Simons
Smooth Leather Derby Shoes Men
CA$195.00CAD
In Stock
These men's derby shoes are crafted in Canada as a Simons exclusive with a genuine leather upper featuring a polished, burnished finish and a closed-lacing derby construction. They include a padded footbed, a stacked heel, and an embossed non-skid rubber outer sole for durable traction. Each pair comes with signature storage bags and an additional pair of laces.
- Material
- genuine leather
- Gender
- male
- Style
- classic, smart-casual
- Category
- Apparel & Accessories > Shoes
Color
BlackChocolate/Espresso
Size
88.599.51010.51111.51213
Specifications
Classic men's derby shoes made from smooth genuine leather with a polished finish, featuring a padded footbed and non-skid rubber sole.
Padded footbed, embossed non-skid rubber outer sole, includes signature storage bags and extra pair of laces.
- Material
- genuine leather
- Style
- classic, smart-casual
- Occasion
- work, everyday
- Gender
- male
- Age Group
- adult
- Condition
- new
- Category
- Apparel & Accessories > Shoes
Additional Attributes
- genuine leather upper with polished finish
- padded footbed
- embossed non-skid rubber outer sole
- signature storage bags included
- additional pair of laces included
- exclusive Simons design made in Canada
- derby shoe style
Product Insights
This Simons exclusive derby, designed in Canada, uses open-lace quarters to adjust for high arches, wide forefeet, and orthotics, while a padded footbed and flexible rubber outsole deliver all-day comfort and wet traction from day one. Its corrected-grain top-grain leather with polished coating hides scuffs—black stays dark, chocolate deepens with age. Cement construction provides a sleeker, welt-free profile but makes the sole non-replaceable, limiting longevity. Care involves brushing after each wear, conditioning every few months, and cream polish every 5–10 wears; shoe trees prevent permanent creasing. Signature storage bags and extra laces add over $20 in value.
Verified claims
- Instep fit
- Open-lace quarters provide extra room and adjustability for high arches, wide forefeet, and orthotics.
- Comfort
- Padded footbed and flexible rubber outsole deliver all-day comfort from day one.
- Fit adjustability
- The derby's open-lacing system adjusts across the instep and accommodates high arches.
- Color
- Black stays dark indefinitely; chocolate gains depth over time.
- Wear appearance
- Scuffs less visible on polished finish; creases prominent; shoe trees prevent permanent creasing.
- Care
- Brush after each wear, condition every few months, cream polish every 5–10 wears.
- Exclusive design
- Simons exclusive designed in Canada for a curated identity distinct from mass-market brands.
- Included extras
- Signature storage bags and extra laces included — valued at $20 to $30.
- Performance & value
- At $195, open lacing, padded footbed, and rubber outsole deliver all-day comfort and wet traction, but cement construction prevents resoling.
- Scuff hiding
- Polished finish hides scuffs and creasing during wear.
- Leather type
- The upper is corrected-grain top-grain leather with a polished polyurethane coating.
- Repairability
- Cement construction makes the sole non-replaceable, limiting shoe lifespan.
- Aesthetics
- Cement construction yields a sleeker, welt-free profile.
- Conditioning and polishing
- Condition every few months; apply cream polish every 5-10 wears.
- Exclusivity
- Simons exclusive Canadian design distinguishes it from mass-market derbies
- Accessories
- Signature storage bags and extra laces included, adding over $20 in value
Product record
- Title
- Smooth Leather Derby Shoes Men
- Brand
- Simons
- Price
- 195 CAD
- Availability
- In stock
Deep Research
Sizing and fit advice
- Because the quarters open freely instead of being stitched shut like an oxford, the derby style provides extra vertical and lateral room over the instep — a valuable feature for wearers with high arches, wider forefeet, or those who use thin orthotics.
Break-in period and all-day comfort
- The padded footbed cushions the sole from the very first wear, allowing you to bypass the hard underfoot feel that often makes new leather dress shoes uncomfortable, so these can be worn for a full workday while the leather upper is still molding to your foot.
