Chicago High-Tops
Many of our styles are available in both women's and men's sizing. To compare both sizing options, enter the product name in the search bar.
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The Chicago High-Top takes our chunky retro sneaker and runs it up over the ankle — that late-90s dad-shoe silhouette with a bit more attitude and a lot more support. The pair for when you want presence underfoot and a sneaker that makes a statement of its own.
The look is built on contrast: clean panels of our Italian bio-based vegan leather (62–66% plant-origin materials) broken up with breathable mesh through the sides and ankle, so they've got the layered, technical face of a proper high-top runner — an all-white pair that stays clean and versatile against jeans, joggers or shorts. The leather's water-resistant and wipes clean, which counts on a white shoe you'll actually live in. Metal eyelets and lace tips in 100% zamak (a durable zinc alloy) run the lacing right up the ankle, and there's an embroidered WVS pull tab on the tongue for pulling them on.
The high collar is where these earn their keep — wrapped in padding that cushions and supports the ankle, so they feel locked in rather than loose. Underneath, a chunky TR outsole with a light tread is sculpted for shock absorption and lift, sitting you up on a 4.5cm heel and 2.5cm toe. It's got the stance but stays light and flexible, and cushioned layered insoles — soft memory foam over a recycled PU base (20% recycled PU) — keep them comfortable from morning to night.
Inside, soft Tencel™ linings run the length of the shoe — breathable, moisture-wicking, and comfortable enough to wear with socks or without.
This product is certified carbon-neutral and ethically made in Portugal under EU employment, discrimination and health & safety law. It's vegan from the uppers and linings to the glue. It's delivered to you through our carbon-neutral supply chain in plastic-free paper and cardboard packaging.
- Upper
- Italian bio-based vegan leather (62–66% plant-origin materials)
- Lining
- Portuguese vegan suede (100% PU) – soft and comfortable against the foot, with a breathable suede texture that helps keep feet fresh
- Insole
- Cushioned layered insole – a soft memory foam top layer over a recycled PU base (20% recycled PU) cut to fit the shoe
- Outsole
- Flexible TR outsole with a light tread for grip
- Laces
- Long, extra-strong laces (100% recycled polyester), with metal lace tips (100% zamak — a durable zinc alloy)
- Shank
- Steel shank for stability and support through the arch
- Hardware
- Metal eyelets and lace tips — both 100% zamak (a durable zinc alloy)
- Construction
- Mounted (cemented) construction – the upper is lasted to shape and the outsole bonded directly underneath. The most widely used construction method in footwear, it gives a clean, flexible build, though the outsole isn't easily resoled
- Water Resistance
- Water-resistant for everyday wear – keeps you dry in rain, puddles, wet streets, and most winter conditions. Just avoid heavy saturation or full submersion.
- Width
- D width fitting – a slightly wider fit with more volume than standard
- Fit
- Order your usual size. Half size? Wider width fittings size up, narrower width fittings size down.
- Heel Height
- 4.5 cm
- Toe Height
- 2.5 cm
- Toe Shape
- Round toe
- Instep
- Flat insole through the arch
- Break-in Time
- You should find these comfy straight out of the box.
- Type
- Trainers
- Closure
- Lace-up
- Gender
- Men's
- Made In
- Portugal
- Weight
- 2.29 kg per pair
Women's
| EU Size | Foot Length (mm) |
|---|---|
| 36 | 227 |
| 37 | 233 |
| 38 | 240 |
| 39 | 247 |
| 40 | 253 |
| 41 | 260 |
| 42 | 267 |
Men's
| EU Size | Foot Length (mm) |
|---|---|
| 40 | 253 |
| 41 | 260 |
| 42 | 267 |
| 43 | 273 |
| 44 | 280 |
| 45 | 287 |
| 46 | 293 |
| 47 | 300 |
| 48 | 307 |
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These shoes are so great.
One of the shoes has the sole coming away already. Usually had good experience with Will's vegan shoes (had 3 pairs of different shoes previously) but not woth this pair.
Hi Miles,
I wanted to personally reach out to get in touch, I am really sorry to hear about the problems with your purchase and that they did not perform as you would expect.
We will always refund, replace or try to repair any purchase if you are not happy at any point - just let us know and we always take care of our customers.
You can reach me on my direct email for any assistance on wg@wills-vegan-shoes.com
I have sent you a message to help you further.
Please let me know if I can be any more help at all,
Will
Love the Chicago black tops! Will be getting them in white as well 😊.
Great quality, love the look and very comfortable
These are the best High Tops I've ever owned and they're vegan. Can't beat that.