There's been some discussion on wearing Alden boots in Texas. I know San Antonio and Austin don't get as cold as Dallas in the winter. Houston is almost always pretty warm, and really humid! No doubt I'm not going to wear boots, including cowboy boots on a 100 degree day. However anytime its below 90 degrees I do wear boots. I'm a native Texan and i have worn cowboy boots in over 100 degree weather when horseback riding. Footwear in general has evolved to be more of a fashion statement rather than being used as a tool for what they were created to do. I've done a lot of hiking in America too...in the summer and I always wear my boots designed for hiking. Since most Alden boots only go slightly above the ankle I honestly see little difference in wearing an Alden shoe or boot when looking at outdoor temperature, the part of the foot that sweats is covered the same. No question a cowboy that covers the calf is warmer, but I always wear a boot sock that covers my calf when wearing cowboy boots and that helps. My main point is that most quality shoe manufacturers designed their product to meet a need. In particular the Indy boot was, and still is a work boot. The use of shell cordovan was and still is primarily used for its durability.
I do own multiple pairs of Alden chukka's, and cigar to me is one of the most versatile for business casual to casual. I do have cigar NST and LWB I like both of them too. A lot of your decision revolves around the color of the cigar you get. My Chukka's and NST are the older, lighter, more olive colored. The LWB are the darker newer cigar. I say 1 of each please!
By the way I don't think I've ever welcomed you to Texas...Hope you enjoy the Lone Star State and good BBQ and Mexican food!