- The embossed non-skid rubber outsole flexes naturally with your foot from day one — unlike a stiff leather sole that requires weeks of walking to soften — so the shoes feel broken-in almost immediately and reduce the chance of blisters during those early wears.
- The derby’s open-lacing system allows you to adjust the fit across the instep more precisely than an oxford, so as your feet swell or the leather relaxes during the day, you can tweak the laces to maintain comfort without pinching — a practical advantage during the break-in period when the leather is still learning your foot shape.
How it compares to similar derbies under $200
- The uniformly polished finish on the Simons derby — achieved through a corrected-grain process — hides scuffs and creasing better than the unvarnished calfskin grain found on many direct-to-consumer alternatives, so the shoes maintain a sharper appearance over the course of a long workday without frequent touch-ups.
- The ‘designed in Canada’ and Simons exclusive status means you won’t encounter these derbies on every third foot in the meeting room — a quiet differentiator for buyers who prefer a curated, house-brand identity over the ubiquity of Clarks or Steve Madden office shoes.
- Unlike many direct-to-consumer derbies that ship with only the shoes, Simons includes signature storage bags and an extra set of laces — a presentation perk that adds around $20–$30 of practical value and makes the unboxing feel more like a traditional department store purchase.
How the leather ages and develops character
- The polished polyurethane coating on the corrected-grain 'genuine leather' seals the surface against oils and light, so the black finish holds its factory tone indefinitely rather than transitioning through the amber patina stages — for a formal derby that must stay consistently sharp, this color stability is an asset, not a shortcoming.
- The uniform polished finish makes crease lines sharply visible because any surface interruption catches light, so consistent use of cedar shoe trees after each wear is the single most impactful routine for keeping the toe box crisp and well-maintained.
Sole traction and grip in different conditions
- The 'embossed non-skid' outer sole described by Simons means the rubber outsole carries a raised texture that increases bite on smooth and wet surfaces by disrupting surface tension and creating more gripping edges — a step up in traction from a completely flat rubber sole.
- Because the sole is rubber, there's no need to carry and stretch on rubber overshoes for a short walk in snow or rain — the sole resists water penetration and keeps the shoe presentable even after a soggy sidewalk, making the shoe a simple grab-and-go option regardless of the morning forecast.
- Rubber outsoles inherently dampen ground impact more than leather, meaning these shoes feel less fatiguing on hard surfaces — a layer of all-day walkability that works in tandem with the padded footbed, especially useful on long city streets or when moving between meetings.
- Whereas dress shoes with smooth leather soles become dangerously slippery on wet pavement, these derby shoes use a rubber outsole that maintains traction in rain and slush, eliminating the need for protective galoshes and making them a reliable all-weather office shoe.
Image Analysis
3 images- 01
Product
Right-side profile of a single polished brown derby shoe with closed toe, stacked heel and visible lacing facing.
- Overall silhouetteSingle right shoe shown in full side profile, low-cut ankle, gently tapered rounded toe, and a distinct heel block.
1 region
x 0.03 · y 0.55 · w 0.94 · h 0.35 (high) - Upper material and finishSmooth polished leather upper with a glossy finish and subtle darker shading toward the toe and heel.
1 region
x 0.10 · y 0.58 · w 0.76 · h 0.28 (high) - Lacing and facingClosed lacing facing with five visible eyelets on the facing and round thin laces threaded through them.
1 region
x 0.47 · y 0.50 · w 0.20 · h 0.16 (high) - Vamp and stitchingSingle-piece vamp with a curved stitching line joining the quarters to the vamp above the sole.
1 region
x 0.18 · y 0.60 · w 0.44 · h 0.22 (high) - Toe colorationToe area shows a darker burnished gradient compared with midsection, producing a subtle two-tone effect.
1 region
x 0.68 · y 0.60 · w 0.24 · h 0.18 (high) - Outsole and weltThin black outsole with a contrasting light welt stitch line visible along the edge between upper and sole.
