Simons
Leather Chelsea Boots Men
These men's Chelsea boots are ankle-height leather footwear with side elastic gussets and a rear pull loop for slip-on entry. They feature a genuine leather upper, padded footbed with a leather top cover, and a non-skid embossed outer sole; signature storage bags are included. Designed in Canada as a Simons exclusive, the black leather boots are intended for everyday wear.
- Material
- Genuine leather upper; side elastics; padded footbed with a leather top cover; non-skid embossed outer sole
- Gender
- male
- Style
- classic
- Category
- Apparel & Accessories > Shoes
Color
Specifications
Men's genuine leather Chelsea boots with side elastic panels and a padded leather-covered footbed.
Genuine leather upper, side elastic gussets, padded footbed with leather top cover, back pull loop, non-skid embossed outer sole, and signature storage bags included.
- Material
- Genuine leather upper; side elastics; padded footbed with a leather top cover; non-skid embossed outer sole
- Style
- classic
- Occasion
- everyday, casual
- Gender
- male
- Age Group
- adult
- Condition
- new
- Category
- Apparel & Accessories > Shoes
Additional Attributes
- genuine leather upper
- Chelsea boot silhouette
- side elastic gussets
- back pull loop for easy on/off
- padded footbed
- leather top cover on footbed
- non-skid embossed outer sole
- signature storage bags included
- Simons exclusive design
- designed in Canada
- men's specific style
- slip-on pull-on construction
- ankle-height Chelsea boot profile
Product Insights
Leather Chelsea Boots Men 295 CAD Size up if your foot measures between two sizes Side elastic gussets act as the closure and widen the opening for entry Clean with a damp cloth, condition regularly, protect from water and store in the dust bag Only Black is offered, with no colourway choice
Verified claims
- category
- Men's Chelsea boot in black leather
- sizing
- Sizes 8–13, with half sizes from 8 to 12 and a full-step 12 to 13
- fit
- Size up if your foot measures between two sizes
- fit
- Aim for snug ankle and instep with a roomy toe box
- construction
- Side elastic gussets act as the closure and widen the opening for entry
- comfort
- Leather moulds and elastic relaxes, so initial snugness can ease
- fit
- Test gusset tension: it should hold without digging in or allowing heel lift
- material
- Upper is genuine leather, not a full-grain claim
- material
- Leather lining and sock with a padded leather-top footbed
- comfort
- Padded leather footbed helps manage moisture and friction
- construction
- Elastic side panels, rear pull loop, non-skid embossed sole
- construction
- Low stacked heel, welted sole edge, studded rubber tread and tan midsole insert
- styling
- Sleek black silhouette with smooth polished leather and slim rounded toe
- use
- Versatile for smart-casual, office, evening and city wear
- options
- Only Black is offered, with no colourway choice
- value
- 295 CAD flat across sizes, with no large-size premium
- care
- Clean with a damp cloth, condition regularly, protect from water and store in the dust bag
- durability
- Leather can outlast the elastic gores, which have a limited service life
- care
- Proper fit and shoe trees keep flex creases shallow
- comparison
- Laceless Chelsea convenience versus less adjustability than lace-ups or side zips
Product record
- Title
- Leather Chelsea Boots Men
- Brand
- Simons
- Price
- 295 CAD
- Availability
- In stock
Buying Guide
1 comparison · 10 sourcesUses
Slip them on quickly with the back pull loop
These leather Chelsea boots have a fabric pull loop at the top rear of the shaft that you can grab to help pull them on. According to Simons, the back pull loop is intended for easy on, handy when you're stepping out and don't want to fuss with laces or zippers.[1,3]
Keeping leather boots conditioned and protected from moisture
Leather naturally dries out over time, and without regular conditioning it can eventually crack and stiffen. Moisture protection matters too, since water damage is a common cause of premature wear in leather dress shoes. Conditioning and protecting these Chelsea boots helps support the leather through regular wear.[2]
Product comparison
Compared within this brand.
