Simons
Leather Gathered-Toe Penny Loafers Men
CA$225.00CAD
In Stock
Men's slip-on penny loafers with a genuine leather upper, gathered apron/moc toe stitching, and a horizontal penny strap. They feature a padded footbed with a leather top cover, a non-skid embossed outer sole, and a low stacked heel, and include signature storage bags. Designed in Canada as a Simons exclusive, these loafers are intended for casual and smart-casual wear.
- Material
- Genuine leather upper
- Gender
- male
- Category
- Apparel & Accessories > Shoes
Color
Specifications
Men's gathered-toe penny loafers in genuine leather with a padded leather-covered footbed and non-skid sole, designed in Canada as a Simons exclusive.
Genuine leather upper, apron/moc toe, padded footbed with leather top cover, non-skid embossed outer sole, signature storage bags included.
- Material
- Genuine leather upper
- Gender
- male
- Age Group
- adult
- Condition
- new
- Category
- Apparel & Accessories > Shoes
Additional Attributes
- genuine leather upper
- apron/moc toe
- gathered-toe penny loafer construction
- padded footbed
- leather top cover on footbed
- non-skid embossed outer sole
- signature storage bags included
- Simons exclusive
- designed in Canada
- men's slip-on penny loafer silhouette
Product Insights
Leather Gathered-Toe Penny Loafers Men Leather upper, leather lining and sock, other-material outer sole US 8–13 with half sizes through 11.5 Padded footbed, leather-covered, fixed Use shoe trees, condition leather, wipe sole 225 CAD with leather upper, lining, footbed, bags
Verified claims
- design
- Simons-exclusive design made in Canada
- materials
- Leather upper, leather lining and sock, other-material outer sole
- color
- Black only
- sizing
- US 8–13 with half sizes through 11.5
- width
- Single standard width; no wide option
- sizing
- Measure foot length; choose larger if between sizes
- fit
- Smallest size is US 8, so 7–7.5 wearers must size up
- fit
- No half size above 11.5; 12.5 has no exact match
- fit
- Snug out of the box, molds over first wears
- break-in
- Allow 3–4 weeks and wear gradually
- comfort
- Padded footbed, leather-covered, fixed
- fit
- Do not size down to fix heel slip if forefoot hurts
- fit
- Try on with intended socks and walk indoors
- construction
- Gathered apron/moc toe with penny strap
- heel
- Low stacked-look heel and thin sole profile
- care
- Use shoe trees, condition leather, wipe sole
- storage
- Store in included dust bags, cool and dry
- durability
- Leather can age well with care; sole is replaceable point
- styling
- Polished black loafer for dress and smart casual
- value
- 225 CAD with leather upper, lining, footbed, bags
- branding
- Simons branding printed on insole
Product record
- Title
- Leather Gathered-Toe Penny Loafers Men
- Brand
- Simons
- Price
- 225 CAD
- Availability
- In stock
Buying Guide
1 comparison · 5 sourcesProduct comparison
Compared within this brand.
| Leather Gathered-Toe Penny Loafers Men: Choose this if you want a classic black penny loafer with a genuine leather upper and lining, a padded leather-covered footbed, and a gathered moc toe with a penny strap across the vamp. It is a Simons exclusive designed in Canada, with an embossed non-skid outer sole, offered in Black in sizes 8 through 13, and includes signature storage bags. Note that the outer sole is listed as other material rather than leather, so it suits shoppers prioritizing leather on the upper and interior only.[1,2] | Smooth Leather Penny Loafers Men: Choose this if you want a Simons-exclusive penny loafer designed in Canada and made in Spain, with a polished black leather upper, leather lining and padded leather-covered footbed, moc-toe apron with penny strap, and an embossed non-skid rubber sole — a look that one reviews analysis found suits professional settings thanks to its subtle leather and attractive color. Be aware that the same analysis reports inconsistent sizing (the shoe runs large, and EU 41 does not correspond to US 8), very hard material that may cause a painful break-in, and a twisted-toe defect on the right shoe reportedly found on every pair in one store, making it a gamble unless tried on in person.[3] | Santiago Suede Penny Loafers Men: Choose this if you want a classic suede penny loafer with traditional details, including a moc-toe apron, penny strap with cutout, low stacked heel, and easy slip-on entry. It features a genuine suede upper, padded footbed with a leather top cover, and a leather outsole with a rubberized forefoot and heel that the brand says is for better grip, and it comes in European sizes 40 through 45 as a Simons exclusive designed in Canada and made in Portugal. Note that the lining and sock are synthetic rather than leather, which may matter if you prefer fully natural materials.[4,5] |
Image Analysis
3 images- 01
Product
Side view of a single black leather penny loafer showing gathered moc-toe, vamp strap with penny slot, low stacked heel, and smooth polished upper leather.
