J. Crew Oar Stripe Chelsea Boot – $149* – $298
Editor’s Note: These are all but sold out at post time, but they were seemingly popular enough that I wouldn’t be surprised if J. Crew does a re-stock. *Prices ranged from $149 during their 50% off Black Friday / Cyber Monday Sales, to full retail at $298. Since it’s J. Crew, I’m guessing most of you know that almost nobody pays full retail.
I strive to make my clothes as versatile as possible, which is why I really love Chelsea boots. A pair in black calf look killer with a well-tailored suit or black skinny jeans. Switch those out for a pair in chocolate suede and they add some texture and depth to pair well with raw denim and flannel shirts. With this flexibility in mind, I jumped at the chance to try this pair from J.Crew in their warm “burnished sienna” shade of smooth brown leather.
- Brand: J.Crew
- Style: Chelsea boot
- Last: Ludlow?
- Construction: Goodyear welted
- Leather: Vegetable-tanned, smooth-grain “Italian leather” in Burnished Sienna
- Lining: Leather, possibly pigskin
- Sole: Rubber
- Details: Black elastic gore, two-tone leather welt, contrast welt stitching, and fabric pull tabs
- Made in: China
This pair was originally ordered in mid-November when they were on sale for 35% off (~$193), but they were on backorder due to their popularity. The estimated ship date was about three weeks later and J.Crew delivered right on time. A+ for purchasing and supply chain integration!
Arriving in the standard dark grey J.Crew boot box, your new kicks come with a nice pair of cotton flannel-like shoe bags. The box itself was pretty beat up, but this really only matters if you’re a box nerd. Nothing else to write home about in here. Smells a bit like paint thinner, though.
First Impressions / Build Quality
After removing the boots from the box, my initial excitement quickly turned to disappointment.
Behold, um…. ehhhhh.
Starting with the left boot, there’s a minimal amount of wrinkly loose grain around the vamp and toe – nothing worthy of a return, but it’s noticeable. There’s a faint amount of “tiger striping” down the vamp, too. Across the toe there are a few spots where the dye bubbled up, evidently because it didn’t penetrate deep enough. Along the left side of the shaft, directly behind the elastic gore, there is a very noticeable spot the approximate size of a postage stamp where the dye was wiped off or someone tried to clean up an imperfection in the leather. The right boot has more of the same with more noticeable wrinkly loose grain, tiger striping, and spots where “burnished sienna” brown dye should be.
Spot on left boot behind the gore panel is tough to miss.
To try and quell my fears about J.Crew’s declining quality control, I ventured to my local brick and mortar store to see if the pair I received was an outlier or if other pairs had similar issues. To my dismay, the two other pairs in store (one in brown and one in sienna) had the same exact issues my pair did. Wrinkly loose grain leather, tiger striping, and a spotty dye job. Uninspiring.
Wrinkly. Quite wrinkly.
The outer leather itself is rather thin and feels quite cheap when compared against thicker hides from competitors like Frye, To Boot New York, and (my favorite) R.M. Williams. This thinness is repeated on the inside with an equally thin pigskin lining and non-removable insole. To give you a reference point, each layer is less than the thickness of a plastic credit card. There’s practically no cushioning here, so I’d wager the break-in on this pair is going to suck. Of the five reviews posted to J.Crew, only Joshua’s mentions comfort: “The break in period is rough but afterwards they are relatively comfortable.” I’ll take his word for it as comfort is subjective.
Nice gore panels with a reinforced top edge.
On a positive note, the elastic gore panels feel rather beefy and have a reinforced top edge. This means they should retain their shape for many future wears. The “Oar Stripe” fabric pull tabs are bar-tacked in place and shouldn’t rip out when you’re pulling these on before rushing out of the door in the morning. The slip-resistant rubber sole is noticeably thick and has a nice grid pattern to it for added grip. It’s not a lug sole, even though J.Crew calls it one, so I wouldn’t suggest you wear these in slick or treacherous conditions. J.Crew does not currently offer Goodyear welted resoling services, so an exact replacement would be nigh impossible.
Slim, slip resistant rubber sole.
The actual Goodyear welt stitching holding everything together is pretty flawless, which flat out shocks me. The $600 Alden boots I’m currently wearing have more stitching issues than these J.Crew Oar Stripe Chelseas do.
Fit and Sizing
J.Crew doesn’t disclose what last/form that these boots are crafted around, but they fit very similar to other J.Crew shoes I’ve purchased in the past. I’ve dubbed it the Ludlow last, as I’m pretty sure it’s also used in their Ludlow line of boots and shoes. This last has a generous forefoot with a rounded toe and tapered heel. It feels very similar to the Allen Edmonds 65 and 511 lasts.
Really nice Goodyear Welt stitching.
Sizing down to a 10 US (UK 9, EU 44) gave me the best fit out of the box. They fit very well with no noticeable heel slip or pinching. I would recommend sizing down a half size from Brannock. For reference, I am a 10.5 D/E on a Brannock device and usually take a 10D in most dress shoes, including Alden’s Barrie last. I take a 10.5E in Allen Edmonds 65 last, as that last runs narrow and I have slightly high arches. I also take an 11 in most Adidas or Nike sneakers.
Based on my personal experiences and expectations at this price point, I cannot recommend the J.Crew Oar Stripe Chelsea boots unless you can snag a pair on deep discount and feel like rolling the dice. Luckily J.Crew now offers free basic outbound shipping on all orders, but be prepared for a $7.50 return by mail fee should you not be satisfied. Personally, I have had good experiences with J.Crew’s customer support team in refunding the shipping fees, too, if there’s a problem with the actual item in question. Your mileage may vary.
If you’re in the market for a pair of high quality Chelsea boots, my recommendation always goes to R.M. Williams. Yes, they’re expensive. But their fit, comfort, materials, construction, and quality control are second to none.
About the Author: Adam Terry is a thirtysomething Technical Trainer in the heating and manufacturing industry. He enjoys bourbon, boots, raw selvedge denim, and working on maintaining his dad bod.