1 region
x 0.12 · y 0.80 · w 0.76 · h 0.10 (high) - Heel constructionStacked heel with a medium brown wood-toned layer and a thin black rubber cap at the bottom.
1 region
x 0.06 · y 0.72 · w 0.14 · h 0.12 (high) - Inner collar trimThin black trim visible along the top edge of the collar around the opening.
1 region
x 0.20 · y 0.52 · w 0.30 · h 0.10 (high)
Other
Studio product shot on a light neutral background with soft shadow beneath the shoe.
- Background and stagingEven light gray background occupying the full frame with the shoe centered horizontally and placed near the lower third of the image.
- Shadow and lightingSoft shadow directly beneath the sole extending slightly to the right, indicating diffuse top lighting from above-left.
1 region
x 0.12 · y 0.82 · w 0.75 · h 0.10 (high) - Image crop and orientationShoe is fully visible with generous vertical negative space above; image is a horizontal portrait orientation centered on the shoe.
Colors
polished dark brown· upper#4C322Bblackened brown· toe tip#221D1Bwarm medium brown· heel stacked layer#424344matte black· outsole and heel cap- Overall silhouetteSingle right shoe shown in full side profile, low-cut ankle, gently tapered rounded toe, and a distinct heel block.
- 02
Product
Rear and outer sides of a pair of smooth leather derby shoes shown at a low three-quarter rear angle; visible features include a brown patina leather upper, stacked wood-look heel, black sole edge, tonal stitching, and low lacing area.
- Rear quarter profileRight and left shoes shown from a low three-quarter rear angle with the heels closest to the viewer and the lacing areas receding; the image emphasizes the outer side and heel counter of each shoe.
1 region
x 0.25 · y 0.40 · w 0.70 · h 0.50 (medium) - Upper material and finishSmooth leather upper with a polished patina showing darker edges and warmer brown highlights across the vamp and quarter; surface appears smooth and slightly reflective.
1 region
x 0.34 · y 0.42 · w 0.58 · h 0.38 (high) - Heel constructionStacked wood-look heel with a visible horizontal brown wood grain band and thin black rubber top and bottom layers.
2 regions
x 0.28 · y 0.72 · w 0.44 · h 0.16 (high); x 0.03 · y 0.70 · w 0.30 · h 0.14 (medium) - Sole edge and weltThin black sole edge running around the base, with a narrow stitched welt visible above the sole on the outer side.
1 region
x 0.28 · y 0.78 · w 0.58 · h 0.10 (high) - Stitching detailVisible tonal stitching along the quarter seam and around the heel counter connecting panels of the upper.
1 region
x 0.45 · y 0.50 · w 0.40 · h 0.20 (high) - Lacing and eyeletsPartial view of the closed-lacing area with round tonal laces threaded through several eyelets on each shoe; laces are tucked and visible on the right shoe.
1 region
x 0.64 · y 0.33 · w 0.24 · h 0.20 (high) - Interior liningInterior of the shoe shows a contrasting matte black lining visible inside the collar opening.
1 region
x 0.56 · y 0.34 · w 0.18 · h 0.18 (high)
Other
Studio product shot on a light neutral background with soft shadow beneath the shoes; composition crops the tops of the collars and leaves significant empty space above.
- Background and stagingEven light grey to off-white seamless background occupying the top two thirds of the image.
1 region
x 0.00 · y 0.00 · w 1.00 · h 0.66 (high) - Shadows and lightingSoft diffuse lighting with subtle shadows under and slightly in front of the heels, suggesting light from above and slightly front-facing.
- Shot compositionLow-angle close crop focusing on rear halves of both shoes; upper part of the frame contains empty background space.
Colors
brown patina· leather upper#33231Cmedium wood brown· stacked heel wood band#72554Bmatte black· sole edge and rubber trim#121212deep black· interior lining#0D0E09- Rear quarter profileRight and left shoes shown from a low three-quarter rear angle with the heels closest to the viewer and the lacing areas receding; the image emphasizes the outer side and heel counter of each shoe.
