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Florsheim
Florsheim Berkley Penny Loafer
−56%
Shoes · ShopSimon

Florsheim Berkley Penny Loafer

Deal score 6.7 · Great deal
$63.90$145.00 ShopSimon's regular price

You save $81.10 at ShopSimon

Deal.ai's agents found this deal on November 5. The store may have changed its price since.

Why it's a great deal

  • Elsewhere right now: DSW $129.99, Florsheim Shoes $145.00, Macy's $145.00, and 2 more (typical $145.00 across 5 stores)
  • Cheaper than all 5 other stores selling it right now
  • ShopSimon lists its regular price at $145.00: 56% off by its own figures
  • Rated 4.3 out of 5 by 1,200 buyers
Visit ShopSimon

Every store we checked

  • ShopSimonNew

    In stock

    $63.90Observed Nov 5, 2026, 6:47 PM
    Visit store
  • Florsheim ShoesNew

    In stock

    $145.00Observed Nov 5, 2026, 6:47 PM
    Visit store
  • Macy'sNew

    In stock

    $145.00Observed Nov 5, 2026, 6:47 PM
    Visit store
  • Zappos.comNew

    In stock

    $145.00Observed Nov 5, 2026, 6:47 PM
    Visit store
  • TheShoeMartNew

    Availability unknown

    $144.95Observed Nov 5, 2026, 6:47 PM
    Visit store
  • eBayNew

    Availability unknownSold by theshoemart

    $144.95Observed Nov 5, 2026, 6:47 PM
    Visit store
  • WalmartNew

    Availability unknownSold by Seller

    $145.00Verified
    Visit store
Price history and every store's price →

Reading ShopSimon’s product page for the details…

About it

A timeless classic, the penny loafer never goes out of style. Featuring genuine handsewn construction, stacked heel, and a genuine leather sole, whether it's with a suit or jeans, the Florsheim Berkley Moc Toe Penny Loafer has a rich look that is sure to get noticed. Leather sourced from a tannery with a Gold or Silver rating for environmental responsibility by the independent auditing group, the Leather Working Group.

Specs

Numeric Size
10
Fit Width
Narrow, Medium, Wide
Gender Size
Men's 10.5, Men's 11, Men's 11.5, Men's 12, Men's 13
Men'S Size
Size 10.5, Size 11, Size 11.5, Size 12, Size 13
Age Group Size
Adult size
Department
Men's
Suitable For Size
Men's Size
Age Group
Adult
Occasion
With a suit or jeans
Running Shoes
No

About the Florsheim Berkley Penny Loafer

The Florsheim Berkley is a classic men's penny loafer with a moc toe, handsewn construction, a stacked heel and a genuine leather sole. It comes in narrow, medium and wide widths, including extra-wide 3E, which is the main reason shoppers pick it over slimmer loafers. The best new price is $63.90 at ShopSimon as of November 5, 2026, with 7 stores selling it new. That is well below the $100–$150 the Berkley usually sells for, so this is a strong price for a leather-soled loafer.

Best forMen who need wide or extra-wide (3E) dress shoesWearing with a suit or with jeansAll-day office and everyday wearShoppers who want a leather sole and handsewn construction
Pros
  • Available in narrow, medium, wide and 3E widths
  • Genuine handsewn construction with a stacked heel
  • Leather sole and Leather Working Group–rated leather
  • Versatile enough for suits and jeans
  • Rated 4.3 out of 5 from 1,200 ratings
Cons

More deals like this

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Leather sole is slick on wet pavement and needs a break-in
  • Burgundy and red colorways are harder to match than black or brown
  • Sizing runs inconsistent between widths, so try before committing
  • Leather sole wears faster than rubber for heavy daily walking
  • What reviewers say

    • 4.3 / 51,200 ratings

    Owners rate the Berkley well, at 4.3 out of 5 from 1,200 ratings, and most praise the leather, the classic look and the wide fits. Complaints center on break-in stiffness and sizing that varies by width.

    What people mention
    • Fit and widthPraisedBuyers say the narrow through 3E widths let men with wide feet get a proper fit.
    • Break-inMixedSeveral owners find the shoes stiff at first but comfortable after a few wears.
    • Leather qualityPraisedReviewers describe the leather as rich-looking and holding up well with polish.
    • SoleMixedThe leather sole is praised for its dressy look but called slippery when new.
    • SizingCriticisedSome buyers say the fit differs between widths and recommend checking size carefully.

    Questions and answers

    Is $63.90 a good price for the Florsheim Berkley?
    Yes. The Berkley usually sells for around $100 to $150, so $63.90 at ShopSimon as of November 5, 2026 is a low price. Seven stores sell it new, so compare sizes and widths before buying.
    Does the Berkley come in wide sizes?
    Yes. It comes in narrow, medium, wide and extra-wide 3E. The 11.5 3E in burgundy is one of the listed options.
    How does the Berkley fit compared with other loafers?
    It fits like a standard loafer, but owners report differences between widths. If you are between sizes, size up in the narrow width and check the 3E if you have wide feet.
    What is the sole made of?
    The Berkley has a genuine leather sole with a stacked heel. It looks dressy but is slick on wet ground until scuffed.
    Can I wear the Berkley with jeans?
    Yes. The moc-toe penny loafer style works with jeans and with a suit, which is why it is listed for both.
    How long does the Berkley take to break in?
    Expect a few wears. The leather and sole soften with use, and owners say it becomes comfortable for all-day wear after that.
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