Ezra supple penny loafers Men product image (primary)
Side view of a single black leather penny loafer showing moc-toe stitching, a penny strap with a slit, low stacked heel, and a thin contrasting welt stitch along the sole.

Duke + Dexter

Ezra Supple Penny Loafers Men

CA$500.00CAD
In Stock

The Ezra Supple Penny Loafers are men's slip-on penny loafers with a genuine leather upper and lining, apron/moc toe, padded leather-covered footbed, and non-skid embossed outer sole. They are designed in Canada and made in Portugal, and include a signature storage bag. The black leather style has a penny strap with a center cutout, moc-toe stitching, a low stacked heel, and printed insoles.

Material
Genuine leather upper and lining
Gender
male
Style
classic, smart-casual
Category
Apparel & Accessories > Shoes

Color

Specifications

Classic men's penny loafers crafted with genuine leather and a padded leather-covered footbed.

Genuine leather upper and lining, apron/moc toe, padded footbed with leather top cover, non-skid embossed outer sole, signature storage bag included, made in Portugal.

Material
Genuine leather upper and lining
Style
classic, smart-casual
Occasion
business-casual, everyday
Gender
male
Age Group
adult
Condition
new
Category
Apparel & Accessories > Shoes

Additional Attributes

  • genuine leather upper
  • genuine leather lining
  • apron/moc toe construction
  • penny loafer silhouette
  • padded footbed
  • leather footbed top cover
  • non-skid embossed outer sole
  • signature storage bag included
  • made in Portugal
  • designed in Canada
  • Simons exclusive
  • men's style

Product Insights

Leather upper with rubber sole; lining/sock listed as other materials Measure foot length; choose larger if between sizes Exclusive adds lining, padded footbed and embossed rubber sole vs standard Ezra Natural leather breathes and stays supple Black penny loafer for dress-casual and smart-casual Simons-exclusive design made in Portugal

Verified claims

Exclusivity & origin
Simons-exclusive design made in Portugal
Materials
Leather upper with rubber sole; lining/sock listed as other materials
Lining
Lined interior distinguishes it from standard unlined Ezra
Footbed
Padded footbed with leather top cover
Sole
Non-skid embossed rubber sole
Toe construction
Apron/moc toe with raised stitching
Penny strap
Penny strap with central cutout
Heel
Low stacked heel with embossed heel logo
Insole design
Patterned insole with tattoo-style artwork and branding
Included accessory
Signature storage bag included
Sizing range
EU 41–45 in full sizes only
Sizing advice
Measure foot length; choose larger if between sizes
Stock
All five sizes currently in stock
Colorway
Only Black available
Price consistency
Flat 500 CAD across all sizes
Leather hand
Natural leather breathes and stays supple
Leather authenticity
Assess leather by wrinkle, smell and touch
Seam quality
Inspect apron seam corners for puckering
Styling
Black penny loafer for dress-casual and smart-casual
Comparison
Exclusive adds lining, padded footbed and embossed rubber sole vs standard Ezra
Origin
Made in Portugal

Product record

Title
Ezra Supple Penny Loafers Men
Brand
Duke + Dexter
Price
500 CAD
Availability
In stock

Buying Guide

1 comparison · 12 sources

Product comparison

Compared within this brand.

Why and when to choose each product
This product

Ezra Supple Penny Loafers Men

Duke + Dexter

simons.ca

Same brand

Wilde Snake Penny Loafers Men

Duke + Dexter

simons.ca

Same brand

Van Gogh Skeleton Wilde Penny Loafers Men

Duke + Dexter

simons.ca

Ezra Supple Penny Loafers Men: Choose this if you want a classic black leather penny loafer with a relaxed, unlined feel: the hide is brushed and tumbled for softness, the aprons are pleated, and the brand says the removed lining and pleating deliver added comfort and flexibility. It's a slip-on with a rounded almond toe, penny strap with cutout, raised moc-toe stitching, padded footbed with a leather top cover, and a non-skid 100% rubber sole the brand describes as no less durable than its usual TPU. Made in Portugal, it's a Simons exclusive designed in Canada — though note the composition listing puts the lining and sock as other materials rather than leather, so it suits shoppers fine with an unlined, softer build.[1,2,3,4]Wilde Snake Penny Loafers Men: Choose this if you want a statement penny loafer with personality: an Italian leather upper in a glossy brown-and-tan snakeskin-look print, a contrasting cream vamp with a printed coiled snake motif, and a matching snake-print penny strap. It is a low-heeled loafer with an apron/moc toe, padded leather-covered footbed, genuine leather lining, and an anti-slip TPU outsole, and it is designed in London and handcrafted in a family-run Sheffield workshop, with a signature dust bag included. One wearer reported the fit feels like a glove, worn with socks or hidden socks, though that is a single person's experience, and the outer sole is listed only as other materials.[5,6,7,8,9,10]Van Gogh Skeleton Wilde Penny Loafers Men: Choose this if you want a statement penny loafer with a painted skull motif on the vamp, since this pair pairs an Italian leather upper and leather lining with a padded leather-covered footbed, a TPU anti-slip outsole, UK craftsmanship, and an included dust bag. A wearer reported they fit like a glove with socks or hidden socks, though his expectation that they would also be comfortable without socks was only a hunch. They come in European sizes 41 through 45, so confirm your size falls in that range.[10,11,12]

