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Main content
  1. Home
  2. Men
  3. Shoes
  4. Dress Shoes
  5. Loafers
TO BOOT NEW YORK Tesoro Penny Loafer, Main, color, Black
TO BOOT NEW YORK Tesoro Penny Loafer, Alternate, color, Black
Tesoro Penny Loafer, sales video thumbnail
TO BOOT NEW YORK Tesoro Penny Loafer, Alternate, color, Black
TO BOOT NEW YORK Tesoro Penny Loafer, Alternate, color, Black
TO BOOT NEW YORK Tesoro Penny Loafer, Alternate, color, Black

Tesoro Penny Loafer (Men)

TO BOOT NEW YORK

Men
$399.00 – $450.00Current Price $399.00 to $450.00
Color: Black
Size
M
Free returns anytime
Sold by Nordstrom
$60 off your next purchase ends March 8. Plus, earn 10 points per dollar March 4–8.  See Terms & Apply

Details & care

Streamlined design showcases the rich leather of a timeless penny loafer built with cushioned arch support and a flexible sole for superior comfort.

  • Cushioned insole with arch support
  • Leather upper, lining and sole
  • Made in Italy
  • Item #5950643

Size info

  • Our fit experts say if between sizes, order 1/2 size down.
  • M=medium width

Shipping & returns

Free shipping. Free returns. All the time. Purchases made online can also be returned or exchanged at any Nordstrom store, free of charge. Read more about our shipping & returns policies.

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TO BOOT NEW YORK

For more than 25 years, To Boot New York has created modern footwear using time-honored traditions. Crafted in Italy of top-tier materials, each shoe is made entirely by hand, from the cutting and sewing to the final polishing. Known for offering a variety of contemporary styles to fit all facets of a man's lifestyle, the brand has developed a loyal following over the years.

Reviews

(27)
4.1 out of 5
Write a Review
Fit: Runs slightly small
Small
True to size
Large
Width: Runs slightly narrow
Narrow
True to width
Wide

Most helpful positive review

Mar 8, 2020
Worth the wait
Love ToBoot.... have been waiting for a new leather soled loafer and this was worth the wait. As great as the brand is - sometimes their sizes are strange.... loafers are always hard for orthotics as they can pinch in the wrong spots or be too loose. These are fantastic. They look great. They’re light weight and flexible. Super comfortable. And they fit just right......
AS_NJ
5found this helpful

Most helpful critical review

Dec 29, 2023
Mislabeled shoes
I ordered a 10.5, the box said 10.5 but the shoes within were 8.5. Disappointing on Christmas morning and lame that I had to take my time to return them. The cashier said nothing, very disappointing service.
Erica Tdubs
Verified purchase
2found this helpful
5 stars
70%
4 stars
7%
3 stars
0%
2 stars
7%
1 star
15%

Pros:

Cons:

Current reviews don’t mention any.
Sort by Most Helpful
Size
Color
Width
AS_NJ
Mar 8, 2020
Worth the wait
Love ToBoot.... have been waiting for a new leather soled loafer and this was worth the wait. As great as the brand is - sometimes their sizes are strange.... loafers are always hard for orthotics as they can pinch in the wrong spots or be too loose. These are fantastic. They look great. They’re light weight and flexible. Super comfortable. And they fit just right......
Fit: True to size
Small
True to size
Large
Width: True to width
Narrow
True to width
Wide
5found this helpful
Erica Tdubs
Verified purchase
Dec 29, 2023
Mislabeled shoes
I ordered a 10.5, the box said 10.5 but the shoes within were 8.5. Disappointing on Christmas morning and lame that I had to take my time to return them. The cashier said nothing, very disappointing service.
Fit: Small
Small
True to size
Large
Size purchased: 10.5
2found this helpful
QuarkXP
Verified purchase
Apr 3, 2025
Sent Them Back for Various Reasons
First, the box these arrived in was in really tough shape. Nordstrom just wrapped it in their signature plastic bag. One entire section of the box was actually torn and ripped when taken out of the bag. The tissue paper in the box was thrown all about, and just looked tired. I believe the store they were shipped from (Mall of America was on the shipping label) knew this, too, as they had two rubber bands around the box. I overlooked this, however, as I ordered the shoes, not the box. Still... presentation DOES play a part in things when coming from a store such as Nordstrom. Upon opening the box, I was surprised at how the shoes appeared to be "cheap." Not sure why they looked this way to me, but they did. I've had shoes at half the cost of these not give me that impression upon opening the box. They felt good when putting them on, and even with an orthotic inserted, they fit well, so I was pleased with that. HOWEVER, and it's a big HOWEVER... when I started to walk and test them out on a carpeted surface, I could tell the cushioning in these was very poor and my right foot started to ache rather quickly. I do realize with my orthotics that this issue can come into play, especially with my right foot. However, I haven't felt a reaction so quickly with new shoes before as I have with these. I put them back in the box and tried it again a few hours later and the same thing happened. I grabbed a pair of my older dress loafers (the ones I intended to replace with these new ones) and felt fine. I really like the style of these and the color options, too. Believe it or not, it's sometimes hard to find a pair of shoes in a style that suits our tastes and then want colors beyond a standard black or brown. So the color options here are definitely good, but the cushioning--or lack thereof--in these is seemingly really poor. Of note, the brand's own website mentions nothing about cushioning/removable insole, etc. Needless to say, I sent them back.
Fit: True to size
Small
True to size
Large
Width: Runs slightly narrow
Narrow
True to width
Wide
Size purchased: 12M
Usual size: 12
Color: BRANDY ANT
1found this helpful
Hamilton B
May 28, 2022
beautiful loafer
Great shoe, beautiful feel, look, & comfort. Bought it for a wedding and i definitely had the best shoes there!
Fit: True to size
Small
True to size
Large
Width: True to width
Narrow
True to width
Wide
1found this helpful
Joecangolf
Verified purchase
June 25, 2025
Second purchase of same shoes
Great shoes love the fit and look
Was this helpful?
Henry P
Verified purchase
July 27, 2024
Just what I wanted
Well constructed, excellent fit and the right price.
Size purchased: 41
Color: Black
Was this helpful?
Load 3 more reviews

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Tesoro Penny Loafer (Men)
TO BOOT NEW YORK
$399.00 – $450.00Current Price $399.00 to $450.00
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