What is a Chukka? Easily put- it's a boot. Why all the fuss though? Because this boot is a great addition to the fashionable males wardrobe for dressing up or dressing down. Its comfort and style can replace the dreaded uncomfortable dress shoes that most of us dislike.
How is a chukka boot different from a normal boot? It isn't really. In general, the chukka boot is lower ankle high and only a few lace holes, think of it as the dress shoe and boot hybrid.
Some chukkas are pure casual, and others can easily replace the dress shoe. Leather sole is typically more dressy, rubber sole more casual (this applies with dress shoes as well).
Now when someone says "chukka" you will know what they are referring to. Just make sure that you wear it appropriately though.
If you want to wear it with a suit, no doubt the sole has to be leather. With chukkas, they typically are built on a very forgiving last, resulting in a comfortable wearing shoe.
Below are some links to chukkas that are affordable and dressy (Zappos). Note- I have also been impressed with the shoes you can find at DSW every now and then. The Bloomington Indiana store has had some great Cole Haans pass through, among other brands- and I'm sure the Bloomington store isn't the most fashionable DSW out there!