Oak Street Bootmakers

[Oldtimer]

How snug were the penny mocs when you first got them? OSB recommends full size down, so that’s what I ordered, but they feel *cramped*.

@shahtirthak Awesome collection! Seems like you are to OSB what @audog is to Grant Stone

Brand new Penny Moc in Natural CXL

Try as I might, I just can't wear heeled footwear casually with shorts. I love my Grant Stone Travellers, but being new to both mocs and pennies, I'm opting for a more conservative look with the flat camp sole.

These are a lot darker than I expected, and I'm chuffed to bits that they are! I almost thought I'd been sent a brown pair at first. I went a full size down from my usual 10 in a sneaker to a 9 and they are snug, but not uncomfortably so. It was definitely the right choice. I know by all accounts they'll stretch a lot, so I expect they'll get more comfortable over the next few weeks.

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No affiliation, but I have to give a plug to Cameron O who filmed the only review currently in existence for this offering from OSB. His video is what ultimately pushed me to get these.

 

[Commisar]

How snug were the penny mocs when you first got them? OSB recommends full size down, so that’s what I ordered, but they feel *cramped*.

I only have experience with Rancourt for unlined CXL penny loafers on the 114 last but for that last 1/2 size under brannock is a ok.

For oak street on the 800 last I've read 1/2 or 1 under brannock

 

[Commisar]

Oakstreet Natty CXL Boots after many years of use and minimal care. Still going strong.

Natty cxl turns brown 🟤

@shahtirthak Awesome collection! Seems like you are to OSB what @audog is to Grant Stone

Brand new Penny Moc in Natural CXL

Try as I might, I just can't wear heeled footwear casually with shorts. I love my Grant Stone Travellers, but being new to both mocs and pennies, I'm opting for a more conservative look with the flat camp sole.

These are a lot darker than I expected, and I'm chuffed to bits that they are! I almost thought I'd been sent a brown pair at first. I went a full size down from my usual 10 in a sneaker to a 9 and they are snug, but not uncomfortably so. It was definitely the right choice. I know by all accounts they'll stretch a lot, so I expect they'll get more comfortable over the next few weeks.

View attachment 2069251
View attachment 2069289

No affiliation, but I have to give a plug to Cameron O who filmed the only review currently in existence for this offering from OSB. His video is what ultimately pushed me to get these.

I'll be looking at a brown CXL beefroll pair this summer

 

[PeterHH2024]

Hi guys,

Im looking at a pair of field boots. I am approximately a size US7.5EE in Red Wing Chukka, and roughly a US7 in New Balance sneakers and about a 7 in Viberg on their big 1035 last. My feet are not that long, and quite wide.

Can anyone help me if OSB field boots could be right for me?

 

[NewDenimBootHead]

Hi guys,

Im looking at a pair of field boots. I am approximately a size US7.5EE in Red Wing Chukka, and roughly a US7 in New Balance sneakers and about a 7 in Viberg on their big 1035 last. My feet are not that long, and quite wide.

Can anyone help me if OSB field boots could be right for me?

I have four pairs of Oak Streets, and highly recommend them. The company has an amazing customer service person named Hayley, and I asked her about sizing with my first pair. I also have wide feet. Send your question to: [email protected]

 

[steadystate]

How snug were the penny mocs when you first got them? OSB recommends full size down, so that’s what I ordered, but they feel *cramped*.

Wow, I didn't get any notification for this. Hope this is still relevant, but I did indeed go a full size down and they were pretty snug at first, and stretched just like OSB said they would. I got blisters at first (because I never seem to learn, and decided to walk for an hour and a half in them first time) but now they're super comfortable. Probably my most worn summer shoe this year.

The link I posted on the previous page to Cameron O's review sums up my own experience almost identically.

 

[Oldtimer]

Wow, I didn't get any notification for this. Hope this is still relevant, but I did indeed go a full size down and they were pretty snug at first, and stretched just like OSB said they would. I got blisters at first (because I never seem to learn, and decided to walk for an hour and a half in them first time) but now they're super comfortable. Probably my most worn summer shoe this year.

The link I posted on the previous page to Cameron O's review sums up my own experience almost identically.

Thanks for the reply! How long was the break in? I’ve had mine since for a few months now and worn 10-12 times with minimal stretch so far

 

[steadystate]

Thanks for the reply! How long was the break in? I’ve had mine since for a few months now and worn 10-12 times with minimal stretch so far

Only a few weeks. It happened pretty quickly.