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Chamberlain Penny Loaferoak
$150
$124

With a slim leather sole, the Chamberlain Penny is our modern version of the timeless, classic penny loafer. Featuring hand-cut, breathable leather and a cushioned insole, the Chamberlain will soon form to the shape of your foot. Whether your domain is mainly in coffee shops or corporate offices, we guarantee that in the Chamberlain you're sure to stand out in the best way possible.

Shop all Essentials

Nubuck leather upper
Full-length, soft leather insole with built-in arch support 
Cushioned, microporous interior fully lined with soft leather for increased comfort 
Classy yet durable nubuck leather outsole 
1-inch stacked leather heel with slip-free rubber heel cap
Handmade in an ethical factory we own and operate in Peru

Fits true to size. They may be snug in the toe and/or heel at first, but they will break in and comfortably stretch after the first few wears. If the heel slips, we recommend adding in a heel snug for a more secure fit. 

Select Size:

Sizing Guide

Color Options:

brandy   oak   brandy  

FIT
With a slim leather sole, the Chamberlain Penny is our modern version of the timeless, classic penny loafer. Featuring hand-cut, breathable leather and a cushioned insole, the Chamberlain will soon form to the shape of your foot. Whether your domain is mainly in coffee shops or corporate offices, we guarantee that in the Chamberlain you're sure to stand out in the best way possible.

Shop all Essentials

Nubuck leather upper
Full-length, soft leather insole with built-in arch support 
Cushioned, microporous interior fully lined with soft leather for increased comfort 
Classy yet durable nubuck leather outsole 
1-inch stacked leather heel with slip-free rubber heel cap
Handmade in an ethical factory we own and operate in Peru

Fits true to size. They may be snug in the toe and/or heel at first, but they will break in and comfortably stretch after the first few wears. If the heel slips, we recommend adding in a heel snug for a more secure fit. 

Based on your feedback we have made several recent improvements to the Chamberlain Penny Loafer, including a now true-to-size fit! All reviews prior to April 2018 do not reflect this update.
Chamberlain Penny Loafer Oak
$124.00
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Sale ends Monday, May 25th at 11:59 pm PT. Use code LETSBEREAL at checkout. Offer cannot be combined or stacked with other discount codes and does not apply to previous orders. Code LETSBEREAL takes an extra 15% off existing markdowns and all full-price products on our sale page only. Due to COVID-19, it may take 3-5 days to ship your order. Thank you for your patience during this time.