As a longtime fan of chukka boots, I would like to comment with a concept first, and then specifics.
The chukka is a riding boot, at heart, and so some of the very best chukkas can be found by makers who specialize in boots more than shoes.
If you've won the lottery get a pair of Dehners made for you just as you like at your local riding academy.
If you have won the lottery and married an heiress, get a pair of Riders made for you.
If none of the above are true, look to British makes like Sanders, who still trade a lot in uniform items.
Then look homeward to boot manufacturers. Red Wing has some beautiful chukkas.
Frye does as well, for less money.
The AE chukka costs a bit more, but it is a better shoe than the Frye. It costs more, however, than the Red Wing, which to my mind is a better boot than the AE.
If you would like a chukka that can polish up and go with a blazer and trousers, should you have to travel and want to bring only one pair of shoes that can log miles, handle weather, and still dress up, the Red Wing is my number one vote in terms of quality and price, followed by the Sanders Holborn and AE Malvern (which has a rubber sole--if you like).
I would also look at Alden of Carmel, which has the Alden classic shell chukka in calfskin and with a commando sole (like the Red Wing). The calfskin brings down the price a few hundred dollars from the shell.
Good luck!
