Try At Home

Try At Home For 7 Days

Take 7 days after delivery to decide what you’d like to keep.

Pay Later

We’ll place a hold on your card for the full order amount for the duration of your trial. You’ll be charged for the items you decide to keep.

Easy Returns

Don’t love it? Follow our easy return instructions.
All items must be in resellable condition.

Coupon codes and gift cards are not eligible on Try At Home orders.
Powered by TryNow
CLOSE
Your cart

HOLIDAY DEAL

Chamberlain Penny Loafer
$160
$128

Rated 4.1 out of 5
77 Reviews

This item is exchange for store credit only. It cannot be returned for a refund.

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

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:

black

brandy  black  oak 

FIT

This item is exchange for store credit only. It cannot be returned for a refund.

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

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. 

Write a Review
average rating 4.1 out of 5
Based on 77 reviews
  • 5 Stars
    48 Reviews
  • 4 Stars
    7 Reviews
  • 3 Stars
    7 Reviews
  • 2 Stars
    8 Reviews
  • 1 Star
    7 Reviews
71% of reviewers would recommend this product to a friend
77 Reviews
Reviewed by Teague B., from United States
Verified Buyer
Chamberlain Penny Loafer Oak
Reviewing
Chamberlain Penny Loafer Oak
I recommend this product
Rated 5 out of 5
Review posted

Perfect!

These shoes are fantastic. They look and feel great. I've worn them twice so far and get TONS of complements!

Loading...
Was this helpful?
Reviewed by Qamar R., from United States
Verified Buyer
Chamberlain Penny Loafer Oak
Reviewing
Chamberlain Penny Loafer Oak
I recommend this product
Rated 5 out of 5
Review posted

Great quality

Great quality

Loading...
Was this helpful?
Reviewed by Alhareth I., from Saudi Arabia
Verified Buyer
Chamberlain Penny Loafer Black
Reviewing
Chamberlain Penny Loafer Black
I recommend this product
Rated 5 out of 5
Review posted

Awesome

Awesome

Loading...
Was this helpful?
Reviewed by James I., from United States
Verified Buyer
Chamberlain Penny Loafer Brandy
Reviewing
Chamberlain Penny Loafer Brandy
I recommend this product
Rated 5 out of 5
Review posted

Great quality

Very comfortable shoe with a great fit and excellent quality!

Loading...
Was this helpful?
Reviewed by Gaylon G., from United States
Verified Buyer
Chamberlain Penny Loafer Black
Reviewing
Chamberlain Penny Loafer Black
I recommend this product
Rated 5 out of 5
Review posted

Perfectly scaled for today's modern

Perfectly scaled for today's modern wardrobe.

Loading...
Was this helpful?
Chamberlain Penny Loafer Black
$128.00
SELECT SIZE
×

Free Shipping on Orders Over $250 within the contiguous 48 United States before taxes and after discounts are applied.  Orders eligible for free shipping will be delivered via FedEx SmartPost within the CONUS/48 states. Offer does not apply to previous orders.

×

Discount eligible sitewide while supplies last. Use code EXTRA25 at checkout. Cannot be combined or stacked with other discount codes. Offer does not apply to previous orders or gift cards. Offer valid through 11/28/2020 at 11:59PM PST.