Long Term Review, Stitched Footwear, TB Phelps

T.B. Phelps Weekender: A Different Take on a Classic

Price: $260

Why Buy?

The T.B. Phelps Weekender offers a surprisingly comfortable and supportive option in the chukka market, and tops it off with high quality and interesting materials.

Why Stay Away?

The T.B. Phelps Weekender in elk has different characteristics in how the leather develops, and may not be for everyone.


Height5 Inch
MaterialElkskin and Bison Upper / Rubber Outsole
Weight550 g / 1 lb 3.4 oz
Country of OriginDominican Republic


Disclaimer: TB Phelps provided these shoes at no cost for review, however, this had no impact on the thoughts below. TB Phelps was not given the opportunity to review, edit, or change the content.


TB Phelps WEekender
T.B. Phelps Weekender

100wears first took a look at the T.B. Phelps Weekender back in July. I’d encourage you to take a look at that review before reading this one, but in short – from initial impressions, it seemed like the Weekender used some great materials, but opted for a few things that I wasn’t sure were going to hold up in the long term.

This pair have now been worn around 100 times, and have seen more than 100 miles. They really have seen it all, from nice sunny days, to being absolutely soaked through and mud caked after being caught in a hurricane. How did they hold up? Let’s dive in.


By the way, if you’ve never heard of T.B. Phelps before, they offer a variety of products in some really interesting leathers. Things like sheepskin, deerskin, elkskin, and more. You can read a full history of the brand on their website.



TB Phelps Weekender
T.B. Phelps Weekender

In the initial impressions post, I felt that the T.B. Phelps Weekender leaned heavily into the rustic side of the equation, and after wearing them this is doubly true. The thick thread, and hand-cut design obviously still remain, but the edges of the leather have started to see some fraying. Not enough to cause any durability concern, but pushing this shoe even further into the casual end of the spectrum.

The leather itself held up remarkably well, with one notable exception. It didn’t really even start to show any creases until well past 75 wears. I kind of wish there was a little bit more wear, actually. One of the big draws on non-standard leathers is how they change and develop. It might be worth doing another update on these at 200 wears.

Inside there isn’t anything to update on. Apart from some creasing, there really isn’t any difference when compared to new.

TB Phelps Twist
A bit of twist

The only major complaint that I had with the upper is that on the right shoe there was some twist in of the materials. It was almost as if one quarter shrunk while the other stretched. I’d never seen this happen before, but with non-standard materials you can get some non-standard behavior.


As for the back stay, other than moving with the rest of the upper on the right shoe, the still looks nearly new.

Mid- and Outsole:

TB Phelps Weekender outsole
Outsole – other than some staining, almost no wear; Leather – a lot better than I execpted

The outsole on the T.B. Phelps Weekender ended up being way more durable than I expected, in nearly every way. I’ve worn just about every campsole you can think of – Amazonas, Vibram, Rancourt-branded, Oak Street Bootmakers-branded, etc. This might just be the most durable. Even after more than 100 miles, the stars can still be seen under the ball of the foot. There has been a little bit of staining and discoloration, but that is fairly typical of a black rubber camp sole.

The part of the shoe I was most interested in was tracking was the piece of leather on the cut out of the midsole. It isn’t the standard stacked leather outsole, which is multiple layers thick and treated to prioritize durability over comfort. Instead, it’s the same bison material as the backstay. I thought that there was no way this was going to stand up over time.

I can say, with certainty, that I was incorrect. While it doesn’t look great anymore – it’s absorbed a lot of water – it has held up as well as can be expected for something on the bottom of a shoe.

Fit & Comfort:


TB Phelps Toebox
Slightly collapsing toe box

The T.B. Phelps Weekender is built on their Michael last. It fits slightly narrow and slightly long, especially compared to other handsewns. I measure an 11.75 D on the brannock, and ordered these in a size 12 – my normal “go to” size for a last I’ve never tried. This was definitely the right choice.


For reference, I wear an 11.5 in Quoddy, 12 in Rancourt, and a 13 in most Nike sneakers. For a full list of every shoe reviewed on 100wears, click here.

I found that the Weekender in elk didn’t stretch much, but they did collapse a bit. In other words, if you’re issue is just width and you have some space above your foot and/or toes, you’ll be OK, but if you need more volume I would definitely size up. You won’t get it from stretching like in other handsewns.

T.B. Phelps does offer free returns if the shoes are unworn, so you should be able to swap pretty easily without much hassle if you order the wrong size initially.


TB Phelps Lining
Plush interior lining and tounge

The T.B. Phelps Weekender is definitely one of the most comfortable handsewns I’ve ever worn. The shoe is heavily padded throughout – both underfoot and on the upper. As I’ve mentioned elsewhere, I injured my foot over the summer, and this was one of only 2 handsewns I could wear for several months afterwards.

