
Duke + Dexter
Ezra Supple Penny Loafers Men
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 sourcesProduct comparison
Compared within this brand.
| 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- 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 region
x 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 region
x 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 region
x 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 region
x 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 region
x 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 region
x 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 region
x 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- 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.
- 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 regions
x 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 regions
x 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 regions
x 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 regions
x 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 regions
x 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 region
x 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 region
x 0.18 · y 0.30 · w 0.12 · h 0.10 (medium) - Right interior text transcription“Made Different”
1 region
x 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- 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.
- 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 regions
x 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 regions
x 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 regions
x 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 regions
x 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 regions
x 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 region
x 0.14 · y 0.40 · w 0.18 · h 0.10 (high) - Insole text - brand vertical (partial)“DUKE+DEXTER”Partial
1 region
x 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- Overall silhouettePair of slip-on loafers shown from above with rounded almond toes, low-profile heel, and symmetrical left/right placement.
Brand PDP Lookup
- Brand
- Duke + Dexter
Ezra Tan Suede Pleated Ruched Loafer - Women's
Variants
5 SKUs| SKU | Title | Price | Avail |
|---|---|---|---|
| 4731220 | Ezra Supple Penny Loafers Men - Black - 41 | CA$500.00 | Yes |
| 4680474 | Ezra Supple Penny Loafers Men - Black - 42 | CA$500.00 | Yes |
| 4680475 | Ezra Supple Penny Loafers Men - Black - 43 | CA$500.00 | Yes |
| 4680476 | Ezra Supple Penny Loafers Men - Black - 44 | CA$500.00 | Yes |
| 4680477 | Ezra Supple Penny Loafers Men - Black - 45 | CA$500.00 | Yes |