Review: Carter Wingtip Boots by Jack Erwin

I got these Carter wingtip combat boots from Jack Erwin a while ago and gave them a good test run. I wear them to work or school when I have to ride the motorcycle.

UPDATE: Added a new video review below!

First the (sort of) bad: these things cost $220! While high-quality shoes can easily cost much more than that, it is still on the expensive side compared to other online start-ups like Beckett Simonon or even more established retailers Charles Tyrwhitt, if you use promo codes (which are abundant).

Speaking of which, according to their website, Jack Erwin never offers promo codes or discounts. You’ll have to pay full price, but at least you won’t have to wait for an arbitrary sale to come around.

Presentation: Shipping is free. Everything comes in a sturdy, oversized shoebox. Customers ares greeted with a thank you card and a large felt dust bag. Very nice. Also included are an optional set of sole inserts, which for some reason are made in Portugal (the shoes themselves are made in Spain).


Fit: These size noticeably smaller than the other shoes I’ve tried lately (even though on the outside they look huge). I’m usually 10 to 10.5 in sneakers, and I often have to size one full size down for dress shoes. I ordered these in 9 and they were still too big. Too much room in the heel. I had to exchange them for 8.5.

EDIT (08/10/15): Just received an email from Jack Erwin stating that sizing will follow US standards, meaning if you are a normally size 9, you should buy a size 9.

Customer service: Thankfully, return shipping was free. The representative I corresponded with was helpful and attentive; perhaps not as attentive as Beckett Simonon (who sent me two sizes simultaneously so I could pick the best fit and return the other) or Charles Tyrwhitt (probably the gold standard in customer service).

Oddly, the replacement pair did not come with the extra inserts. I contacted customer service again and they shipped me a pair without any fuss.

Construction: Jack Erwin shoes are made from full-grain leather and are goodyear welted for durability and resoleability. This is important. However, the leather on these boots is thicker I’ve seen on other shoes. As a result, they are quite stiff and heavy – definitely not the most comfortable shoes, at least not out of the box. When I first started wearing them, they cut into my ankles. But they broke in considerably after a few weeks, and while they’re still kind of stiff compared to my other shoes, they aren’t uncomfortable.

Appearance: You could get these in black or brown, but why wouldn’t you get them in burgundy?? Burgundy is like the lost dress shoe color these days – it goes with almost every pant color (including black!) and stands out from all the drab shoes out there, but in a classy, not flamboyant, way.

That said, the color and texture of the uppers seem rather flat initially. My Clarence cap-toe brogues from Charles Tyrwhitt had a “three dimensional” appearance to the leather that I really liked. The Carter boots, on the other hand, are so smooth that they look almost plasticky.

The good news is that the leather wears very well. I’ve worn them for over six months now and  there are no creases anywhere on the leather, which is impressive. In contrast, both the Clarence brogues and the Caine oxfords from Beckett Simonon quickly developed prominent creasing (not necessary a bad thing).

Bonus: these boots are wingtips, which automatically makes you extra cool if you wear them.

The best looking part of the boots? The soles! Yep, they look super cool. They have all the “depth” that’s missing from the uppers, plus a fancy embossing.

If boots aren’t your thing, Jack Erwin has a variety of other shoes in their lineup, including oxfords, loafers, and driving shoes. I haven’t had a chance to try any of the others out yet, but if they are anything like the Carter wingtips, they will be durable and well made, if just a tad more expensive than its online peers.

Bottom line: The Carter wingtip boots, while a little pricier than offerings from Beckett Simonon or Charles Trywhitt, have classic styling and stand up very well to wear. Reasonably comfortable (some breaking in required), but heavy.

If you would like to buy any of Jack Erwin’s products, please support this site by clicking the links in this article! You can purchase the Carter wingtip boots from Jack Erwin here.

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7 thoughts on “Review: Carter Wingtip Boots by Jack Erwin”

  1. I just received my Carter boots earlier this week and love them! I have dozens of boots but wanted something dressy and sturdy to wear with both pants and jeans. They fit perfectly, both physically and style wise. I’ve shopped locally at Helm Boots in Austin where I live and feel these Jack Erwin boots compare very well with the Helm boots but at half the price. Helm boots are only available to most men outside the Austin area through online ordering so the local store really isn’t an advantage, plus I’ve learned that Jack Erwin has a storefront in NYC now. I have recommended the boots several times already!

  2. I bought a pair of Jack Erwin shoes — worst pair of dress shoe I ever had! One shoe somewhat fit the other not at all.
    Return policy is a joke —accept UNUSED items —how do yo know the shoes are of poor quality without using them at least once.
    This company is all talk no walk— save your $ J E are junk

    1. Thanks for the comments, Tony. Sorry to hear that they didn’t work out for you. Our experience has been quite good with Jack Erwin so far, and there are a lot of good reviews out there. Still, I will be posting more reviews in the future for more accurate comparisons. Cheers.

    2. Hi Tony-
      So sorry to hear you had a negative experience. Looks like our team was able to get a new pair of shoes out to you following your initial inquiry. We hope you have been enjoying the new pair, if not we’d love to discuss any ongoing issues. Please don’t hesitate to contact us at

  3. Thanks for the great review. I beg to differ, though, about wearing smooth-soled boots while riding a motorcycle due to no traction. It’s very easy to have your foot slip sideways when stopped on damp or oily pavement. The Carter boots are marketed as “combat boots,” but they are nice-looking dress boots, only worthy of combat in the corporate board room.

    I ride a motorcycle to work almost daily, and when I want a dressy pair of short wingtip boots, I have found Allen Edmonds Long Branch boot to be better. Those boots have a durable Vibram sole, unlike the Jack Erwin Carter boots.

    1. Great comment, Rick. I definitely agree, smooth soled shoes aren’t the best for traction, although I haven’t had any problems now that I’ve worn the soles down a bit. Once they wear out I will probably add some Topy soles to make them last longer and make them more grippy. I do also have a pair of Allen Edmonds boots (Cronmok) with rubber soles that are great for motorcycling to work. I’ll try to put a review up soon, so stay tuned. Thanks for reading!

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