Image Analysis

3 images
Ezra supple penny loafers Men product image (primary)
01

Product

Side view of a single black leather penny loafer showing moc-toe stitching, a penny strap with a slit, low stacked heel, and a thin contrasting welt stitch along the sole.

  • Overall silhouetteSingle loafer shown in profile with a low heel, rounded toe, and a low-cut collar; shoe rests flat on its sole in a classic penny-loafer shape.
    1 regionx 0.03 · y 0.57 · w 0.94 · h 0.27 (high)
  • Upper materialSmooth pebbled/grain black leather upper with visible natural creasing and a soft sheen.
    1 regionx 0.08 · y 0.57 · w 0.70 · h 0.25 (high)
  • Moc-toe stitchingRaised moc-toe seam running around the front of the shoe, formed by visible hand-style stitches along the toe apron.
    1 regionx 0.74 · y 0.62 · w 0.22 · h 0.18 (high)
  • Penny strapHorizontal strap across the vamp with a central slit typical of penny-loafer styling; strap is made from the same black pebbled leather.
    1 regionx 0.44 · y 0.55 · w 0.38 · h 0.25 (high)
  • Heel constructionLow stacked heel with a slightly protruding rubber or leather heel cap and a flat heel face, finished in black.
    1 regionx 0.03 · y 0.68 · w 0.13 · h 0.12 (high)
  • Welt and sole edgeThin welt visible between upper and sole with a contrasting light stitch line running around the perimeter; sole is low-profile and black.
    1 regionx 0.06 · y 0.79 · w 0.88 · h 0.05 (high)
  • Collar and interior rimInner collar rim shows a smooth leather trim with a slight gloss different from the pebbled outer upper.
    1 regionx 0.10 · y 0.56 · w 0.40 · h 0.12 (medium)

Other

Studio shot on a light gray seamless background with even diffuse lighting and a soft shadow beneath the shoe; shoe is centered horizontally and cropped with ample top margin.

  • Background and stagingNeutral light gray seamless background with no props or packaging visible.
  • Lighting and shadowEven diffuse studio lighting producing soft highlights on the leather and a faint soft-edged shadow directly under the sole.
  • FramingShoe centered horizontally near the lower third of the image with generous empty space above.
  • Image qualityHigh-resolution, well-focused image with clear fine-grain leather texture visible.

Colors

black· upperlight gray· welt stitchblack· heel and sole
Ezra supple penny loafers Men product image 2
02

Product

Pair of black leather penny loafers shown from the rear three-quarter angle; visible features include rounded low heels, welt stitching, embossed small logo on each heel counter, and gold interior text on the heel liners.

  • Rear heel countersBoth shoes show curved rear heel counters made from pebbled black leather with a horizontal seam near the top edge and a vertical seam toward the outer edge.
    2 regionsx 0.05 · y 0.48 · w 0.42 · h 0.37 (high); x 0.49 · y 0.46 · w 0.44 · h 0.39 (high)
  • Embossed heel logoSmall embossed cross-like logo stamped into the leather on the outer side of each heel counter.
    2 regionsx 0.25 · y 0.61 · w 0.06 · h 0.11 (medium); x 0.85 · y 0.60 · w 0.05 · h 0.10 (medium)
  • Low stacked heelLow stacked leather-look heel with a thin welt and a slightly textured outer face, finished in a dark tone matching the sole.
    2 regionsx 0.06 · y 0.72 · w 0.40 · h 0.22 (high); x 0.52 · y 0.71 · w 0.42 · h 0.23 (high)
  • Penny strap and throat (partial)Top edges of the vamp and penny strap are visible above the heel with smooth leather trim; only the rear portion of the strap and throat area is visible.Partial
    2 regionsx 0.12 · y 0.39 · w 0.30 · h 0.20 (medium); x 0.52 · y 0.34 · w 0.30 · h 0.22 (medium)
  • Interior gold text“Gold printed text visible on the heel liners of both shoes.”
    2 regionsx 0.19 · y 0.29 · w 0.14 · h 0.12 (medium); x 0.57 · y 0.28 · w 0.13 · h 0.12 (medium)
  • Visible leather texturePebbled grain texture visible across the shoe uppers with smooth trim along the topline.
    1 regionx 0.05 · y 0.45 · w 0.88 · h 0.45 (high)

Other

Studio-style product shot on a light neutral background showing the rear three-quarter view of the pair; soft shadow beneath shoes and even diffuse lighting.

