From left to right:
Alden for J.Crew Natural Cap Toe Jumper Boot (size 12). USA. $547. Purchase.
Oak Street Bootmakers Natural Cap Toe Trench Boot (size 13). USA. $426. Purchase.
Red Wing 9016 Beckman in Cigar Featherstone (size 12). USA. $330. Purchase.
Wolverine 1000 Mile Rugged Boot in Brown (size 12). USA. $355. Purchase.
Timberland 6 Inch Zip Earthkeepers Boot in Burnished Tan (size 13). Imported. $170. Purchase.
Bonobos Premium Denim, Flatiron Dark Rinse, Slim Straight Jeans. USA. $145. Purchase.

To preface, I’m partial to the following: a true goodyear welt for resoling and longevity, cap toes to aesthetically break the length of the shoe (I wear a Brannock size 13, but for those that run a size large I ordered down as noted above), a method for speedily donning the boots, clean edges on cut leather (as

opposed to broguing),a sole with traction since these are for NYC winter, leather lining for boot longevity & comfort, and made in the USA. It should also be noted that I’ve updated this post a few times to improve the formatting and better articulate my thoughts.


 

Alden for J.Crew Natural Cap Toe Jumper Boot

Alden for J.Crew Natural Cap Toe Boot Sole Side

General
Fits like a boot, so order a size 12 if you wear a size 13 dress shoe. Made in the USA. Since Alden offers many styles and frequently collaborates with vendors for custom runs, it can be hard to find exactly what you’re looking for. To help, here is a short list of retailers: Unionmade, Need Supply Co., Leffot, Epaulet, Leather Soul Hawaii, Winn Perry, J.Crew, Barneys NY, The Shoe Mart, Alden of Carmel.

Upper
As the name implies, natural chromexcel leather has natural variations in shade and color, but over time will patina into a beautiful golden hue. Some folks want their boots to look a certain way from day one, but with this leather the owner is a part of the final process and as the boots are worn and exposed to the elements they’ll gain character and darken into their final color. As for the style of the boot, the toe broguing is on trend, but I still prefer a simple cap toe with boots (even if broguing was born in bog boots). Other details include an abundance of eyelets and speedhooks that help to define Alden’s aesthetic refinement.
Inside, the smooth, vegetable tanned, leather lining fully covers the interior (including the tongue) and creates an incredibly comfortable boot straight out of

the box. These boots are easy to put on with a large entry area provided by the speed hooks and lack of a gusseted tongue, but with that comes a lack of protection from the elements (if it’s really pouring/snowing). The laces don’t feel all too durable, but Alden throws in an extra pair, which is a nice gesture since speed hooks frequently decrease lace longevity with their sharp edges.

Sole
Well made with a Goodyear welt featuring the highest stitches per inch in the lot. The commando (rubber) soles have an appropriate tread depth for a winter city boot to provide some traction in snow, without having to clomp around on half inch lugs. Unlike on Alden’s stacked leather soles, the lock stitching on the commando sole isn’t channeled, but since this doesn’t appear to result in any reliability issues, it’s just an OCD observation on my part.

Bottom Line
These beautifully designed and expertly crafted boots are easily my favorite of the bunch. If you have the money you won’t be disappointed when you take these out of their box.

Alden for J.Crew Natural Cap Toe Boot 1
Alden for J.Crew Natural Cap Toe Boot 4Alden for J.Crew Natural Cap Toe Boot 5
Alden for J.Crew Natural Cap Toe Boot 6Alden for J.Crew Natural Cap Toe Boot 3

 
 

Oak Street Bootmakers Cap Toe Trench Boot in Natural

Oak Street Bootmakers Natural Cap Toe Boot Sole Side

General
Very well made and true to length, however the boots are a bit wide. Made in the USA.

Upper
First read the Alden review above, since these boots are made with the same chromexcel leather and are thus a good example of the variation in color that is to be expected. Compared to the Aldens this pair of Oak Streets have a bit of a sickly hue, but they will both patina similarly, yielding to a golden hue in time. (Purely conjecture: The sickly color could be from the Chromexcel process that uses chrome salts to speed up the process, before a secondary process with natural tannins. Thus the leather has a “wet blue” phase, that since it’s never truly dyed, could be the cause of this almost blue/green tint.) Style wise the broguing is minimal, with a clean edge rather than Alden’s wavy half crescent edge, but I still find it unnecessary.
The Oak Street Trench Boot is very comfortable straight out of the box with a

calfskin vamp lining (same as Red Wing Beckman and Wolverine 1000 Mile) and well-designed tongue that lays smooth across the top of my foot and ankle. The leather laces are the perfect length for wrapping around the top of the boot, which is both stylish and a good alternative for quick lacing without using hooks, which some people don’t like due to the increased cuff damage and tripping hazard.

Sole
The Oak Street Trench is a true goodyear welt, but they have yet to release their rubber Dainite soles in the cap toe, so these are a smooth, stacked leather, waterlock sole.

Bottom Line
Oak Street makes a really nice pair of boots with top notch craftsmanship, they’re just a little wide for my foot and I wish they offered Dainite soles in this Trench style.

