
Duke + Dexter
Willis Thready Penny Loafers Men
These are men's penny loafers with a brown hairy-texture genuine leather upper and leather lining, intended for casual slip-on wear. They feature an apron/moc toe, penny strap, padded footbed with leather top cover, non-skid embossed outer sole, and stacked dark brown heel. The shoes are made in Portugal, include a signature storage bag, and are a Simons exclusive designed in Canada; the insole is printed with DUKE + DEXTER graphics.
- Material
- Genuine leather upper and lining; leather top cover on padded footbed
- Gender
- male
- Style
- classic, preppy, smart-casual, heritage
- Category
- Apparel & Accessories > Shoes
Color
Specifications
Men's classic penny loafers crafted with a genuine leather upper and lining, padded footbed, and non-skid sole.
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; leather top cover on padded footbed
- Style
- classic, preppy, smart-casual, heritage
- Occasion
- everyday, business-casual, work, weekend
- Gender
- male
- Age Group
- adult
- Condition
- new
- Category
- Apparel & Accessories > Shoes
Additional Attributes
- Simons exclusive design developed in Canada
- Men's penny loafer silhouette
- Slip-on styling
- Genuine leather upper
- Genuine leather lining
- Apron/moc toe construction
- Padded footbed
- Leather top cover on footbed
- Non-skid embossed outer sole
- Signature storage bag included
- Made in Portugal
Product Insights
Mossy Green colourway with a heathered, hairy texture Measure heel to longest toe and choose the larger size if between sizes Suede upper with a coarse, hairy 'thready' pile Brush suede nap and use a suede renovator spray 425 CAD for a made-in-Portugal, leather-lined suede loafer with storage bag
Verified claims
- color
- Mossy Green colourway with a heathered, hairy texture
- sizing
- EU sizes 41-45, men's fit, five variants
- fit_guidance
- Measure heel to longest toe and choose the larger size if between sizes
- size_availability
- Unbroken 41-45 run, all in stock
- price_parity
- Same 425 CAD across all sizes
- size_range_boundaries
- EU 41 and EU 45 are the outer limits
- color_availability
- Mossy Green held across all sizes
- upper_material
- Suede upper with a coarse, hairy 'thready' pile
- lining_footbed
- Leather lining and sock with padded footbed and leather top cover
- moc_toe_construction
- Apron/moc toe with penny strap and raised stitching
- sole
- Non-skid embossed outer sole with thin welt
- heel
- Low squared stacked heel in darker brown
- origin
- Made in Portugal; Simons exclusive designed in Canada
- included_accessory
- Signature storage bag included
- shoe_tree
- Cedar shoe tree recommended to preserve shape and absorb moisture
- care
- Brush suede nap and use a suede renovator spray
- barefoot_wear
- Barefoot or invisible-sock wear is viable but needs moisture care
- styling
- Socks and trouser hem set the formality; keep hem slightly shortened to show the strap
- versatility
- Bridges formal and casual, working with suits and jeans
- insole_detail
- Printed insole graphics with Duke + Dexter branding
- value
- 425 CAD for a made-in-Portugal, leather-lined suede loafer with storage bag
Product record
- Title
- Willis Thready Penny Loafers Men
- Brand
- Duke + Dexter
- Price
- 425 CAD
- Availability
- In stock
Buying Guide
1 comparison · 9 sourcesProduct comparison
Compared within this brand.
| Willis Thready Penny Loafers Men: Choose this if you want a slip-on penny loafer with a distinctive fuzzy, hairlike suede upper in Mossy Green, detailed with a raised moc-toe seam, visible stitching, a penny strap, and a stacked heel. It suits dress-casual wardrobes thanks to a leather lining and sock, a padded footbed with a leather top cover, and an embossed non-skid outer sole, in sizes 41 through 45 with a signature storage bag included. Note that the listing describes the upper inconsistently as both genuine leather and suede, so material-conscious shoppers may want to confirm before ordering.[1,2] | Wilde Snake Penny Loafers Men: Choose this if you want a statement penny loafer: it pairs a high-quality Italian leather upper with a snakeskin look (a digital print, not actual snakeskin), a contrasting cream vamp panel with a printed coiled snake motif, and a matching snake-print penny strap. It offers full leather lining, a padded footbed with a leather top cover, and a TPU outsole with anti-slip grip, and is made in the UK—handcrafted in a family-run workshop in Sheffield, according to The Rake. One wearer reports the Wilde loafers fit like a glove worn with socks or hidden socks, and they come in European sizes 41 to 45.[3,4,5,6,7] | Van Gogh Skeleton Wilde Penny Loafers Men: Choose this if you want a statement dress loafer: a black penny loafer with a painted skull motif on the vamp, made in the UK with an Italian leather upper, genuine leather lining, and a padded leather-covered footbed. It has a TPU outsole with anti-slip grip and includes a signature dust bag, and one wearer reports a glove-like fit with or without socks, though comfort without socks is that wearer's expectation. Sizes run from 41 to 45, so it suits those wanting bold artwork on a classic silhouette.[7,8,9] |
Image Analysis
3 images- 01

Product
Side view of a single brown textured penny loafer showing a hairy-texture upper, moc-toe stitching, a penny strap, and a dark stacked sole and heel.
