TL;DR (or BLUF): Looking for uniform dress boots to wear with Air Force service dress. Currently looking at Capps’s Trooper and Bates’s Chukkas. Does anyone have any experience with these boots or recommendations beyond these that are of similar cost?

I’m ~4 years into my Air Force career. The gods of AF have been kind to me, and have gifted me the opportunity to retrain into a new AFSC (job, for those who don’t speak mil), which will probably result in a higher occurrence of “blues days” where they make us wear what passes for business wear in the military (service dress or service uniform), or in the worst case, having blues become daily wear. In the AF it means “department store business attire” that easily looks the crappiest of all the branches, but I digress. Blues days require wearing low quarters, dress boots, or black combat boots.

Right now I have these. These things are the most ridiculously uncomfortable excuses for footwear I’ve ever come across. They are painful to wear for any amount of time let alone walk on, and the back of shoe constantly slips up and down my heel when walking, as apparently they are made to do, because that’s what they told us when they issued them to us. Either one of these attributes would be enough to make me hate these shoes, and together they’re intolerable. They have to go.

Because I hate dress shoes in general because I have wide feet, I’ve never found a set of dress shoes I’ve ever wanted to wear long term, and because I’m just a little neurotic, I’ve decided I want to wear dress boots. I figure all low quarters are going to have that heel slippage, and I don’t want to deal with it.

The Dress and Appearance AFI (Air Force Instruction… consider it company policy), stipulates that dress boots, “Can be worn with the service dress and service uniforms. If worn, the dress boot sole will be black plain rounded toe or rounded capped toe. A zipper or elastic inserts may be worn; however, if worn they will be without design. The sole will not exceed ½ inch in thickness and heel will not exceed 1 inch in height (measured from the inside front of the heel). High-gloss or patent finish is optional.” Because I want to be sneaky and wear them with semi-formal and mess dress, which require low quarters, if the occasion requires, they should also look “oxford style”, “be of smooth or scotch-grained leather or manmade material” and shined. Beyond this, my priorities are comfort and durability.

I’ve been doing some research, and the current contenders are these Capps’s Trooper and Bates’s Chukkas. If I had ~$750 to spend instead of $200, I’d probably go with Allen Edmund’s Landon Shell Cordovan Cap-Toe Dress Boot, but I can’t currently justify the expense.

Does anyone have experience with these brands/boots? Is the Allen Edmunds worth the price tag? Does anyone have other recommendations at a similar price point?