Oak Street Bootmakers Natural Cap Toe Boot 1Oak Street Bootmakers Natural Cap Toe Boot 3Oak Street Bootmakers Natural Cap Toe Boot 5
Oak Street Bootmakers Natural Cap Toe Boot 6Oak Street Bootmakers Natural Cap Toe Boot 4

 
 

Red Wing 9016 Beckman in Cigar Featherstone

Red Wing 9016 Beckman Cigar Featherstone Sole Side

General
The fit is typical boot sizing; one below your Brannock size. Made in the USA.

Upper
The Beckman is made with strong leather and designed with a vamp calfskin lining as well as a gusseted tongue for weather protection. Unfortunately, the tongue on my pair was made of a thin, dry, stiff piece of leather that didn’t sit flat against my foot/ankle. Thankfully, it appears to be an isolated case, as I’ve checked other Beckmans and haven’t found the problem on any other pairs. The top edge of the boot also had a thin, black rolled piece of leather trim that was stiff and felt cheap, but I’ve compared this as well, and found other Beckmans to be constructed with better, softer, leather, so again, just check what you’re getting. The laces are waxed, but too short, requiring constant restringing of the top eyelets. Thankfully that’s easily solved with a new pair of laces for under $10.

Sole
The Beckmans are made with solid Goodyear welt construction topped off with a rubber sole for snow traction. Similar to the Aldens there is no channel for the lock stitching to recess into, but also similar to the Aldens, these boots don’t have delamination issues, so it doesn’t not an issue. The insoles are vegtanned leather that’ll take a little while to conform to your foot, but should last a good long time.

Bottom Line
This can be a handsome boot, but given my anecdotal experiences with this pair of Beckmans and my Iron Rangers, I recommend double checking the quality control yourself–or better yet, buying in a store.

Red Wing 9016 Beckman Cigar Featherstone 1
Red Wing 9016 Beckman Cigar Featherstone 4Red Wing 9016 Beckman Cigar Featherstone 5
Red Wing 9016 Beckman Cigar Featherstone 6Red Wing 9016 Beckman Cigar Featherstone 3

 
 

Wolverine 1000 Mile Rugged Boot in Brown

Wolverine 1000 Mile Rugged Boot Brown Sole Side

General
Order one size smaller than your Brannock size. Made in the USA.

Upper
The burnished edges along the top are aesthetically preferable to the Beckman’s leather trim, however I’d prefer if Wolverine hadn’t embossed the leather with “1000 Mile” along the top. Some folks recommend conditioning new boots before wearing them to ensure the leather’s ready for weather, but that’s unnecessary for the 1000 Mile Boot. The leather arrives with a waxy sheen, as if the final coat of wax/oil wasn’t fully buffed off, which keeps the leather conditioned through storage and transit. Because of this the leather is very soft and water repellent from the get go, as well as very comfortable. Similar to the

Oak Street Trench and Red Wing Beckman, the vamp on the 1000 mile is lined with calfskin. To top them off, the laces are waxed, the perfect length, and a good color. The eyelets are an antiqued brass, which is also my color of choice.

Sole
Traditional goodyear welt construction with channeled sole stitching to prevent premature wear. The 1000 Mile outsole is made with stacked leather as is the heel, which is then finished with a piece of rubber for slip resistance.

Bottom Line
These are solid boots that can be made even better by your cobbler with the addition of some half soles for winter.

Wolverine 1000 Mile Rugged Boot Brown 1
Wolverine 1000 Mile Rugged Boot Brown 4Wolverine 1000 Mile Rugged Boot Brown 5
Wolverine 1000 Mile Rugged Boot Brown 6Wolverine 1000 Mile Rugged Boot Brown 3

 
 

Timberland 6 Inch Zip Earthkeepers Boot in Burnished Tan

Timberland Earthkeeper Zip Burnished Tan Sole Side

General
True Brannock size. Choosing to use leather from a “Silver Rated Tannery”, recycled plastic, recycled rubber, and organic cotton laces is commendable. Made in China.

Upper
The best thing about these Earthkeepers boots is the excellent color of the Burnished Tan leather. Unfortunately, the interior is lined with a synthetic fabric that wears out much faster than one made of leather, which ultimately renders the boot uncomfortable and destined for landfill. Additionally, the structure of the heel cup and toe box is made of plastic since the leather is too thin to hold the shape on it’s own. The toes are also unnecessarily long and the burnishing on this specific pair (but not all) was poorly done with a very rigid and unnatural cutoff point where the plastic toe box ended.

Sole
Not a true goodyear welt, but they channel the sole stitching and the shoes are comfortable. If the liner does last the soles are very thin, so resoling can be problematic (I’ve tried in the past, but it was unclear if it was an impossible task or the cobbler botched the job).

Bottom Line
Given the other boots will last much longer if well cared for with basic maintenance (periodic saddle soap + Obenauf’s) these are cheaper in the short term, but more expensive over time.

Timberland Earthkeeper Zip Burnished Tan 1
Timberland Earthkeeper Zip Burnished Tan 4Inside Toe & Heel
Timberland Earthkeeper Zip Burnished Tan 6Timberland Earthkeeper Zip Burnished Tan 3

 

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