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Wedge Soled Boots – 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.


If you are looking for a pair of casual boots to be you daily drivers there is no better choice than a pair featuring a wedge sole. While this style of boot is purely for casual wear, the overall comfort and glide of the wedge sole can really make it worth the tradeoff.

1) Tricker’s: Churchill Boot

Wedge-Soled-Boots---Five-Plus-One-1)-Tricker's-Churchvill-Boot

If you are at all familiar with quality British footwear then you likely know and love Tricker’s. With their classic styles and quality construction, it’s hard but to consider them every time you’re looking for a new pair of boots. Their Churchill Boot features a derby style upper with a brown, Vibram 2060 sole that matches the chocolatey colored leather perfectly. This pair is finished with brass eyelets and a 360º storm welt making this one compelling pair for the coming rainy season.

Available for $545 from Division Road.

2) Red Wing: 8818 Moc Toe

Wedge-Soled-Boots---Five-Plus-One 2) Red Wing: 8818 Moc Toe

Red Wing is well known for their classic moc toe styled boots, and their 8818 suede/smooth combo color way is a great new addition. While the dual-leather style might not appeal to everyone, it’s great to see Red Wing doing something a bit out of their comfort zone and the duo of leathers pairs beautifully with the nickel eyelets and white stitching. This boot is finished with tan traction tread sole, which gives this boot a bit more contrast.

Available for $315 from End Clothing.

3) Viberg: Scout Boot in Natural Chromexcel Roughout

Wedge-Soled-Boots---Five-Plus-One-3)-Viberg-Scout-Boot-in-Natural-Chromexcel-Roughou

While Viberg is most well known for their stitchdown Service Boots, that doesn’t mean their Goodyear welted Scout Boot is any less compelling of an option. Made with natural Chromexcel rough out leather and a Vibram Morflex wedge sole, this boot is going to be one of the most comfortable you own (once it’s broken in, of course). It’s worth noting that Vibram’s Morflex outsole is a bit foamier and lighter than their regular Christy outsole.

Available for $670 from Viberg.

4) Yuketen: Maine Guide DB

Wedge-Soled-Boots---Five-Plus-One-4)-Yuketen-Maine-Guide-DB

True-moc constructed shoes and boots are known for being incredibly comfortable, and Yuketen’s inclusion of a Vibram Christy sole on their Maine Guide DB is sure to make it every more comfy. While the multi-color colorway of these boots can be polarizing, it’s just one of the many styles they offer. Completed with four eyelets and three speedhooks, these boots are as easy to put on as they are comfortable to wear.

Available for $627 from Yuketen.

5) 1892 by Thorogood: Chukka Boot

Wedge-Soled-Boots---Five-Plus-One-5)-1892-by-Thorogood-Chukka-Boot

1892 by Thorogood’s Chukka Boot is a great option for those of you who want a pair of wedge soled boots but prefer the look of chukkas. Made with their highly textured caliber wedge outsole, these boots feature a heavily oiled predator leather that accentuates all the natural irregularities in the hide in the best way possible. With their low price and made in Wisconsin quality, you’ll be happy to have these boots on your feet for years to come.

Available for $180 from Context Clothing.

Plus One – Visvim: Virgil

Wedge-Soled-Boots---Five-Plus-One-Plus-One---Visvim-Virgil

Visvim has always been a brand that is either loved or hated, and their Virgil boot is one of their most iconic pieces. Easily identifiable by its TPU heel stabilizer, this iteration of the Virgil features a custom Vibram outsole that is one of the most interesting wedges on the market. These boots are finished with cotton laces, a deerskin tongue tab, hand-dyed vegetable tanned leather, and a cork footbed to ensure they grow to the shape of your foot.

Available for $1075 from Blue Owl.