The chukka boot, like the desert boot, is versatile. It's a boot, which gives it a bit more of a casual look, but it's also a plain toe shoe. Having versatile footwear, and clothes for that matter, can make a relatively small and inexpensinsive wardrobe go a long way. I own a pair of black chukkas from Johnston & Murphy that I've had for about 5 years now, but I would go for either black or burgundy as shown below.
All pictures from Leather Soul