J.Crew MacAlister Boot: An Impressive Chukka Hiding in Plain Sight

If you’ve ever been into one of J.Crew’s legacy stores — meaning the ones in malls, not the standalone men’s shops in New York — you know how they’re laid out. The footwear, for example, is clustered on a rack near the rear of the store. As expected, there’s a mix of Red Wing and Sperry boots and shoes and the occasional off-brand sneaker you’ve never heard of before. Hidden between these models, though, are a few boots J.Crew actually makes itself — like the MacAlister Boots.

Details on where or how these boots are made are sparse, to be honest, besides the suspiciously simple “Made in Italy” tagline stamped into the leather insole, but because J.Crew isn’t necessarily known for its boots (despite making several solid pairs), it doesn’t need to say much more.

The boots, however, have long been a hot topic on Reddit pages where users discuss the finer details of menswear, and round up the best deals. When the boot dips below $100, hundreds of users are fast to flag them, saying they’re about as good as Clarks Desert Boots but far cheaper. That being said, are they? And, how can J.Crew sell a solid boot for so cheap? We found out.

J.Crew MacAlister Boot: What We Think

For the price, given you get these on sale, there are few leather chukka boots better than J.Crew’s MacAlister Boots. Based on a style popularized in the early 20th century, the two-eyelet, ankle-height design doesn’t need long to be broken in and offers a comfortable step from the start, thanks to rubberized, albeit thin, crepe sole.

The textured leather iteration was easy to wear, whether with chinos or shorts, like Wooden Sleepers founder Brian Davis suggests, and they never felt too dressed up like other leather boots can. For the money, these are a must-buy, even in spite of J.Crew’s lackluster legacy in footwear design.

J Crew

J.Crew MacAlister Boots

• $168.00 at J Crew

J.Crew MacAlister Boot: Testing Notes

They’re flattering without being too narrow in the toe box.

While I love the Clarks Desert Boot, my primary complaint has always been that they’re far too, well, bulbous. The toe box is big and circular, like a lightbulb, but the arch cuts in deep, creating a kind of clown shoe-like shape.

With J.Crew’s MacAlister Boot, the above angle is far more straight, with far less rounding, despite being equally as room, if not more so, in the toe box. For wide feet, which I have, these are a dream, even if they feel pretty pared back.

Evan Malachosky

The unlined leather uppers are easy to break in, and the lined heel counter helps preserve your socks.

True leather boots are stiff, often because of the quality of the leather, but also leather liners, which are generally made from the same material as the outer boot, both to make the shafts taller and more able to stand on their own but also smooth. They mold to your feet with time — but never immediately, of course.

J.Crew’s textured leather MacAlister Boots come unlined, save for the leather insole and the leather-accented heel counter. While the absence of a liner makes these a little flimsy, the lined heel helps prevent blisters but also preserves your socks, which would otherwise rub against the raw leather inside.

The crepe soles are unexpectedly thin.

Reviewers are quick to draw comparisons to the Clarks Desert Boot, another suede or leather chukka boot with origins in the European military. The Clarks boots, though, with thick, yellow-ish crepe soles, are famously squishy, like walking on rubber clouds. The MacAlister boots, on the other hand, have crepe soles, too, but they’re far thinner, a feature that lends a lower profile and better foot-to-ground feeling, but also less, well, squish.

You’ll feel the rocky terrain beneath you: the unstable gravel, the mounds on sidewalk ramps and so on and so forth, but they won’t punch through the crepe, per se.

Evan Malachosky

They’re almost always on sale.

Jump onto J.Crew’s site on any given day and you’re bound to run into banners that read, “Take __% off full-price items,” or “Take an extra __% off sale items.” Brands this big always need to shed extra inventory, and their boots likely move much slower than sweaters and chinos, for example, two styles the brand is better known for.

They clump their footwear options into the sales to entice would-be shoppers, and it often works. Wait for a sale — it’s worth it. If there isn’t one going on right now, there will probably be one next week.

The textured leather shows its scuffs.

All leather ages, but textured leathers like roughout do so more obviously. I, for example, stubbed my toe on a cement bench and left a visible line running up the toe of my boots. This isn’t a bad thing, per se, just something to take note of before buying, especially if you’re especially particular about how your shoes look.

Evan Malachosky

They feel a little loose, even when you order your true size.

Although it’s likely just me adjusting to an unlined boot versus a lined one, I felt the J.Crew MacAlister Boots felt big, even though my toes sit exactly where they’re supposed to be. The super-casual nature of the design leaves the wearer feeling a little, well, unchained inside these, which is good if you want a comfortable boot to sit at a desk in, but can be a little unnerving if you’re doing a lot of walking.

All in all, though, the fit change with the socks I chose: the boots felt better when I wore thicker socks.

J Crew

J.Crew MacAlister Boots

• $168.00 at J Crew

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