"Could use a few more customization choices"
It works fine, but I kept wishing there were more little options to tweak. Even simple things like changing small layout details or having a few extra style choices would’ve made it feel less basic. As it is, it’s straightforward, maybe a little too straightforward for what I was hoping for.
hello_curtis651
May 22, 2026
"Wish I’d picked something that lasted longer"
I had these boots for about a year, i regret spending the money on them. They looked nice and felt really comfortable at first, so I thought I’d made a good choice. But the sole wore down way faster than I expected, and then the stitching started coming loose. For the price, I really thought they’d hold up better over time.
RobertMerchant
May 21, 2026
"Return process was all over the place"
I tried to do an exchange, but it just never actually happened. First I was told one thing, then I was waiting around, and the whole return process felt kind of messy. I just wanted to swap the item, not spend a bunch of time chasing it down. Frustrating overall...
"Absolutely no arch support"
I’m annoyed I wasted money on these. After just a short walk, my feet were already hurting because there’s basically zero arch support. I don’t know who thought these were comfortable, but they definitely missed the mark...
Kent.rosario
May 11, 2026
"Looked good, but the leather felt cheap"
They looked nice right out of the box, so I was hopeful, but the leather felt thinner than I expected and started creasing quickly. For what I paid, I thought they’d feel a lot more solid. They’re not awful, but it had that kind of “now this is my problem” feeling, which was frustrating. Overall, just a bit disappointing...
michael.Dismukes
May 06, 2026
"Nice boots, but, the price feels a little steep"
I ordered from Oak Street Bootmakers after browsing around for a while, and overall, the boots are definitely nice. They feel sturdy, well made, and, i don’t have any real complaints about the quality itself.
The main thing for me is the price. I understand they’re a step up from cheaper boots, and you can tell some care went into them, but, even then, it’s a little hard to justify unless they’re on sale, or you’re really set on this specific style.
Shipping was fine, the website was easy enough to use, and nothing really went wrong. I’d say it’s a solid product, but, because of the pricing, it lands more around 3 stars for me.
"Decent boots, but sizing seems inconsistent"
I bought the same size I usually get, i’m not totally sure what to think. One pair fit well, but the other felt noticeably tight. The boots themselves seem okay and I do like them enough, I guess, but the sizing left me a bit confused.
"The leather didn’t feel quite right to me"
The boots looked nice when I got them, but personally, the leather just felt a bit fake to me. Maybe others won’t mind, but it wasn’t quite what I was expecting
James_cook94
April 23, 2026
"Shipping felt like it took forever"
I’m giving this 1 star because the shipping was really frustrating. I kept checking for updates and it felt like my order was just stuck somewhere, which made me feel kind of trapped waiting around with no real idea when it would actually show up.
The boots might be totally fine, but by the time they arrived, the long wait had already ruined the excitement for me. I don’t think I’d order again unless they seriously improve the shipping process.
JustinCruz_77
April 22, 2026
"From what I remember, the updates weren’t great"
The boots themselves seem fine so far, but looking back, the communication wasn’t the best. I remember the updates being slow, and when they did come through, they weren’t always very clear. It just made the whole experience feel a bit more frustrating than it needed to be
RobertArmstrong
April 21, 2026
"Order processing took way longer than expected"
I felt like I was waiting forever just for my order to process. I reached out to support and they basically said something like, “It’s still being reviewed, please give it a little more time,” but it ended up taking way longer than I expected. Frustrating experience overall.
JulieCarranza
April 07, 2026
"Refund has been a pain"
I sent my boots back and the return itself seemed straightforward at first. The tracking showed they got there, so I figured the refund would just happen, but nope, I ended up having to email more than once just to get any kind of update.
The replies were polite, I guess, but also slow and didn’t really tell me much. I understand refunds can take a bit, and part of me thinks maybe it was just bad timing, but it was still really frustrating. I liked the boots enough, weirdly, but after this I don’t think I’d order again
hello_jo896
March 23, 2026
"Really well packed, just a little messy inside"
The boots showed up in really good shape, so I was happy about that right away. The outer box felt sturdy and it didn’t look like it had been crushed or tossed around too badly during shipping, which is always my main concern with shoes because scuffs can happen so easily. The boots themselves were totally fine and didn’t have any marks or damage. The only small thing I noticed was that the tissue paper inside was kind of messy and bunched up, like it had shifted around in the box, but that’s not a huge deal since it’s just packaging. Overall, everything arrived safely and I’m happy with how it was packed.
hello_kyle585
March 11, 2026
"Break-in was much rougher than I expected"
I really wanted to like these, and the leather does feel sturdy and well made. But the break-in period was brutal. I wore them around the house and on short walks for a couple of weeks, and I was still getting heel rubs and blisters. For the price, I expected them to be a little stiff at first, but I did not expect this much discomfort. I am not sure I would buy them again.
denisegoodell4973
March 09, 2026
"Cute boots, but where’s my size?"
I really like these boots, but every time I check, my size is out of stock. Like, of course the one pair I actually want is never available. They look great, and I’d probably buy them right away if I could, but I keep ending up disappointed.
david.Hopping
March 06, 2026
"Hard to shop and too much waiting"
I gave up trying to use oakstreetbootmakers.com after a while. The pages were slow, the menus were confusing, and I kept feeling like I was stuck waiting in a queue just to get anywhere. I couldn’t find the exact boot style I wanted without clicking around way too much.
The product pages were also messy on my phone. Photos loaded strangely, checkout didn’t feel smooth, and the whole thing just got frustrating fast. For boots at these prices, I’d expect the site to be much easier to shop...
PaulineBeauvais
March 03, 2026
"Still no reply"
I emailed them twice about my order and never heard back. Not even a quick update. Frustrating, honestly. Feels like customers just get ignored.
michael1978
March 02, 2026
"Looked like the photos, but I had my doubts"
The boots mostly looked like the pictures, though the color was a little darker in person. I was kind of suspicious at first because you never really know with product photos, but overall they matched well...
james1973
February 23, 2026
"Not as resoleable as I expected"
I bought these thinking they’d be easy to resole, but when I took them to a cobbler, they basically said it wasn’t worth the hassle. That was disappointing, and the next steps weren’t clear at all. I wasn’t sure if I should try another cobbler, contact the company, or just give up on them.
marcella_Hildebrant00
February 21, 2026
"Not the brown I was expecting"
I was really looking forward to these boots because the photos made them look like a nice dark brown. When the box showed up and I opened it, the color was the first thing I noticed. They looked more reddish-orange than brown, which was not what I thought I was buying. For the price, I figured the color would at least be close to the pictures, so it was a letdown.