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J.Crew MacAlister Desert Boots in Leather – $168

NOTE: These are sold out at post time, but they’re one of those items J. Crew has made for years and years. So one would think it’s a temporary stock issue, and they’ll be back at some point either in leather, suede, or in both options. 

About the Author: Adam Terry is a 30-year-old Technical Trainer in the heating and manufacturing industry. He’s #menswear by day and #workwear by night. He enjoys raw selvedge denim, Scotch whisky, and working on maintaining his dad bod.

Polos, chinos, and chukka boots. This Dappered Style Scenario favorite is a simple, yet stylish outfit that’s perfectly timed for Spring and Summer weather. One core tenet of that aesthetic is a versatile pair of chukka or desert boots that can be deployed into action in various situations – from casual weekend wear to modern “smart casual” office dress codes. Today we’re looking at J.Crew’s perennial favorites, the MacAlister boots in a wonderfully textured leather.

The MacAlister leather chukka bringing all the texture.

The Adam Review Scale of Excellence (A.R.S.E.)

  • 5 – Excellent! No issues and highly recommended.
  • 4 – Good. Above average, but not perfect.
  • 3 – Average. Minor issues, might be good at the right price.
  • 2 – Fair. Below average due to defects, flaws, or imperfections.
  • 1 – Poor. Significant issues, not worth purchasing at any price.


  • Brand: J.Crew
  • Style: Desert/Chukka boots
  • Size: 11 US (44 EU)
  • Last: N/A
  • Construction: Stitchdown
  • Upper: English leather
  • Sole: Crepe rubber
  • Details: Leather sockliner
  • Extras: N/A
  • Country of Origin: Italy
  • Price: $168 USD

The leather can be scarred creating character and depth best for casual wear.


My pair of MacAlisters were ordered on a Monday afternoon, shipped out on Friday afternoon, and were delivered on Sunday afternoon via UPS SurePost. As someone who works in sales, I understand that global logistics are a nightmare for most companies right now, but most companies can get stuff shipped out within a day or two after receiving an order. These boots sat in a J.Crew warehouse in Lynchburg, VA for almost a full week before leaving the dock.

FYI: J.Crew’s standard 30-day return policy applies here, so you’ll have a full month to think about your purchase before deciding on a return. They no longer offer exchanges. As always, shoes need to be unworn to be returned successfully. Note – J.Crew will deduct a $7.50 fee if you decide to use their return label. This can be avoided if you return to a retail store near you.

Score: 3/5 Stars – Slower than average shipping and online returns are not free.

The unboxing is nothing to write home about, but the boots are solid.


This pair arrived in a MacAlister-specific box with minimal branding in a military aesthetic. Unfortunately, the shoes inside were not wrapped with anything other than a sheet of tissue paper (effectively the size of one square of single-ply toilet paper). This meant that the shoes accumulated a few scrapes during shipping that are apparent in the unique leather finish. For some, this adds some character. Given a shoe brush and a few minutes worth of elbow grease, these scratches can buff out. There were no accessories or other items in the box to note.

Score: 3/5 Stars – The unboxing experience was less than ideal, but the boots are solid.

First Impressions

Fresh out of the box, you’ll notice that the leather is super interesting. If you’ve ever seen crazy horse leather or C.F. Stead’s Waxy Commander, this leather is very similar. It’s definitely geared towards a rough and rugged aesthetic with tons of character. As noted earlier, there were some scratches in the leather when I pulled them from the box. Most of these are small marks where one boot scraped across the other when the UPS truck probably jumped a speed bump at 50 MPH; most of these marks are superficial and don’t really detract from the overall look and feel. Do note that if you’re looking for a dressier chukka boot, these are not the best choice for that position as these will show more character and depth as they earn their battle scars.

An interesting leather that is rough, rugged, and full of character.

