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.

$22.27

  • Lace up
  • Flexible sole
  • Non-marking outsole
  • Light weight

$26.95

  • Lace up chukka with soft enzyme washed canvas upper
  • Yoga mat drop in comfort with custom printed canvas cover featuring an antimicrobial additive designed to reduce odor causing bacteria
  • Ultra flexible sanuk rubber cupsole

$39.16

  • Doc martens lightweight boots
  • Durable canvas upper
  • Good abrasion resistance
  • Slip resistance
  • Branded pull tabs

$82.51

  • Cement Construction
  • Rich Nubuck and Full Grain Leather Upper
  • Leather/Soft Textured Print Lining
  • Leather Lined Footbed
  • Sebago® Energy Return Heel Pad

-61%
$69.99 $26.99

  • Suede Upper, Nylex Lining, TPR Outsole
  • Lace Up Front Closure With Blind Eyelets For Personal Fit
  • Shaft Height Measures Approximately 4" From Heel
  • Boot Opening Measures Approximately 13" Around
  • Wedge Heel Height Measures Approximately 2 1/4"

  • Crafted with seam sealed waterproof full grain leather
  • Rebound technology in the outsole provides long lasting comfort
  • Dura fresh bio-technology lining fights odors
  • Slip-resistant rubber outsole
  • Soft leather footbed

$59.99

  • Distressed waxy suede upper
  • Cotton cnavas lining
  • Comfort footbed with woolrich wool
  • Rubber outsole for durability

$74.99

  • Full grain leather upper
  • Retention foam footbed
  • ADIPRENE & ADIPRENE + by Adidas
  • TPU midsole
  • Rubber outsole

$73.15

  • Air-cushioned, synthetic sole
  • 6-eye boot
  • Slip resistant
  • Classic doc dna

$64.99

  • Upper made with premium leather from an LWG Silver-rated tannery
  • OrthoLite® footbed
  • Rubber outsole
  • 1cm internal wedge
  • Imported

$52.99

  • Full Grain Leather upper for a soft supple feel
  • Latex Footbead for extra comfort
  • Microfiber lining. Shaft height: 3.75 Inch
  • Rubber outsole for durability
  • Heel measures 1 inch

Browse Wishlist
$45.45

  • 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

$48.35

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

$103.93

  • 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

$279.42

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

$89.77

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