- Overall silhouetteSingle left-facing loafer shown in full side profile with low vamp, rounded moc-toe, and a short stacked heel.
1 region
x 0.06 · y 0.54 · w 0.88 · h 0.23 (high) - Upper material textureUpper has a coarse, hairy textured surface with many short lighter fibers distributed across a brown base, producing a fuzzy appearance.
1 region
x 0.06 · y 0.54 · w 0.78 · h 0.20 (high) - Moc-toe stitchingRaised moc-toe seam running around the front of the shoe with visible topstitching along the apron.
1 region
x 0.12 · y 0.60 · w 0.68 · h 0.11 (high) - Penny strapA horizontal penny-style strap sits across the vamp with visible stitching and a narrow slot-like cutout.
1 region
x 0.46 · y 0.57 · w 0.26 · h 0.10 (high) - Sole and weltThin dark brown welt and rubberized outsole visible along the lower edge, creating a slight contrast with the upper.
1 region
x 0.06 · y 0.74 · w 0.88 · h 0.08 (high) - Stacked heelLow squared stacked heel in a darker brown tone with a visible seam where it meets the sole.
1 region
x 0.03 · y 0.70 · w 0.18 · h 0.12 (high) - Inner lining visibleA narrow strip of darker interior lining is visible at the shoe opening behind the vamp.
1 region
x 0.36 · y 0.56 · w 0.12 · h 0.05 (medium)
Other
Studio product shot on a light gray seamless background with soft shadow beneath the shoe; shoe centered horizontally and positioned in lower half of frame.
- Background and stagingLight neutral gray seamless background filling the frame, isolating the shoe.
- ShadowSoft diffuse shadow directly beneath the shoe following its outline, indicating overhead studio lighting.
1 region
x 0.06 · y 0.75 · w 0.88 · h 0.05 (medium) - Shot compositionShoe is centered horizontally and placed near the lower third of the image with ample empty space above.
Colors
warm medium brown with beige fibers· upperoff-beige· lighter surface fibers#EDEDEDdark brown· sole and heel#352B2A- Overall silhouetteSingle left-facing loafer shown in full side profile with low vamp, rounded moc-toe, and a short stacked heel.
- 02

Product
Rear three-quarter view of two brown textured penny loafers showing the uppers, heel counters, penny straps and stacked dark brown soles; interior tan lining with partial stamped text is visible.
- Overall silhouettePair of low-profile slip-on loafers shown from the rear three-quarter angle with both heel counters and outer sides visible; toes are toward the image center and heels toward the bottom edge.
1 region
x 0.05 · y 0.45 · w 0.90 · h 0.45 (high) - Upper material textureBrown upper with a coarse, hairy texture composed of short fiber tufts in lighter and darker shades, giving a visibly fuzzy surface.
1 region
x 0.10 · y 0.50 · w 0.60 · h 0.30 (high) - Penny strap and toplineVisible penny strap on the right shoe with the strap edge and topline edged by a thin stitched welt; strap is made from the same textured material as the upper.
1 region
x 0.58 · y 0.42 · w 0.30 · h 0.20 (high) - Heel counter detailHeel counters are rounded and covered with the same hairy textured upper; visible horizontal seam and subtle cross-shaped stitch detail on outer sides of each heel.
2 regions
x 0.06 · y 0.58 · w 0.28 · h 0.20 (high); x 0.62 · y 0.60 · w 0.30 · h 0.22 (high) - Sole and heel construction visibleStacked dark brown flat heels and outsoles with a slightly raised heel block and a thin welt between upper and sole.