The MacAlister boots are classic desert chukka boots in that they have a simple, two-eyelet leather upper that’s directly stitched down to a natural crepe rubber outsole. J.Crew has their boots made in Italy (possibly by the Astorflex factory, but you didn’t hear that from me). Those Italian cobblers love leather and you can see that here, too, when you look at the simple construction that puts the upper leather front and center. These are unlined, too! For what’s there, the stitching is neat and tidy with no noticeable errors. The perimeter stitchdown sole stitching is chunky and basic, running about four stitches per inch. It’s neatly finished, though.

All stitching, both small and chunky, is neat and tidy.

Style wise, chukka boots are fairly versatile and can be paired with lots of style options, depending on how the specific boots are cut and constructed. This pair of MacAlisters was designed to lean more casual, pairing best with casual chinos or comfortable denim. Take a look through the Style Scenario archives to get a feel for the polo and chinos aesthetic, which takes advantage of dressing up some desert boots or chukkas and making them office friendly.

No arch support, but the leather sockliner and crepe sole add to the comfort.

Unlacing the flat, braided cotton laces unearths the barely there internals of these boots. As mentioned earlier, these boots are unlined except for a buttery soft sockliner/footbed. The footbed piece has some decent cushioning underneath for some initial comfort, but don’t be surprised if your feet start hurting after a few hours. There really is no arch support with these.

A good quality, thick crepe rubber sole on par with Clark’s Original Desert Boots.

Natural crepe rubber is one of nature’s wonders and while plenty of brands use crepe rubber soles for their shoes, there can be a difference from one brand to the other in terms of quality. I find that the soles on these boots are similar to the Clark’s Originals Desert Boots – good quality, better than average, but not as thick or squishy as higher tier, premium brands.

Score: 4/5 Stars – Overall above average, solid boots with decent craftsmanship.


In terms of sizing, I recommend trying your true-to-size Brannock measurement. I tried this pair in 11 US, as my usual size of 10.5 was sold out. This particular pair feels a bit roomy, even with thicker socks, so I’d stick with your true-to-size measurement to start.

Fit wise, the toe box is roomy with enough open space to comfortably splay out, even on warmer days where you might need some extra room. There’s also enough vertical space where you won’t feel like your feet are trapped in a toaster slot. The heel is slightly smaller, but not enough to cause any discomfort, and I noticed no measurable heel slip with the laces cinched down. Desert boots like these are meant to be slightly loose and forgiving, so even those of you who need a slightly wider width may feel like they’ve found a winner here.

Accommodating toe shape should work for both average and slightly wider widths.

For size reference, I am a 10.5 D/E on a Brannock device and usually take a 10 D in most roomy dress shoes, including Alden’s Barrie last and Grant Stone’s Leo last. I take a 10.5 E in Allen Edmonds 65 last, as that last runs too narrow for me. I also take a 10.5 in Converse/Vans and an 11 in most Adidas/Nike/Jordan/Yeezy sneakers. Have a size question? Email us!

Comfort is always subjective, but I find desert boots like these to be fairly comfortable out of the box. The soft leather sockliner/footbed, crepe sole, and loose nature build in a bit of comfort. However, these shoes have little to no arch support so I do get tired of them quickly.

Score: 4/5 Stars – Fits true to size; comfort is OK, although I’d like some arch support.

Final Thoughts

All in all, I do like these MacAlister desert chukka boots. While they might look a little rough around the edges and their score on paper is lower than what you’d expect, I think that’s part of their charm. For many of you out there, you’re looking for something less polished that can be worn in a lot of casual style situations. These may be exactly what you’re searching for.

If you’re in the market for these boots, try and hold out for one of the regular 20-40% off sales. That will drop the cost down significantly and position these at a better value for your dollars. At that point, I think these are a better purchase than pairs from Clarks, Amazon, or Target. At full retail, I think you’re better served with Huckberry’s fantastic Rhodes Tyler chukkas. Cheers!

Avg. Score: 3.5/5 – Boots are decent, but logistics and subpar packaging lower the score.

A decent boot for casual looks.


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