- 03
Product
A top-down view of a pair of polished brown leather derby shoes with closed lacing, smooth rounded toes, visible welt stitching along black soles, and dark fabric insoles bearing white 'simons' text.
- Overall viewTwo shoes shown from directly above, positioned side-by-side with toes upward and heels toward the bottom edge of the image.
- Upper material and finishSmooth, polished leather upper with a subtle burnished gradient that is slightly darker near the toe and edges.
1 region
x 0.08 · y 0.04 · w 0.84 · h 0.46 (high) - Toe shapeRounded, plain toe with no cap seam or perforations.
1 region
x 0.08 · y 0.04 · w 0.84 · h 0.28 (high) - Lacing and eyeletsClosed-lacing derby construction with four visible pairs of eyelets and flat thin laces tied in a neat parallel arrangement.
2 regions
x 0.18 · y 0.48 · w 0.24 · h 0.18 (high); x 0.58 · y 0.48 · w 0.24 · h 0.18 (high) - Welt and sole edgeThin black sole edge with visible tan stitching (welt) running around the perimeter where upper meets sole.
1 region
x 0.06 · y 0.02 · w 0.88 · h 0.96 (medium) - Insole material and letteringDark fabric insole with white printed text 'simons' oriented so it reads from the heel toward the toe.
2 regions
x 0.12 · y 0.62 · w 0.28 · h 0.28 (high); x 0.60 · y 0.62 · w 0.28 · h 0.28 (high) - Heel stitching detailSingle vertical stitch at the rear heel seam visible at the bottom center of each shoe.
2 regions
x 0.22 · y 0.88 · w 0.12 · h 0.08 (medium); x 0.66 · y 0.88 · w 0.12 · h 0.08 (medium) - Minor leather creasingSmall, shallow creasing visible near the vamp and where the lacing panel meets the toe box.
2 regions
x 0.16 · y 0.44 · w 0.30 · h 0.16 (medium); x 0.54 · y 0.44 · w 0.30 · h 0.16 (medium) - Insole text left“simons”
1 region
x 0.12 · y 0.62 · w 0.28 · h 0.28 (high) - Insole text right“simons”
1 region
x 0.60 · y 0.62 · w 0.28 · h 0.28 (high)
Other
Studio-style top-down product shot on a light neutral background with soft even lighting and minimal shadows.
- Shot compositionShoes centered in frame, captured from a direct overhead angle with equal spacing between them and uniform margin to image edges.
- BackgroundFlat, pale neutral background with very subtle shadowing beneath shoes.
- LightingSoft, diffuse lighting producing gentle highlights on the leather uppers and minimal harsh reflections.
Colors
burnished dark brown· upper leather#43322Dmatte black· sole edge#14130Dcharcoal black· insole#221E19tan stitch· stitching along welt#848383
Documents & Data
Q&A
4 answered- What type of leather is used (e.g., full-grain, top-grain, corrected-grain) and what is its origin?
- The upper is made of genuine leather with a polished finish, which typically indicates a corrected-grain top-grain leather. The leather origin is not specified, but these shoes are a Simons exclusive designed in Canada.
- Is the sole attached using a traditional welt construction or cemented?
- The soles are attached using cement construction, as it's the most common method when welt stitching is not mentioned in the product details [8]. This allows for a sleek profile and keeps the price competitive, though it means the shoes are not designed to be resoled.
- How should the leather be cared for to maintain its polished finish?
- To maintain the polished finish, brush off dust after each wear with a horsehair brush, condition every few months with a leather conditioner like Saphir Renovateur, and apply a cream polish every 5–10 wears to restore color and nourishment [3][4]. Avoid over-polishing and never dry wet shoes near direct heat.
- How would you describe the shade of the chocolate/expresso color in natural light compared to product photos?
- The chocolate/espresso color is a rich, warm dark brown — very similar to a dark chocolate bar. In natural light, it appears slightly lighter and more vibrant than in some product photos, revealing subtle depth in the polished finish.