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Derby Shoes – Five Plus One

Five Plus One is our weekly series of buyer’s guides. We pick a specific category and dig up five great options along with one that’s a little outside the norm.


Derby Shoes are one of the most classic styles of shoes. They feature open lacing, which inherently makes them a casual shoe, although they can certainly be dressed up to a business casual level with relative ease. Furthermore, their eyelets are attached to quarters that are the full height of the shoe (and wrap around the back); on the other hand, bluchers feature eyelets on small strips of leather that are sewn on opposing sides of the vamp. Whether you’re feeling pedantic or are just looking for a new piece of footwear, we hope you’re able to find what you want on this list.

1) Grant Stone: Country Derby

Derby-Shoes---Five-Plus-One 1) Grant Stone: Country Derby

If you’re looking for a single pair of derbies to wear into the ground, then Grant Stone’s Country Derby is the way to go. With their classic styling, Horween Chromexcel leather, Goodyear welt construction, and fantastic quality-to-price ratio, these are a no-brainer. The shoes are finished with antique brass eyelets and a studded rubber outsole, ensuring you’ll have adequate traction regardless of the weather.

Available for $298 from Heddels Shop.

2) Clarks Originals: Desert London

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Clarks Originals is most well known for the crepe soled desert boots, but their Desert London derbies are just as compelling of an option. While certainly a derby, these shoes feature a straight-cut on the bottom edge of the quarters which gives them a very unique aesthetic. They feature Clarks Originals’ stitchdown construction and crepe outsole, making these shoes incredibly comfortable. Best of all, these shoes come in a wide array of leather options allowing you to fill whatever gap exists in the your footwear rotation.

Available for $75+ from End Clothing.

3) Viberg: Shell Cordovan Derby Shoe

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If you’re simply looking for the best-of-the-best then you should certainly be considering Viberg’s Shell Cordovan Derby Shoe. Available in three shades of Horween’s famous shell cordovan, these derbies are made in Viberg’s low profile 2030 last with stitchdown construction and six hidden eyelets. It’s worth noting the uniqueness of Viberg’s pattern, as the quarters actually sit below the vamp rather than on top of it. These shoes are fully lined and are on a Dainite studded sole for maximum longevity.

Available for $1,070 from Viberg.

4) Oak Street Bootmakers: Plain Toe “Bluchers”

Derby-Shoes---Five-Plus-One-4)-Oak-Street-Bootmakers-Plain-Toe-Bluchers

While I may disagree every so slightly with the naming convention of Oak Street Bootmaker’s Plain Toe Bluchers, that doesn’t take away from one of the most attractive pair of derbies on the market. The simple design features minimal stitching lines, a 360° storm welt, and leather sole to make them both sleek and easy to dress up. That said, these shoes are equally easy to wear with a pair of jeans making them an ideal pair for just about any wardrobe.

Available for $256 from Oak Street Bootmakers.

5) Red Wing: Williston “Oxford” No. 9431

Derby-Shoes---Five-Plus-One-5)-Red-Wing-Williston-Oxford-No.-9431

Red Wing’s Williston Oxfords might not technically be oxford, but hey a derby by any other name, right? These shoes are a great example of the fantastic new styles that Red Wing has been developing. With their low profile toe, monochrome black palette, hidden eyelets, and cord half-sole, these shoes are just such an easy pair to grab in the morning and wear as your daily drivers.

Available for $400 from Grown and Sewn.

Plus One – Grenson: Curt Triple Welt

Derby-Shoes---Five-Plus-One-Plus-One---Grenson-Curt-Triple-Welt

Grenson’s Curt Triple Welts are some of the most unique derbies on the market. As their name implies, these shoes feature three welts, which are stacked and feature pinking for unrivaled gaudiness. However, the rest of the shoe is so understated that it somehow doesn’t look out of place after staring long enough. The width of three welts do result in an abnormally large footprint, but honestly that’s part of these shoe’s charm. You’ve just got to embrace it.

Available for $645 from Grenson.