Even with the structure breaking down a bit with wear, they are still very supportive. The addition of the shank in the outsole goes a really long way here.


There is really only two things to be aware of on the comfort front. First, these things run HOT. After the initial review, I wasn’t able to wear them until September because they baked my feet. Of course, the opposite side of that coin is that they are nice now that we are in the winter months.

The other is that, because of the twisting of the upper, the tongue on the right shoe regularly slides to the side unless you really yank on the laces. It isn’t the end of the world, but if you experience the same you might want to plan on a trip to the cobbler to tack the tongue down.  

Materials & Construction:


TB Phelps Elk
Edges on the leather getting a bit more raw

The materials are really the star of the show here. The elkskin upper looks and feels different than most other handsewns, and the bison leather backstay is even more unique. Inside, they used a cowhide lining.

T.B. Phelps chose pretty thick cuts of each on the Weekender (total thickness of the upper is around 4 mm), which is probably why the shoe is so supportive. If you’re interested in hearing more about why they picked the leather, T.B. Phelps has a blog post about it here.

You should know that this type of leather does show small abrasions fairly easily. To me, that’s a feature, not a bug, but if you’re used to calf shoes this is something you should know about.


As mentioned above, the rubber used on the outsole is incredibly durable. It also includes a shank inside the little leather section, something almost unheard of in handsewn style shoes.


TB Phelps Weekender Wear
Almost no wear on the outsole

The T.B. Phelps Weekender is held together with Blake Stitch Construction. You can read a bit more about that here, but in short, the upper is folded around the shape of the last and the outsole is stitched directly to it. This style of shoe is generally the most flexible and lightest weight, but can be a bit less waterproof and requires special machinery to resole.

Ease of Care:

Elkskin conditioner
Lots of pores there to absorb conditioner

As mentioned in the previous review, elk skin requires a bit more attention than typical cowhide found on most shoes. It absorbs more conditioner, so it’s fairly easy to over condition, and at the same time it loses it a bit faster as well, so it’s easy to let the leather get too dry. This is doubly true of the shoe gets soaked through.

The good news is that if you have any experience with higher-end footwear, all the tell-tales are there. If it feels dry, give it more. In the 6ish month’s I’ve used these, I conditioned them once with Obenauf’s Heavy Duty Conditioner, right after they were soaked through. Others will say you’re OK using more standard conditioners such as Bick 4 or Venetian Shoe Cream, but with such porous leather it is easy to over-condition elkskin using those products.

I actually didn’t use shoe trees in these for most of their life (sorry T.B. Phelps!). I wanted to lean into the rustic vibe, and thought having them break down in structure a little bit would help get them there. Personally, I like the outcome, but it wouldn’t hurt to use trees if you wanted to keep them newer looking longer.


As always with Blake Stitched shoes, not every cobbler has the machine to replace the sole on these. If you do plan on adding a new sole down the line, expect it to cost a bit more than a goodyear welt.

Pricing & Value:

Elkskin Shoe
The Evolution of Elkskin


T.B. Phelps has the Weekender at $260 on their website. You can find them at other places, but the pricing seems to be fairly consistent. If you’re looking to pick up a pair, you can save 10% by signing up to their newsletter.

This price point puts them in a bit of a no-mans-land. There are the typical LL Bean, Sperry, and Sebago options which are made with cheaper materials for a lower cost. And, most of the typical Maine handsewn makers offer a pair of Chukkas, but they are mostly around $100 more.

It’s also really hard to find interesting leathers at any of those places. For that, you generally need to go to a brand like Yuketen – which bumps the price even higher.


I hate to keep going back to it, but the materials on these shoes really make them a unique value proposition. Ever since the internet made various microbrands viable, most of the leathers that were interesting a decade or so ago have become fairly standard – if you want a pair of shoes in brown Chromexcel, you probably have them. Same thing with a natural Veg-Tanned cowhide, Horse Hide, or something in Waxed Flesh.

T.B. Phelps is offering something even more interesting, and if that appeals to you, there really isn’t that many other places to go at any price.

Wrap Up:

T.B. Phelps Weekender
T.B. Phelps Weekender

When I first took a look at these shoes, I found a surprisingly comfortable and supportive take on a classic design. I liked the new materials, but worried about the durability a bit. After lacing them up more than 100 times, I found that the durability concerns were completely unfounded.

The shoes are not 100% perfect – I do wish they did not twist, and I still feel that upgrading the laces would go a long way in improving the total product. That being said, I am glad that T.B. Phelps is coming into the market with something interesting. I think that there are a lot of people who have a hole in their closet that the Weekender could fill.

If you’re thinking they might be right for you, it’s definitely worth picking up a pair.

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