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I have gotten two pair of true boots, one an ostrich pair of Luchessi ropers, in my regular dress shoe size. One of the smoothest, bendable shoe leathers I have ever put on my feet. Another pair of roperrs, more like a work boot, Double H with rubber soles. Workhorse, shit kickers and I feel bad to the bone in them.

Not counting the LL BEan 6 inch rain boot I got.

Now, pairs three and four: A pair of Frye side zip boots and a pair of Frye suede Chelseas. Like them better than Chukkas, both pair

I said all that to say that I truly feel my feet feel better in these fourt pair of shoes, more so than my next favorite pair, Allen Edmonds Park Avenue. Now, other than the Beans and the Double H. just regular foot bed. The Beans and Double H have a molded, padded insole. Others do not. For some reason,here is my theory why they feel better. Like a loafer or dress shoe, the heel is above the arch a bit. Takes pressure off the arch, and puts it on the meat of the heel and the balls of the feet. Thus my arch does not get tired. This make sense?

I never really wore boots, maybe chukkas or hikers here and there, but no, I myself prefer the boots when i don't have to wear dress shoes with a suit.

I have not yet tried on or gotten boots that have like 8 eyelets or come up higher than the Western boots, but I can see why some men wear boots with dress shoes
 

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These are the Lucchese's that grace my feet today. They quite literally feel as if Lucchese craftsmen built them right on my feet! Just can't ask for much more than that. It sounds like you are going to enjoy your boots just as much as I have and continue to enjoy mine! ;)

Brown Durango boot Human leg Leather Fashion accessory
 

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I totally get the arch thing. I have high arches. Several years ago I bought a pair of Alico Tahoe hiking boots in my usual size, but they were huge on me in volume.

So I put in the leather insoles from a pair of Footprints by Birkenstock-- very firm and high arched, similar to Birk footbeds. And the boots have felt great ever since.
 
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