Drew Men's Jimmy Shoes

Name: Drew Men's Jimmy Shoes
Brand: Drew
Availability: OutOfStock

Removable footbed for custom orthotics

Size Size Chart

Width

Available for $329

Why shop with us:

Money back guarantee: 30-day returns & exchanges
Canadian owned and operated
Secure payment with enhanced protection
Multiple payment options available

Plus Fitting System® - Two Removable Footbeds for Added and Double Depth
Removable, Polyurethane, Drilex® Lined Insole
Breathable, Soft Fabric Lining and Leather Upper
Durable Rubber Outsole and EVA Midsole
Dual Shank System
Wide, Synthetic Fiber Shank
External TPU Shank
Firm Heel Counter
Rocker Bottom
Soft, Foam-padded Tongue and Collar
Accommodates Prescribed Orthotics
Covered by most insurance plans

Drew® Jimmy shoes combine the ease of two hook and loop closures with an athletic style. These Drew adjustable leather shoes offer the proprietary Plus Fitting System® with two removable insoles plus all the therapeutic benefits Drew is famous for including shock-absorbing inserts, flared outsoles and firm heel counters. So don't settle for just any walking shoe – choose the Drew Jimmy for superior comfort.

Plus Fitting System® - Two Removable Footbeds for Added and Double Depth
Removable, Polyurethane, Drilex® Lined Insole
Breathable, Soft Fabric Lining and Leather Upper
Durable Rubber Outsole and EVA Midsole
Dual Shank System
Wide, Synthetic Fiber Shank
External TPU Shank
Firm Heel Counter
Rocker Bottom
Soft, Foam-padded Tongue and Collar
Covered by most insurance plans
Model 44935

Shipping & Returns

Shipping

Free door-to-door shipping on orders over $99 across Canada
Standard shipping fee: $14.99 for orders under $99
Orders are processed within 2–5 business days
Estimated delivery: 2–7 business days depending on your location

Easy Returns

30-day money-back guarantee on all purchases
Items must be unworn, in original undamaged packaging
Prior return authorization is required — contact us before shipping
Refunds are processed within 5–10 business days after we receive the item

Frequently Asked Questions

Do Drew shoes work with custom orthotic insoles?

Yes. All Drew shoes feature removable insoles and extra depth, allowing you to use your own custom orthotic inserts. This is one of the brand's key advantages for people with specific foot health needs.

What sizes and widths are available in Drew shoes?

Drew offers one of the widest size/width ranges in the industry. Men's widths: Narrow (B), Medium (D), Wide (2E), 4W (4E), and 6E. Women's widths: Slim (4A), Narrow (2A), Medium (B), Wide (D), WW (2E), and XW (4E). Some styles may vary — check the specific model listing for details.

What foot conditions are Drew shoes designed for?

Drew specializes in therapeutic and orthopedic footwear suitable for diabetes, plantar fasciitis, arthritis, bunions, hammertoes, flat feet (pes planus), high arches (pes cavus), and other foot conditions. Features like deep toe boxes, firm heel counters, and cushioned midsoles provide targeted support.

How do I care for my Drew shoes?

For full grain leather: wash with a damp cloth and mild soap, apply a matching cream polish, let it sit for a few minutes, then buff with a soft cloth or brush. Always test cleaning products on an inconspicuous area first. Avoid storing shoes in a closed box for extended periods, especially in humid climates.

Are Drew shoes available in Canada?

Drew does not ship directly outside the USA. However, the brand has authorized distributors and retailers across Canada. You can find a local store using the Drew Shoe Store Locator on their website, or visit us at Comfort Clinic in Oakville.