- Overall silhouetteSingle left-facing shoe shown in profile (outer side visible) with a low heel and a gently rounded toe.
1 region
x 0.03 · y 0.48 · w 0.94 · h 0.32 (high) - Upper material and finishSmooth polished black leather upper with a subtle sheen and even surface, showing reflected highlights along the vamp and quarter.
1 region
x 0.05 · y 0.50 · w 0.70 · h 0.22 (high) - Gathered toe / moc stitchingGathered pleated leather detail around the toe with visible moc-style stitching along the seam just above the sole.
1 region
x 0.66 · y 0.52 · w 0.30 · h 0.22 (high) - Vamp strap (penny slot)Horizontal vamp strap across the mid-vamp with a narrow slot (penny-style) and a small stitched detail where the strap meets the vamp.
1 region
x 0.45 · y 0.46 · w 0.28 · h 0.16 (high) - Heel constructionLow stacked heel with layered appearance and a slightly textured side; heel top transitions to the quarter with a stitched seam.
1 region
x 0.03 · y 0.66 · w 0.20 · h 0.14 (high) - Outsole and midsoleBlack outsole with a thin slightly protruding edge visible along the toe and forefoot, creating a defined sole line and a shallow sole profile.
1 region
x 0.06 · y 0.70 · w 0.88 · h 0.12 (high)
Other
Studio product shot on a plain light gray background with soft directional lighting from above, centered composition, and a soft shadow under the shoe.
- Background and stagingEven light gray seamless background with no props or packaging visible.
- Lighting and shadowSoft studio lighting producing subtle highlights on the leather and a soft cast shadow directly beneath and slightly to the right of the shoe.
1 region
x 0.10 · y 0.77 · w 0.80 · h 0.10 (medium) - Framing and cropShoe is centered horizontally and positioned in the lower half of the frame, leaving a large empty area above.
Colors
gloss black· upper leathermatte black· sole and heel- Overall silhouetteSingle left-facing shoe shown in profile (outer side visible) with a low heel and a gently rounded toe.
- 02
Product
Rear-quarter studio view of two black leather penny loafers showing the heel, back seam, stitching, and stacked-look sole.
- Rear heel profileVisible rear-quarter of a black leather loafer showing a rounded heel counter with a vertical back seam and a slightly tapered top edge.
1 region
x 0.40 · y 0.32 · w 0.40 · h 0.47 (high) - Upper material and finishSmooth black leather upper with a low-sheen polished finish and fine visible grain under studio lighting.
1 region
x 0.38 · y 0.30 · w 0.44 · h 0.40 (high) - Stacked-look sole and heelLayered, stacked-look heel and sole in a dark grey to black tone with visible horizontal lines indicating stacked layers.
2 regions
x 0.38 · y 0.68 · w 0.44 · h 0.20 (high); x 0.00 · y 0.60 · w 0.36 · h 0.20 (medium) - Stitching detailTopline seam and a horizontal stitch running near the top edge of the heel counter, plus a short vertical reinforcement stitch at the base of the back seam.
1 region
x 0.42 · y 0.33 · w 0.28 · h 0.30 (high) - Inner heel code“M258-1822”Partial
1 region
x 0.61 · y 0.19 · w 0.23 · h 0.15 (medium) - Secondary shoe rearPartial view of the second loafer's rear-quarter visible in the left background with matching leather and stitching details.
1 region
x 0.00 · y 0.33 · w 0.38 · h 0.36 (medium)
Other
Studio product shot with neutral light-gray background, soft top lighting, and a soft shadow under shoes; image is tightly cropped around the lower half of the shoes.
