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Main content
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TO BOOT NEW YORK Merrill Penny Loafer, Main, color, Black
TO BOOT NEW YORK Merrill Penny Loafer, Alternate, color, Black
TO BOOT NEW YORK Merrill Penny Loafer, Alternate, color, Black
TO BOOT NEW YORK Merrill Penny Loafer, Alternate, color, Black
TO BOOT NEW YORK Merrill Penny Loafer, Alternate, color, Black
TO BOOT NEW YORK Merrill Penny Loafer, Alternate, color, Black

Merrill Penny Loafer (Men)

TO BOOT NEW YORK

Men
$189.97 – $199.97Current Price $189.97 to $199.97
(Up to 55% off)Up to 55% off.
$425.00Comparable value $425.00
Color: Black
Fit:Runs large; order 1/2 size down.
Size
M
 

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Details & care

A cushioned, arch-supporting footbed adds modern comfort to a timeless penny loafer shaped from smooth Italian leather.

  • Cushioned footbed with arch support
  • Leather upper and lining/rubber sole
  • Made in Italy
  • Item #10519206

Size info

  • Runs large; order 1/2 size down.

Shipping & returns

This item qualifies for free shipping on most orders over $89. Shipping is $9.95 on most orders under $89. Exclusions apply for orders to Alaska, Hawaii and Puerto Rico. Learn more about our shipping & returns policies. 

This item is returnable within 40 days by mail or to any Nordstrom Rack or Nordstrom store.

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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

(10)
3.8 out of 5
Write a Review
Fit: Runs slightly small
Small
True to size
Large
Width: Runs slightly narrow
Narrow
True to width
Wide

Customer photos

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5 stars
50%
4 stars
0%
3 stars
30%
2 stars
20%
1 star
0%
Sort by Most Helpful
Size
Color
Width
AlexanderNY
Verified purchase
Aug 23, 2025
Nice but very tight
Very tight and narrow. One shoe was narrower than the other. I had to return item.
Fit: True to size
Small
True to size
Large
Width: Narrow
Narrow
True to width
Wide
Size purchased: 11.5M
Usual size: 11.5
Color: CAMOSCIO EBANO
1found this helpful
DealSleds
May 2, 2025
runs half size small - maybe
Description says runs big and order half size down. Ordered half size down. Shoes too small and slightly different sizes. Order my true size. One shoe fits the other one is too small. I have two pairs of shoes and all four shoes are different size and fit.
Fit: True to size
Small
True to size
Large
Width: True to width
Narrow
True to width
Wide
Width purchased: M
1found this helpful
GH in CA
Verified purchase
Nov 8, 2025
Much Narrower Than Expected
I've bought several pair of To Boot shoes and they are by far my favorite brand. I ordered these (online) in the size I usually wear (even though the recommendations online were to order a 1/2 size smaller). I got them and the length to the toes was fine, but these were much more narrower than the other To Boot shoes I've bought in the past. I had to return. They looked really nice.
Fit: Small
Small
True to size
Large
Width: Narrow
Narrow
True to width
Wide
Size purchased: 11-1/2
Width purchased: M
Was this helpful?
P.Vei
Verified purchase
Sept 8, 2025
Brown Loafers
Great job. They met all my expectations
Was this helpful?
Anonymous
Verified purchase
Oct 31, 2025
Was this helpful?
ABarry
Verified purchase
Aug 24, 2025
Was this helpful?

6 ratings-only reviews

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    $179.97Current Price $179.97
    (54% off)54% off.
    $399.00Comparable value $399.00
    (2)
  • Mezlan Penny Loafer
    Mezlan
    $199.97Current Price $199.97
    (42% off)42% off.
    $350.00Comparable value $350.00
  • TO BOOT NEW YORK Nova Penny Loafer
    TO BOOT NEW YORK
    $113.98Current Price $113.98
    (74% off)74% off.
    $450.00Comparable value $450.00
    (22)
  • VELLAPAIS Largo Penny Loafer
    VELLAPAIS
    $59.97Current Price $59.97
    (79% off)79% off.
    $289.00Comparable value $289.00
    (1)
  • TO BOOT NEW YORK Memphis Penny Loafer
    TO BOOT NEW YORK
    $179.97Current Price $179.97
    (52% off)52% off.
    $375.00Comparable value $375.00
    (1)
  • VELLAPAIS Decalle Penny Loafer
    VELLAPAIS
    $59.97Current Price $59.97
    (80% off)80% off.
    $309.00Comparable value $309.00
    (3)
  • BOSS Colby Penny Loafer
    Popular
    BOSS
    $119.97Current Price $119.97
    (Up to 33% off)Up to 33% off.
    $165.00 – $180.00Comparable value $165.00 to $180.00
    (5)
  • M BY BRUNO MAGLI Adrian Cap Toe Oxford
    M BY BRUNO MAGLI
    $179.97Current Price $179.97
    (54% off)54% off.
    $395.00Comparable value $395.00
  • TO BOOT NEW YORK Lynwood Loafer
    New Markdown
    TO BOOT NEW YORK
    $95.98 – $159.97Current Price $95.98 to $159.97
    (Up to 74% off select items)Up to 74% off select items.
    $375.00Comparable value $375.00
  • Magnanni Talaz Horsebit Loafer
    New Markdown
    Magnanni
    $142.98 – $229.97Current Price $142.98 to $229.97
    (Up to 64% off select items)Up to 64% off select items.
    $399.00Comparable value $399.00
    (3)
  • BOSS Devin Slip-On Loafer
    BOSS
    $119.97Current Price $119.97
    (39% off)39% off.
    $199.00Comparable value $199.00
    (3)
  • Magnanni Talaz Side Bit Leather Loafer
    Magnanni
    $229.97Current Price $229.97
    (48% off)48% off.
    $445.00Comparable value $445.00
    (5)
  • VELLAPAIS Lenore Tassel Loafer
    VELLAPAIS
    $59.97Current Price $59.97
    (79% off)79% off.
    $289.00Comparable value $289.00
  • MADE IN ITALY Italian Suede Leather Belt
    Popular
    MADE IN ITALY
    $39.97Current Price $39.97
    (42% off)42% off.
    $69.50Comparable value $69.50
    (17)
  • Allen Edmonds Randolph Bit Loafer
    New Markdown
    Allen Edmonds
    $107.98 – $199.97Current Price $107.98 to $199.97
    (Up to 76% off select items)Up to 76% off select items.
    $450.00Comparable value $450.00
    (113)
  • Magnanni Eddison Bit Loafer
    Magnanni
    $219.97Current Price $219.97
    (49% off)49% off.
    $435.00Comparable value $435.00
    (1)
See More
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Merrill Penny Loafer (Men)
TO BOOT NEW YORK
$189.97 – $199.97Current Price $189.97 to $199.97