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Gambit Double-Monk

$150
$369
Final Sale ?

Final Sale:
All sales final, no returns, no exchanges. Final sale items mailed back to Wolf & Shepherd will be issued store credit. Wolf & Shepherd will exchange or refund any damaged or defective items.

Exchange Only:
Items may be exchanged or returned for store credit. No refunds will be issued.

Full Priced Items:
Full priced items are eligible for return for 30 days and exchange for 60 days. Returns and exchanges are available to US customers only. Items must be in original packaging and unworn to be eligible. To begin a return or exchange, please click here. (to be linked)

Select accessories are all final sale due to hygiene. This includes:
- Socks
- Hats
- Shoe Care items including: creams, waxes, sprays, and Care Kits
- Shoe Trees
- Shoe Horns

Wolf & Shepherd will exchange or refund any damaged or defective items.

Regular price
107 reviews

Gambit Double-Monk

$150
$369
Final Sale ?

Final Sale:
All sales final, no returns, no exchanges. Final sale items mailed back to Wolf & Shepherd will be issued store credit. Wolf & Shepherd will exchange or refund any damaged or defective items.

Exchange Only:
Items may be exchanged or returned for store credit. No refunds will be issued.

Full Priced Items:
Full priced items are eligible for return for 30 days and exchange for 60 days. Returns and exchanges are available to US customers only. Items must be in original packaging and unworn to be eligible. To begin a return or exchange, please click here. (to be linked)

Select accessories are all final sale due to hygiene. This includes:
- Socks
- Hats
- Shoe Care items including: creams, waxes, sprays, and Care Kits
- Shoe Trees
- Shoe Horns

Wolf & Shepherd will exchange or refund any damaged or defective items.

Regular price
107 reviews
Colorway Onyx 3 colorways
Size Ruler What size am I?
Size Ruler What size am I?
    • All-Day Comfort For Your Feet
    • Premium Italian Leather
    • Full-grain Italian calfskin upper
    • Ultra soft, abrasion-resistant sheepskin lining
    • Leather treated with custom-blended formula to improve softness and durability
    • FloatForm memory foam throughout footbed for industry-leading comfort
    • Heel-to-toe ratio optimized for posture and support
    • Padded heel and tongue for a glove-like fit
    • High-traction resoleable rubber and leather outsole
  • Runs true to size. Take your true dress shoe size for a comfortable, glove-like fit. These will give with time and mold to the shape of your foot.

    Note: Most sneakers run about a half size small, meaning someone who wears a 10 in dress shoes often prefers a 10.5 in sneakers. We recommend looking at your previous dress shoes to best gauge your size.

    • Tailored suit
    • Slacks and a jacket
Explore the Gambit Double-Monk
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Size Guide

Shoe Size Guide
U.S. Size EU Size U.K. Size Canadian Size Inches
6 39 5 6 9.25
6.5 39.5 5.5 6.5 9.42
7 40 6 7 9.625
7.5 40.5 6.5 7.5 10
8 41 7 8 10.4
8.4 41.5 7.5 8.5 10.125
9 42 8 9 10.25
9.5 42.5 8.5 9.5 10.5
10 43 9 10 10.625
10.5 43.5 9.5 10.5 10.75
11 44 10 11 11
11.5 44.5 10.5 11.5 11.125
12 45 11 12 11.25
12.5 45.5 11.5 12.5 11.5
13 46 12 13 11.625
14 47 13 14 12
15 48 14 15 12.25
Belt Size Guide
Waist Size Inches Belt Size Inches Belt size CM Strap Length Inches Strap Length CM
28 30 76.2 36 91.44
30 32 81.28 38 96.52
32 34 86.36 40 101.60
34 36 91.44 42 106.68
36 38 96.52 44 111.76
38 40 101.6 46 116.84
40 42 106.68 48 121.92
42 44 111.76 50 127.00
Colorway Onyx 3 colorways
Size Ruler What size am I?
Color & Size Arrow up

Dress shoes like sneakers.

While our Gambit Double Monk has a bit more horsepower than your typical dress shoe, it’s a surprisingly smooth ride that anyone can pull off. With its pressure-relieving two buckle construction and sleek silhouette, the striking Gambit somehow feels and performs as fantastic as it looks. The ultimate combo, in our eyes.

Softer. Lighter. Better.

All shoe uppers are made from a full-grain Italian calfskin, specially formulated to maintain shine but require little-to-no break in time.

Like walking on clouds.

We’ve developed a long-wearing memory foam for the entire footbed, tongue and heel collar for all our shoes, providing a resilient cushioning system that hugs your feet every time you take a step.

‘‘Stylish dress shoes made to feel as comfortable as sneakers... by a former Adidas designer’’
‘‘Wolf & Shepherd is pitching men's dress shoes as comfortable enough for long commutes.’’
‘‘All the comfort of a running shoe..and now they have a world record to back it up.’’
‘‘A former adidas designer has reinvented the dress shoe to be as comfortable as sneakers.’’
Customer Reviews
4.8 Based on 107 Reviews
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AL
03/22/2020
Alexander L.
United States United States
Quality Build and Stylish Looks

Haven’t yet run a half marathon in them yet, but have no doubt that I could!

  • Comfort Just Another Dress ShoePretty GoodRidiculously Comfortable
  • Width Feels too narrowFeels just rightFeels too wide
  • Sizing Runs SmallFeels Just RightRuns Large
AL
03/22/2020
Alexander L.
United States United States
Quality Build and Stylish Looks

Haven’t yet run a half marathon in them yet, but have no doubt that I could!

  • Comfort Just Another Dress ShoePretty GoodRidiculously Comfortable
  • Width Feels too narrowFeels just rightFeels too wide
  • Sizing Runs SmallFeels Just RightRuns Large
AL
03/22/2020
Alexander L.
United States United States
Quality Build and Stylish Looks

Haven’t yet run a half marathon in them yet, but have no doubt that I could!

  • Comfort Just Another Dress ShoePretty GoodRidiculously Comfortable
  • Width Feels too narrowFeels just rightFeels too wide
  • Sizing Runs SmallFeels Just RightRuns Large
AL
03/22/2020
Alexander L.
United States United States
Quality Build and Stylish Looks

Haven’t yet run a half marathon in them yet, but have no doubt that I could!

  • Comfort Just Another Dress ShoePretty GoodRidiculously Comfortable
  • Width Feels too narrowFeels just rightFeels too wide
  • Sizing Runs SmallFeels Just RightRuns Large