Chukka boots or Desert Boots are rather popular today, and there are many manufacturers of casual chukka boots and also bespoke versions of it. Considering the casual nature of the Chukka boot, I would never combine a crepe sole Chukka boot with dress pants or a suit.
At the same time, an elegant Chukka boot can be paired like a suede shoe, and looks great with dress pants and suits. For example, I have an elegant pair of St. Crispin Chukka boots in mid brown suede leather that goes very with almost anything I wear.
The possibilities of incorporating them into one’s wardrobe are endless. Dress Chukka boots with thin leather soles on an elegant last in brown can be paired with a navy or mid-gray suits and a range of other colors and patterns.

$39.59

  • Sneaker-inspired chukka boot featuring lace-up closure and rear pull loop
  • Wraparound midsole
  • Ortholite PU footbed made from 5 percent recycled rubber provides all-day cushioning and support
  • Sensor flex technology delivers underfoot support, independent suspension and greater flexibility for the ultimate smooth ride over any terrain

$88.76

  • Breathable upper
  • Flexible sole
  • Non-marking outsole
  • Cushioned
  • Ortholite footbed

$103.66

  • Sole features geo-detailed rubber forepart, leather waist with branding emboss and colored heel top piece
  • Richly colored leather lining alongside sock with repeat print pattern and Ted Baker branding stamp
  • Two colored laces are offered

$232.99

  • leather
  • solid
  • manmade-sole
  • closed-toe
  • lace-up

$60.99

  • Extremely lightweight
  • Flexible sole
  • Non-marking outsole
  • Breathable leather upper
  • Ortholite memory foam

  • Back pull tab design for easy to wear on/off
  • Flexible Rubber Out-sole with the Slip Resistant fucntion while in walking
  • The nylon laces allow me to have looser laces across the top of my lower foot, and tighter up above where the ankle is. This is extremely comfortable.
  • Genuine Leather Upper allow me keeps foot dry and clean, Breathable and comfortable
  • The design is very modern and would look nice with a dress shirt for almost any occasion, whether formal or just casual.

$30.71

  • Square-toe chukka boot in glossy leather featuring lace-up vamp and pinked brogue trim
  • Stacked heel

$73.57

  • 4-eye boot
  • Durable grizzly (type of bovine leather)
  • Good abrasion resistance
  • Slip resistance
  • Air-cushioned sole with side-wall stitch

$50.21

  • Ankle-high chukka boot with suede upper featuring four-eye lacing system and moc-toe stitching
  • Contrast leather heel counter

$45.68

  • Multi colored micro woven fabric lining.
  • Moisture wicking micro mesh fabric covered bounce eva footbed chassis with shock absorbing heel strike pad and forefoot energy return pad provided all day comfort.
  • Bounce two density rubber outsole with shredded jute inlay.
  • Worry-free suede: protective coating resists scuffs, stains and water to keep shoes looking new with no hassle.
  • Bounce: triple density footbed provides a shock absorbing heel strike and energy return forefoot. dual density outsole releases energy with each step by absorbing and redistributing shock.

-2%
$64.19 $62.99

  • Sneaker-inspired chukka boot featuring lace-up closure with padded top collar
  • Ortholite pu footbed made from 5% recycled rubber provides all-day cushioning and support
  • Unique L7 lug design features multi-directional leading edges with beveled lug sidewalls that allow for self-cleaning and superior traction on a variety of surfaces

$64.99

  • Lace-up boot featuring contrast collar and lugged outsole
  • Comfort system designed to provide lightweight shock absorption.
  • Hydro-shield construction offers waterproof leather, a seam sealed, waterproof insole, and a gusseted tongue to help keep feet dry
  • Sponge ethylene vinyl acetate footbed conforms to the shape of the foot for a personalized fit

$31.65

  • Genuine leather upper
  • Soft twill lining
  • Memory foam footbed cushioning
  • Flexible outsole

$35.99

  • All Men Made Material
  • 5 eyed lace up and wingtip toe
  • Wooden sole with slip resistant rubber pad on the heel
  • Lightly padded insole
  • Fabric lining

$68.00

  • Leather chukka boot with blind-eyelet lacing and stacked block heel
  • Single-stitched welt
  • Pull-on loop at opening

$47.99

  • Outsole: TR provides a durable grip on a variety of surfaces
  • Upper material: leathers and suedes
  • Footbed: eva cushioning conforms to the shape of the foot for a personalized fit; eva heel cup provides support, a secure fit and cushioning.
  • Lining: soft knitted fabric that feels great against the foot