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For Out on the Town Men's dress boots it is hard to beat a good Italian pair, the style is timeless and they are usually comfortable on the feet..
@HNSB I have that exact pair of Ariat's I bought them in a pinch as I needed a pair of Black Smooth leather boots I think mine are B toes, one of the most comfortable pair I have ever owned, second only to a pair of Dan Post Elk Skins that I bought about 35 years ago
Honestly my all time favorite Cowboy boots over the years were a pair of Nacona Roughouts that I bought in Glenwood Springs Colorado near 20 years ago the heelback finally broke or would still have them :)
I remember a pair of Black Tony Lama Lizards that were great boots too :p
I hardly ever wear boots, I have sweaty feet. I got a pair in Texas in the eighties featuring a special welt "..that keeps your feet dry when a cow pisses on your boot" as the man in the shop explained to me.
I don't wear Cowboy boots, but I quite like a squared toe version I've seen on a few boots very nice looking, but I will say I've always had a weakness when it comes to shoes or boots, and I've got to say the British make the finest handmade boots and shoes in the world, with makers such as Crockett & Jones, Trickers, Grenson, Loake, I'll leave you with a few photo's of part of my collection. PS If I were going to buy a pair of American Cowboy boots, I think these are the make and style I would be looking at. Lucchese Men's Chocolate Mad Dog Goat Cowboy Boots
Jamie.
Alfred Sargent Chelsea boots.
http://i713.photobucket.com/albums/w.../Wales/006.jpg
Grenson Brogues in Champagne Cognac.
http://i713.photobucket.com/albums/w.../Wales/005.jpg
English Benchmade Brogues.
http://i713.photobucket.com/albums/w.../Wales/007.jpg
Handmade Italian Chukka boots.
http://i713.photobucket.com/albums/w.../Wales/004.jpg