I assume I'm not the only one that struggles to find a nice dress chukka. Either it's too clunky, to big of a sole, wrong stitching, or just not the sleek shape it needs to be. The right chukka boot can look just as good a dress shoe and is much easier to dress down with jeans. Here is a small list of the ones I give a thumbs up to that aren't overly pricey.
The "Castellano" and "Jet" are two of my favorites. It's incredibly comfortable, lightweight, and wears really well. At $135- it's hard to beat. Florsheim is quickly becoming one of my favorite shoe brands on the market.
2. Cole Haan
Like Florsheim, Cole Haan is killin it with the value. It's a well made shoe at an affordable price. The "Cambridge" is a great chukka to add to the mix- unfortunately, they just stopped making it. You can however find a ton of them on Zappos or Amazon. It will cost you around $250.
3. Aston Grey
The "Rancho" is a simple design, keeping the roots of a casual chukka. This boot would look great with sport coats and of course denim. At $109...it is almost hard to pass up.
4. John W. Nordstrom
Haven't ever worn these, but as Nordstrom's house brand they usually deliver a nice product. And if you don't like them they have the best return policy I have ever heard of. $195
5. Allen Edmonds
The "Dundee 2.0" is the most expensive chukka on the list, but it definitely holds its value the longest. Allen Edmonds are typically one of the most comfortable shoes out there (once you break them in). $385
6. Suit Supply
This suede pair is comfortable and sleek, it is a hair pricey, but- finding a dressy pair of suede chukkas are not easy. This would be a great pair to add for the fall season. $249
6. Massimo Matteo
Keep an eye on Zappos for this brand. I have two pairs of Chukkas and they are incredibly inexpensive with great comfort and design. This pair is up for $169.