| Leather Chelsea Boots Men: Choose this if you want a Simons-exclusive Chelsea boot designed in Canada, in black polished leather with elastic side gussets, a back pull loop intended for easy on, and a padded footbed with a leather lining and sock. It comes in sizes 8 through 13, has an embossed non-skid outer sole, and signature storage bags are included. As with any leather footwear, keep in mind that leather needs regular conditioning and moisture protection to avoid cracking or water damage, and the exact outer-sole material is unspecified.[1,2,4] | Sigrid Square-Toe Boots Men: Choose this if you want a mid-calf black boot with a square toe and an inner-side zip, offered in European sizes 40 through 45 in Black or Brown. It pairs a leather upper with a padded footbed, low stacked block heel, and a non-skid embossed outer sole, and includes a signature dust bag. Note that while the listing describes a genuine leather lining, the composition breakdown lists the lining and sock as textile.[5,6] | Sergio Western Boots Men: Choose this if you want a Simons-exclusive, Canadian-designed western boot with a genuine leather upper, a decorative harness strap with metal ring and studs, and an inner-side zip for easy on and off. The padded footbed, non-skid embossed outer sole, and 2.25-inch (6 cm) stacked block heel with a pointed toe suit everyday wear with a western edge, and each pair is made in Portugal with a signature dust bag included. Note that the lining and sock are listed as other materials rather than leather.[7,8,9,10] |
Image Analysis
3 images- 01
Product
Right-side profile of a single black Chelsea boot showing smooth leather upper, elastic side panel, rear pull tab, low stacked heel, and slim rounded-toe sole.
- Overall silhouetteSingle right-boot shown in full profile (outer lateral side) with a mid-ankle shaft, tapered rounded toe, and low stacked heel.
1 region
x 0.06 · y 0.45 · w 0.88 · h 0.38 (high) - Upper materialSmooth, slightly glossy leather surface covering the vamp and shaft with very subtle natural sheen and minimal visible texture.
1 region
x 0.16 · y 0.48 · w 0.66 · h 0.29 (high) - Elastic side panelVertical elastic gore inset on the lateral side, rectangular with rounded corners and stitched perimeter, set between vamp and rear quarter.
1 region
x 0.11 · y 0.47 · w 0.18 · h 0.24 (high) - Pull tabFabric pull loop attached at the top rear of the shaft protruding upward.
1 region
x 0.08 · y 0.41 · w 0.04 · h 0.06 (high) - Stitching and seamSingle visible vertical seam at the rear quarter connecting upper panels and neat topstitching around the elastic panel.
1 region
x 0.16 · y 0.63 · w 0.10 · h 0.11 (high) - Heel and sole constructionLow stacked block heel with a slightly textured side, thin welt and a flat sole profile that tapers up slightly at the toe.
1 region
x 0.06 · y 0.72 · w 0.62 · h 0.12 (high)
Other
Studio product shot on a light neutral background with soft even lighting producing minimal shadow beneath the sole; shoe centered horizontally and cropped with roomy top margin.
- Background and stagingEven light gray background occupying whole frame with no additional props.
- ShadowSoft diffuse shadow directly beneath the sole and heel extending slightly forward, indicating downward lighting.
1 region
x 0.18 · y 0.80 · w 0.68 · h 0.06 (medium) - Image crop and compositionShoe is centred horizontally in the lower half of the image with ample empty space above the shaft.
Colors
black· leather uppermatte black· elastic side panelblack· pull tabblack· heel and sole- Overall silhouetteSingle right-boot shown in full profile (outer lateral side) with a mid-ankle shaft, tapered rounded toe, and low stacked heel.
- 02
Product
Close-up rear and lateral view of a black leather Chelsea boot showing the heel, elastic side panel, pull tab, stitching and the sole of the second boot lying on its side.
- Upper materialSmooth glossy black leather upper visible on the rear and side of the boot with a subtle shine and even surface.
1 region
x 0.45 · y 0.22 · w 0.48 · h 0.66 (high) - Elastic side panelVertical black elastic gusset on the ankle side, inset between leather panels and framed by visible stitching.
1 region
x 0.68 · y 0.32 · w 0.17 · h 0.46 (high) - Heel constructionLow stacked-style heel with horizontal layering texture in a matte black finish, attached to the sole with a thin welt visible above the heel.
1 region
x 0.52 · y 0.73 · w 0.28 · h 0.20 (high) - Pull tabBlack woven pull tab at the top rear of the boot with visible horizontal ribbing, projecting upward.
1 region
x 0.53 · y 0.12 · w 0.06 · h 0.12 (high) - Back seam and stitchingVertical back seam with single line of visible stitching running down the center rear of the boot and additional topstitching where panels join.
1 region
x 0.50 · y 0.27 · w 0.10 · h 0.44 (high) - Second boot sole detailSole of the second boot shown lying on its side with a patterned rubber tread featuring round traction studs and a contrasting tan midsole insert.
1 region
x 0.04 · y 0.45 · w 0.50 · h 0.36 (high) - Sole text emboss“simons”
1 region
x 0.18 · y 0.60 · w 0.12 · h 0.16 (medium)
Other
Studio-style close-up on a light neutral background showing two boots (one upright, one on its side); soft even lighting with a short shadow under the soles.
