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Jack Erwin Review: Investment Chelsea Boots at Everyday Prices

Jack Erwin is a men’s shoe company based in New York City and founded in 2013. Creating truly timeless men’s shoes, Jack Erwin has partnered with the finest factories and artisans in France, Italy and Spain, designing custom styles available only on their website and its Tribeca Fitting Room. Eliminating costly markups and middlemen that drive up the costs, their quality dress shoes come at a fraction of the price.

Everything begins with the last. Before considering materials, colors, patterns, and outsoles, the last is designed. A last is the form from which a shoe is built. It dictates the shoe’s fit, feel and silhouette. But they do even more than that; they are the ethos of each Jack Erwin Collection.


Jack Erwin shoes are a result of an uncompromising commitment to turning their vision into reality. They meticulously design each shoe to be confident yet reserved; to stand on its own yet complement others within its respective collection.


They brainstorm about every single detail and test creams, polishes, and finishes to create the perfect final product.


The result are timeless pieces of footwear no true gentleman would ever resist. Some of the iconic styles, such as Penny loafers, Wingtip Oxfords and Chelsea boots are a truly great investment at Jack Erwin.


The Sullivan Collection features a rounded silhouette and pronounced toe box that perfectly pairs with our substantial Goodyear-welted outsole. In this collection you’ll find all your classics, perfect for your busy week schedule.

Jack Erwin Review


I’ve been wearing around town a pair of Ellis, the Chelsea Boot, and absolutely love them.

The suede is polished, pliable, and soft. My biggest complaint about chelsea boots is it being tough to slip them on. This is not the case with Jack Erwin, the foot cup easily allows my feet to slip into the shoes, making them candidates for air travel where I may need to remove my shoes in a rush at the airport.


Commons Projects and Jack Erwin: Switched at birth?

When I put on the shoes and started looking at them, the closest comparison I found was to my pair of Common Projects Chelsea boots. The CPs have a gummy sole, which makes them more casual, whereas the Jack Erwin’s have a leather sole, making them a bit more dressy and capable to do duty with your daily suit.

The quality and finish is there, and the Jack Erwins are about 60% less, which means you could buy a pair of Jack Erwins in all three colors for the price of one CP.

Jack Erwin Lines

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Each shoe within the Foster Collection shares a last characterized by a tapered and defined toe box that is perfectly paired with our low-profile Blake-stitched sole. Just what you need for your next dress up occasion.

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The Wright Collection is featuring a range of loafers well-suited for your off-duty days, each shoe is designed using one of two lasts for an easy, effortless wear.

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Shop handcrafted footwear at Jack Erwin.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities. Lifetailored has partnered with Creditcards.com for our coverage of credit card products. Lifetailored and Creditcards.com may receive a commission from card issuers Additional Disclosure: This site has affiliate links. We may be compensated when users make a purchase or register to a third party website. For more details read our privacy policy.

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