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Chukka 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.


For those who want footwear a bit more substantial than shoes without going for full-on boots, chukkas are the obvious answer. And to make things even better, chukkas come in a wide range of formality levels; for many of us, they’re the perfect style of boot if you will need to dress one pair both up and down. We’ll cover a wide range of boots in this post, so take a look around and find a pair that you like.

1) Meermin: Chukka in Black Calf

Chukka-Boots---Five-Plus-One 1) Meermin: Chukka in Black Calf

1) Meermin: Chukka in Black Calf

First up is Meermin, known for their high-quality and reasonably-priced footwear. Their Chukka in Black Calf is a great choice, especially if you’ll need to wear them in both formal and casual situations. They’re made with three eyelets, which allows for tighter lacing than on the common two-eyelet style. This pair features a studded rubber sole, which is great for keeping a low profile without the slipperiness of leather outsoles.

Available for $210 from Meermin.

2) Löf & Tung: Cole Chukka in Tobacco Suede

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It doesn’t get much better than a beautiful suede boot, and the metallic undertones of Löf & Tung’s Cole Chukka in Tobacco Suede certainly make it one of the more eye-catching models on the market. These boots feature a classic, almond-toe shaped last with two eyelets, a studded Dainite outsole, and a 360° welt. While the style and leather choice of these shoes make them a bit more casual than some, they could certainly be used for a business casual outfit on occasion.

Available for $345 from Skoaktiebolaget.

3) Red Wing: 3322 Weekender Chukka in Copper Rough & Tough

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Red Wing Heritage is one of the most suggested brands for quality, casual boots, but there has always been one complaint for me: their bulbous lasts. That said, their new Weekender Collection has changed all that. The 3322 Chukka in Copper Rough & Tough features a lower profile toe, stitchdown construction (rather than Red Wing’s usual Goodyear welt construction), and their famous Rough & Tough leather that ages beautifully. While this boot exists firmly in the casual category, it’s a hard option to get past.

Available for $275 from END.

4) Alden: Chukka in Color #8 Shell Cordovan

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Alden is well-known for both their chukkas and their in-house-overdyed color #8 shell cordovan, and their Chukka in Color #8 offers both. This simple boot is made on double leather sole with Alden’s 360° split reverse welt, making for one of the most classic and clean boots on this list. While some may argue that shell cordovan began as a workwear leather and is thereby unsuitable for formal situations, most would say this boot is fully capable of being dressed up or down.

Available for $774 from Leffot.

5) Heschung: Genet Chukka in Cafe Brown

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Heschung’s designs are always a bit more unique than many others on the market, and their Genet Chukka in Cafe Brown follows suit quite well. It may not stand out, but it certainly features some great, subtle detailing such as the mild curve where the quarter meets the vamp, the curves where the quarters meet to be laced, and the Norvegese welt. These boots are made in France with a latex outsole and a calf suede that is both beautiful and durable.

Available for $330 from No Man Walks Alone.

Plus One – Dunhill: Chukka in Grey Suede

Chukka-Boots---Five-Plus-One-Plus-One---Dunhill-Chukka-in-Grey-Suede

There are a lot of great chukkas on the market, but Dunhill’s Chukka in Grey Suede is certainly one of the most memorable pairs. The stitchdown construction, crepe outsole, wholecut pattern, and French binding make this pair really stand out from the rest, and will make them the centerpiece of any outfit. While they’re available in several colors, the grey suede just feels at home with the rest of the boot.

Available for $725 from Mr. Porter.