- Shot compositionTwo boots arranged so the rear and lateral side of one boot faces the camera while the other lies on its side to show the sole; image cropped to focus on the lower two-thirds of the frame.
- Background and surfaceUniform pale gray background and surface with no visible props or textures.
- Lighting and shadowSoft diffuse lighting produces mild highlights on the leather and a short soft shadow beneath the boots toward the front of the frame.
Colors
gloss black· leather uppermatte black· elastic side paneldark charcoal· stacked heeltan leather· sole mid-insert- Upper materialSmooth glossy black leather upper visible on the rear and side of the boot with a subtle shine and even surface.
- 03
Product
A pair of black leather Chelsea boots shown from a low three-quarter/front angle; smooth polished uppers with elastic side gussets, pull tabs at the rear, low stacked heels and welted sole edges are visible.
- Overall compositionTwo Chelsea boots shown together: the left shoe is placed slightly forward and left, the right shoe sits behind and to the right, both angled so the outer sides and toes are visible.
1 region
x 0.02 · y 0.25 · w 0.96 · h 0.66 (high) - Upper material and finishSmooth, polished black leather uppers with a reflective sheen and even surface; highlights indicate a high-gloss finish.
1 region
x 0.04 · y 0.42 · w 0.68 · h 0.43 (high) - Toe shapeElongated, slightly pointed rounded toe profile on both shoes.
2 regions
x 0.06 · y 0.60 · w 0.58 · h 0.31 (high); x 0.52 · y 0.54 · w 0.40 · h 0.33 (high) - Elastic side gussetsVertical elastic panels on the outer side of each boot in a matte black fabric contrasting slightly with the polished leather.
2 regions
x 0.05 · y 0.21 · w 0.20 · h 0.36 (high); x 0.46 · y 0.18 · w 0.17 · h 0.36 (high) - Pull tabsNarrow fabric pull tabs extending above the boot collar at the back of each shoe.
2 regions
x 0.06 · y 0.12 · w 0.06 · h 0.12 (high); x 0.42 · y 0.08 · w 0.05 · h 0.14 (high) - Sole and weltThin welt visible where upper meets sole; low stacked heel with a slightly glossy finish distinct from the upper.
2 regions
x 0.03 · y 0.73 · w 0.64 · h 0.18 (high); x 0.55 · y 0.64 · w 0.36 · h 0.21 (high) - Stitching and seamsVisible topstitching outlining the elastic gusset and seams at the heel counter; stitching is narrow and matches the boot color.
1 region
x 0.04 · y 0.20 · w 0.20 · h 0.36 (medium)
Other
Product photographed on a plain light gray background with soft overhead lighting that creates specular highlights and soft shadows under the shoes; image is centered and sharply focused.
- Background and stagingUniform light gray background filling the frame, no props or packaging visible.
- Lighting and reflectionsSoft directional lighting from above-left producing clear highlights along the toe boxes and subtle, soft shadows beneath and to the right of the shoes.
- ShadowsSoft diffuse shadow under each shoe, darker beneath the forefoot areas, indicating separation from background surface.
1 region
x 0.20 · y 0.74 · w 0.62 · h 0.16 (medium) - Image qualityHigh resolution with sharp detail on leather texture and stitching; no visible noise or compression artifacts.
Colors
gloss black· upper leather#0E0E0Dmatte black· elastic side gussets#191916dark black· sole and heel#0E0E0E- Overall compositionTwo Chelsea boots shown together: the left shoe is placed slightly forward and left, the right shoe sits behind and to the right, both angled so the outer sides and toes are visible.
Variants
10 SKUs| SKU | Title | Price | Avail |
|---|---|---|---|
| 4745100 | Leather Chelsea Boots Men - Black - 8 | CA$295.00 | Yes |
| 4745101 | Leather Chelsea Boots Men - Black - 8.5 | CA$295.00 | Yes |
| 4745102 | Leather Chelsea Boots Men - Black - 9 | CA$295.00 | Yes |
| 4745103 | Leather Chelsea Boots Men - Black - 9.5 | CA$295.00 | Yes |
| 4745104 | Leather Chelsea Boots Men - Black - 10 | CA$295.00 | Yes |
| 4745105 | Leather Chelsea Boots Men - Black - 10.5 | CA$295.00 | Yes |
| 4745106 | Leather Chelsea Boots Men - Black - 11 | CA$295.00 | Yes |
| 4745107 | Leather Chelsea Boots Men - Black - 11.5 | CA$295.00 | Yes |
| 4745108 | Leather Chelsea Boots Men - Black - 12 | CA$295.00 | Yes |
| 4745109 | Leather Chelsea Boots Men - Black - 13 | CA$295.00 | Yes |