and, who knows, maybe somebody will take you yachting. Or maybe to a polo match.

Polo Outfit Combination with Sperry Topsiders Shoes

  • Shoes: White Sperry Top-siders
  • Jeans: Citizens of Humanity Dani – Scorpio
  • Top: Ralph Lauren Polo T-Shirt
  • Watch: Michael Kors Brown Leather Strap Chronograph Watch

4. The City Look

Sperrys can be combined with various urban outfits for a perfect city look. They go well with denim Bermuda shorts, pleated skirts, ankle pants or Capri pants. You can even wear them with casual dresses. Combine your big city girl outfits with your Sperrys and rock the town.

Casual Outfit Combination with Sperry Topsiders Shoes

  • Shoes: Sperry Top-Sider
  • Pants: Bardot Tische Trouser
  • Top: London skyline burnout tee
  • Outwear: MOTO Sparkle Yoke Crop Jacket
  • Accessories: Ted Baker COOPER – Aviator sunglasses

5. The Safari Look

Boat shoes and earth colors make a perfect Safari outfit. Even though the herringbone groove pattern on the soles is made for balancing on the slippery boat decks, these shoes will do well on any surface.

Safari Outfit Combination with Sperry Topsiders Shoes

  • Shoes: Sperry Top-Sider Authentic Original 2-eye boat shoes in twill
  • Shorts: Organic by John Patrick Hip Short
  • Top: Boyfriend Loose Blouse
  • Bag: PROENZA SCHOULER Small leather bag
  • Accessories: Leva Round Wood Earrings with Marquis

Cover photo: www.etsy.com

About the author


Lisa is a young lawyer with various interests and hobbies to keep her mind off her work at times. She is a true fan of contemporary American literature, European movies, Asian food, African Wildlife and all those little things in life that make us genuinely happy.


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