2 regions
x 0.05 · y 0.70 · w 0.40 · h 0.18 (high); x 0.55 · y 0.70 · w 0.38 · h 0.22 (high) - Interior lining text partial“Made in”Partial
1 region
x 0.62 · y 0.35 · w 0.18 · h 0.10 (medium)
Other
Studio product shot on a light gray seamless background with soft shadow beneath the shoes; image cropped to focus on the rear portion of the pair.
- Background and stagingUniform light gray seamless background occupying the full frame with a soft shadow beneath the shoes indicating top-front lighting.
- Shot compositionRear three-quarter composition with shoes placed slightly offset from center and photographed close-up so that upper textures and sole profiles are prominent.
Colors
textured warm brown· upper#7B5C43light beige fleck· fiber flecks on upperdark brown· sole and heel#342C2Btan leather· interior lining- Overall silhouettePair of low-profile slip-on loafers shown from the rear three-quarter angle with both heel counters and outer sides visible; toes are toward the image center and heels toward the bottom edge.
- 03

Product
Top-down view of a pair of brown, hairy-texture penny loafers showing the uppers, penny straps, apron stitching, and printed insoles.
- Uppers material and textureBoth shoe uppers are covered in a coarse, furlike pile with visible short hair fibers in brown with lighter pale fiber flecks.
2 regions
x 0.05 · y 0.03 · w 0.43 · h 0.94 (high); x 0.52 · y 0.03 · w 0.43 · h 0.94 (high) - Penny strapEach shoe has a horizontal penny strap across the vamp with a slit detail; the strap is made from the same hairy material and stitched to the vamp.
2 regions
x 0.13 · y 0.28 · w 0.34 · h 0.18 (high); x 0.60 · y 0.28 · w 0.34 · h 0.18 (high) - Apron stitching and toe shapeRounded toe with raised apron seam following the toe outline; stitching is visible and matches the hairy upper, creating a stitched rim around the toe box.
2 regions
x 0.07 · y 0.04 · w 0.40 · h 0.40 (high); x 0.53 · y 0.04 · w 0.40 · h 0.40 (high) - Visible sole rimA thin dark sole rim is visible around the outer edge of both shoes, contrasting with the brown upper.
2 regions
x 0.02 · y 0.02 · w 0.06 · h 0.96 (medium); x 0.92 · y 0.02 · w 0.06 · h 0.96 (medium) - Left insole illustrationsLeft shoe insole shows multiple black printed illustrations including a snake, a chain link motif, and other small graphics; illustrations are printed on a light background.
1 region
x 0.12 · y 0.45 · w 0.30 · h 0.40 (high) - Right insole illustrationsRight shoe insole shows black printed illustrations including a snake, a head/bust drawing, darts, stars, and a scorpion on a light background.
1 region
x 0.57 · y 0.45 · w 0.30 · h 0.40 (high) - Insole brand text“DUKE + DEXTER”
1 region
x 0.66 · y 0.58 · w 0.14 · h 0.28 (high)
Other
Top-down studio shot on a uniform light grey background with even lighting and soft shadow beneath shoes; image is tightly cropped with both shoes centered and fully visible.
- Shot compositionTop-down view with both shoes parallel and heels toward the bottom of the image; shoes centered on a neutral background.
- Background and lightingFlat, light grey background with soft, diffused lighting producing faint shadows beneath the shoes.
- Image qualitySharp focus on shoe texture and insole prints; no visible motion blur or noise.
Colors
warm brown with pale flecks· upper (hairy pile)#83634Clight beige· insole background#CDC1B4dark brown / near black· sole rimpale grey fleck· hair flecks- Uppers material and textureBoth shoe uppers are covered in a coarse, furlike pile with visible short hair fibers in brown with lighter pale fiber flecks.
Variants
5 SKUs| SKU | Title | Price | Avail |
|---|---|---|---|
| 4731222 | Willis Thready Penny Loafers Men - Mossy Green - 41 | CA$425.00 | Yes |
| 4680493 | Willis Thready Penny Loafers Men - Mossy Green - 42 | CA$425.00 | Yes |
| 4680494 | Willis Thready Penny Loafers Men - Mossy Green - 43 | CA$425.00 | Yes |
| 4680495 | Willis Thready Penny Loafers Men - Mossy Green - 44 | CA$425.00 | Yes |
| 4680496 | Willis Thready Penny Loafers Men - Mossy Green - 45 | CA$425.00 | Yes |