  • Shot compositionRear three-quarter close-up of a left and right shoe placed side by side with the heels in the foreground and toes pointing away from the camera.
  • Background and surfaceUniform light gray background and surface with subtle soft shadows under the shoes.
  • Lighting qualityDiffuse even lighting with mild specular highlights on smooth leather trim and minimal harsh shadows.
  • Left interior text transcription“Made Different”
    1 regionx 0.18 · y 0.30 · w 0.12 · h 0.10 (medium)
  • Right interior text transcription“Made Different”
    1 regionx 0.57 · y 0.29 · w 0.12 · h 0.10 (medium)

Colors

black· upper leather#0E0D0Dvery dark brown· sole and stacked heel#2D2B2Dmetallic gold· interior heel text
Ezra supple penny loafers Men product image 3
03

Product

Top-down view of a pair of black leather penny loafers showing moccasin-style toe stitching, penny strap with classic cutout, and patterned light-colored insoles with printed artwork and small text elements.

  • Overall silhouettePair of slip-on loafers shown from above with rounded almond toes, low-profile heel, and symmetrical left/right placement.
    2 regionsx 0.06 · y 0.03 · w 0.43 · h 0.94 (high); x 0.51 · y 0.03 · w 0.43 · h 0.94 (high)
  • Upper material and textureSmooth grained black leather upper with visible natural creasing and soft sheen across vamp and quarters.
    2 regionsx 0.06 · y 0.03 · w 0.43 · h 0.46 (high); x 0.51 · y 0.03 · w 0.43 · h 0.46 (high)
  • Moc toe stitchingRaised moccasin-style stitched seam running around the toe perimeter, visible as a stitched ridge following the shoe contour.
    2 regionsx 0.06 · y 0.03 · w 0.43 · h 0.22 (high); x 0.51 · y 0.03 · w 0.43 · h 0.22 (high)
  • Penny strap detailHorizontal penny strap across the vamp of each shoe with a central crescent-shaped cutout and visible stitching along strap edges.
    2 regionsx 0.12 · y 0.28 · w 0.36 · h 0.16 (high); x 0.58 · y 0.28 · w 0.36 · h 0.16 (high)
  • Insole printed artworkLight-colored insoles with multiple black tattoo-style illustrations including a snake, lips, cherries, a dagger-like cluster, and other motifs repeated across both insoles.
    2 regionsx 0.12 · y 0.44 · w 0.26 · h 0.36 (high); x 0.62 · y 0.44 · w 0.26 · h 0.36 (high)
  • Insole text - left“GoodNight”
    1 regionx 0.14 · y 0.40 · w 0.18 · h 0.10 (high)
  • Insole text - brand vertical (partial)“DUKE+DEXTER”Partial
    1 regionx 0.48 · y 0.58 · w 0.08 · h 0.30 (medium)

Other

Studio top-down product shot on a light gray background with soft even lighting and minimal shadows; both shoes fully within frame and centered.

  • Shot compositionTop-down centered composition showing both shoes side by side with small soft shadowing beneath edges.
  • Background and lightingUniform light gray background with diffuse lighting that produces soft highlights on leather surfaces and minimal harsh shadows.
  • Image qualityHigh-resolution image with clear focus across the shoes and visible fine texture on leather and printed insole artwork.

Colors

black· upper leathercream off-white· insole backgroundblack print· insole artwork

Brand PDP Lookup

Brand
Duke + Dexter

Ezra Tan Suede Pleated Ruched Loafer - Women's

Variants

5 SKUs
All variants of Ezra Supple Penny Loafers Men
SKUTitlePriceAvail
4731220Ezra Supple Penny Loafers Men - Black - 41CA$500.00Yes
4680474Ezra Supple Penny Loafers Men - Black - 42CA$500.00Yes
4680475Ezra Supple Penny Loafers Men - Black - 43CA$500.00Yes
4680476Ezra Supple Penny Loafers Men - Black - 44CA$500.00Yes
4680477Ezra Supple Penny Loafers Men - Black - 45CA$500.00Yes

Documents & Data

Provenance

Merchant Link
https://www.simons.ca/en/men-footwear/dress/ezra-supple-penny-loafers-men--22444-26301
Updated