- Background and stagingEven light-gray seamless background with no props, creating a high-contrast presentation of the shoes.
- Lighting and shadowSoft directional lighting from above-left producing gentle highlights on the leather and faint shadow beneath the soles.
- Crop and compositionTight crop focusing on the rear and heel area; upper front parts of the shoes are mostly out of frame.
Colors
black· leather upperdark charcoal· stacked heel and sole- Rear heel profileVisible rear-quarter of a black leather loafer showing a rounded heel counter with a vertical back seam and a slightly tapered top edge.
- 03
Product
Top-down view of a pair of black leather penny loafers with gathered apron stitching, smooth vamps and a penny strap featuring a curved cutout. White brand text is printed on each insole.
- Overall shapePair of slip-on loafers shown from above with rounded toes, low collars and flat soles; shoes are positioned parallel with toes at the top of the image.
- Upper material and finishSmooth leather vamp and strap with a subtle sheen consistent with polished leather.
1 region
x 0.12 · y 0.12 · w 0.76 · h 0.56 (high) - Gathered apron stitchingDistinct gathered/ruched stitching runs around the toe apron on both shoes, forming a raised stitched seam that follows the toe contour.
2 regions
x 0.06 · y 0.04 · w 0.43 · h 0.36 (high); x 0.51 · y 0.04 · w 0.43 · h 0.36 (high) - Penny strap and cutoutHorizontal penny strap across the vamp of each shoe with a shallow, curved cutout detail in the center of the strap.
2 regions
x 0.15 · y 0.30 · w 0.30 · h 0.18 (high); x 0.55 · y 0.30 · w 0.30 · h 0.18 (high) - Insole text branding“simons”
2 regions
x 0.17 · y 0.66 · w 0.20 · h 0.20 (high); x 0.59 · y 0.66 · w 0.20 · h 0.20 (high) - Stitch detail along strap and apronVisible single-row topstitching along the edge of the penny strap and along the apron seam.
1 region
x 0.12 · y 0.20 · w 0.76 · h 0.34 (medium) - Sole and heel profileThin, low-profile sole visible around the shoe perimeter with a slightly raised heel area at the rear of each shoe.
1 region
x 0.08 · y 0.76 · w 0.84 · h 0.20 (medium)
Other
Studio-style top-down product photo on a neutral light gray background with even lighting and soft shadows below the shoes.
- Background and stagingPlain light gray background with no props; shoes centered in frame and photographed from above.
- Lighting and shadowEven diffuse studio lighting producing soft highlights on leather and faint soft shadows beneath the shoes toward the bottom of the image.
- Crop and compositionBoth shoes fully visible and symmetrically arranged; small margin of background visible on all sides.
Colors
polished black· upper leatherdark olive black· insolewhite· insole text
Variants
10 SKUs| SKU | Title | Price | Avail |
|---|---|---|---|
| 4745135 | Leather Gathered-Toe Penny Loafers Men - Black - 8 | CA$225.00 | Yes |
| 4745136 | Leather Gathered-Toe Penny Loafers Men - Black - 8.5 | CA$225.00 | Yes |
| 4745137 | Leather Gathered-Toe Penny Loafers Men - Black - 9 | CA$225.00 | Yes |
| 4745138 | Leather Gathered-Toe Penny Loafers Men - Black - 9.5 | CA$225.00 | Yes |
| 4745139 | Leather Gathered-Toe Penny Loafers Men - Black - 10 | CA$225.00 | Yes |
| 4745140 | Leather Gathered-Toe Penny Loafers Men - Black - 10.5 | CA$225.00 | Yes |
| 4745141 | Leather Gathered-Toe Penny Loafers Men - Black - 11 | CA$225.00 | Yes |
| 4745142 | Leather Gathered-Toe Penny Loafers Men - Black - 11.5 | CA$225.00 | Yes |
| 4745143 | Leather Gathered-Toe Penny Loafers Men - Black - 12 | CA$225.00 | Yes |
| 4745144 | Leather Gathered-Toe Penny Loafers Men - Black - 13 | CA$225.00 | Yes |