Oak Street Bootmakers Trench Bootsearch

Oak Street Bootmakers Trench Boot

Oak Street Bootmakers Trench Boot

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Make a cordovan drop and I’m in
any word on whether this drop would be coming back anytime soon?
I got lucky on my sizing. Already had a pair of 7.5 Iron Rangers and picked 8 for the Trench Boot. Only took a couple of wears to break them in and now the feel plenty comfortable.
My boots arrived yesterday, was very excited to open the box. Unfortunately I find they did not come with the dainite sole that I ordered. Pretty disappointed. Hopefully they can sort this out.
I purchased these in brown with Dainite soles. They arrived with a few dents, for lack of a better term, on the toe of the left boot. Overall they’re very nice though. I’ll answer my own question posted before I purchased in case anyone else is looking for sizing info. I’m a 13 in Red Wings and Wolverines. I bought these in a 13 and they are tighter than my other boots. Oak Street recommends a snug fit though so they’ll stretch to your foot, so I’m hoping that happens with break in. Here are some photos of the left toe. It’s kind of hard to see in the picture, but these marks are indented.

Got the #8 daintite in a 9.5 and should have gone for the 10. Here’s to hoping that cxl will stretch a bit.
I have a couple pairs of OSB boots and a pair of their penny loafers. All are CXL, and they all started out a bit snug but after a dozen or so wears (full days) the leather started to relax and stretch a bit. They all fit great now.
Received my boots earlier today, a pair of #8 dianite cap toe, a few small blemishes but nothing major.

Wish they offered custom widths i have widefeet and I tend size up a bit to accommodate, so i have definitely more than the preferred 1/2" of room in the toe at at least an inch.

Wish i didn't have to choose between nice tight lace with comfortable width in expense to excessive dead space in the length.

Don't think I'll be too disappointed in them as a whole though, definitely liking them so far and cant wait till they're broken in.
Very Tom Joad.
Just got my #8's. Little more rounded toe than I was expecting/prefer. Fits great. Few scuff marks that should buff out.


Just received my Black 11.5 Dianite Trench Boots! They fit like a glove, look great and feel even better!! I'm usually a 12 boot in most brands. Only bought one this last drop as I wanted to learn the fit. Now that I know, bring on the next drop!
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I think when Oak Street says true to size, they are spot on. Other boots have me sizing up by 1/2.
Haha. Can you tell? Looking forward to taking them out for a day for the true test.
Well if there are any size 11 cap toe dainites in natural that don't fit let me know ;)
Just received my FedEx shipping notification! Fingers crossed that they fit correctly.
If you went a half size down when ordering it'll fit you like a glove. I wear sneakers in US8 and bought a 7.5 direct from Oak Street and they fit perfectly. Can't wait for my second pair from this order!
I have a pair of OSB wingtips in 9 and I called OSB to ask what size I should purchase in the trench boot. David from OSB said that I would go up a half size as the trench boot fits differently than the wingtip. Your statement about a half size down seems spot on as I usually wear a size ten in running shoes. Thanks for the tip.
Well i guess they're delayed
Why am I not surprised lol
Confirmation of delay by mail received this morning...