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.

 

[Commisar]

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.

The Penny Loafer is on the 555 last.

Unlined cxl will stretch and mold very fast although a mis-sized shoe won't feel right ever.

I got a full size and a half size on the way to compare

 

[45bur]

I have owned a few pair of OSB, but the last pair I purchased was 2014 or so. I understand that they have switched suppliers for their mocs - someone said Rancourt makes the shoes now? In any case, has the sizing on the mocs changed since they switched suppliers in 2017 or so?

 

[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 got my 9 and 8.5 Beefroll loafers in. 9.5 as well although I could tell that was too big immediately.

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.

The full size down for me (8.5) is quite snug in the left foot, my bigger one, and snug on the right.

9 is snug on the left and a bit roomy on the right.

Only a few weeks. It happened pretty quickly.

Hmm good to hear

Here are some videos of me comparing the two OSB Beefroll sizes.





I'm at an impass 😅 I KNOW unlined CXL will absolutely stretch. I also know my little toes on the left foot in the 8.5 feel cramped. Not painful just pushed together.

Someone make a decision for me 🤣

 

[SurStyles]

Penny Moc 4 Month Review

I came across the Oak Street Bootmakers Penny Moc after searching for a high quality loafer that could easily transition between casual and business casual clothing. I live in a hot, tropical climate and work in an in-person office on the informal end of business casual. Many people wear jeans and even sneakers to work—I wanted to look more polished without being overly formal/out of place. I also walk back and forth from my home to the office and knew that the shoes would need to be comfortable in action. On weekends I wanted to be able to wear the same loafers with shorts—to slide into them sockless to take the dog for a walk, or run after my daughter at the park. This seemed like a tall list of things to find in a single pair of loafers… but the Penny Moc turned out to be exactly what I was looking for.

I have now had these shoes in brown Chromexcel for over 4 months. For work days or a night out, they look great with chinos or nice jeans and a button-down shirt. On the weekend they look amazing with shorts and a t-shirt. This summer I did an extended trip with the Penny Mocs as one of just two pairs of shoes (the other was a pair of running shoes for exercise). It's hard to imagine a more versatile design. Their main limitation is that you probably wouldn't want to wear these with tailoring. That being said, I wear a sports coat for work meetings 4-5 times a year. I wear a suit maybe once or twice a year—if at all. A smart casual loafer, in my context, actually gets way more mileage than a more formal model.

If there was one element about the design that makes this a great fit for shorts, jeans, or chinos—but not for tailoring—its the flat rubber camp moc sole. Very comfortable for walking or standing for longer periods, good traction. A relaxed look while also presentable.

My one complaint for the Penny Moc is about fit/sizing. OSB recommends that you order a full size down from your Brannock size. I am a 9.5 in Nikes, 9 on Brannock, so I ordered an 8 after reconfirming the recommendation with customer service. When these arrived, I quickly realized that the 8 was painfully small. Toes were totally crunched and it felt so tight that it actually activated sciatic nerve pain in the 30 minutes I wore them around the house. Round 2 I ordered an 8.5. These continued to feel a bit on the small side, but given that Chromexcel stretches, I figured that this had to be it. The reality is that although the shoes have definitely stretched over the last few months, I still feel at times like they squeeze my toes and the ball of my foot a bit. I can now fit a finger behind my heel when sockless—so I don’t think that the length is the issue. I think its more a feature of the last, in that when I walk my foot tends to move towards the narrow front of the shoe and my toes actually push against the leather. This can occasionally get annoying after walking in the heat/as my feet swell. They are still very comfortable probably 95% of the time, and the other 5% it makes me wonder whether a different size or last might have been better (the challenges of purchasing shoes online!).

 

[SurStyles]

My one complaint for the Penny Moc is about fit/sizing. OSB recommends that you order a full size down from your Brannock size. I am a 9.5 in Nikes, 9 on Brannock, so I ordered an 8 after reconfirming the recommendation with customer service. When these arrived, I quickly realized that the 8 was painfully small. Toes were totally crunched and it felt so tight that it actually activated sciatic nerve pain in the 30 minutes I wore them around the house. Round 2 I ordered an 8.5. These continued to feel a bit on the small side, but given that Chromexcel stretches, I figured that this had to be it. The reality is that although the shoes have definitely stretched over the last few months, I still feel at times like they squeeze my toes and the ball of my foot a bit. I can now fit a finger behind my heel when sockless—so I don’t think that the length is the issue. I think its more a feature of the last, in that when I walk my foot tends to move towards the narrow front of the shoe and my toes actually push against the leather. This can occasionally get annoying after walking in the heat/as my feet swell. They are still very comfortable probably 95% of the time, and the other 5% it makes me wonder whether a different size or last might have been better (the challenges of purchasing shoes online!).

See this photo of how my toes hit the end/push against the leather. Is this normal for a moc style loafer?

 

[steadystate]

See this photo of how my toes hit the end/push against the leather. Is this normal for a moc style loafer?
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I think so. I went a full size down, and it was snug at first, and then stretched quite a bit. My toes hit the end on the left one, but it's the nature handsewn with its minor variations and whatnot.

The only possible issue I have is lack of cushioning for the heel; this can make them a bit hard on the foot when walking on pavement, but they're awesome for pretty much everything.

Great review!

 

[coolarrow]

Finally joining the OSB club. CXL beefrolls: