I love square-toe boots. Love the look. Love to wear them 
I really didn’t love the look of the square toe boots, but found a pair highly on sale…and what do you know, I love them.
Then again, getting a good deal can sway me to like just about anything.
Guess it depends on what you are doing in a day, what kind of boots you choose.
I use my Western boots for riding. This means I want semi-round toes, with some height to the tops as leg protection. I WANT leather soles because they ARE slippery to let my foot slide in and out of the stirrups easily. My riding boots MUST have high heels (not fashion high boot heels) as a safety measure to prevent my foot sliding on thru a stirrup. Western boots were developed as a tool for riding, not comparable to work shoes you walk in much of the time.
Square toes can be a touch more difficult to “nose into” the right side stirrup like the pointy or semi-rounded toes are. Other wise I have nothing against square toed boots, just don’t have as “sleek” of a look as the more rounded or pointed boots do while in the saddle. Probably very comfortable for wider feet and doing more walking. My daughter has a couple square toed pairs of boots and likes them quite well, and hers have the high heels for riding in.
I don’t care for crepe-soled boots as a riding boot, don’t think they would help much for getting your foot out of a stirrup fast, or prevent foot going too deeply into the stirrup with those low walking heels. I know they have been around for years, all the big name folks wear them, but seeing the white soles, low heels in a riding situation always strikes me as “wrong” in the safety department. I don’t think ANY of the modern sole material, lugs or modification away from leather, are good for riding boots. Not enough slip and often much wider than soles with stitched leather edges that aid in preventing boot hanging up on sides of the stirrups. How many folks get wider stirrups for their wider boots to use on western saddles or just go riding anyway, with what came with the saddle? Good way to get hung up in your stirrup, even just dismounting!
My daughter also has had the roper boots for just walking and working, says they are very comfortable, likes wearing them often. But she never wears them on a horse because of their low heels. I have her indoctrinated about that! She has also seen some “incidents” with those boots, short heels, while riding at shows and horse gatherings, so she really understands my point of view much better these days.
Western boots are a good example of a working tool, modified to use in places other than it’s original use. Some of the changes work, others are “fashionable” but not really practical. Western boots with high heels were never meant to be walking shoes, snow shoes, or to spend all day wearing as you do chores on the place. So wearing those modified western boots for the original purpose of riding, may be a BAD idea! You could get hurt if you need to bail off or get thrown and your feet don’t come free with sticky soles!
All Western boots are not even close to similar, beyond being in the “boot category” of footwear.
I think the square toes are on the way out, at least judging by what’s on super sale at TSC right now. And what’s not. I don’t like square-toes to ride in.
I can’t even wear my paddock boots to ride my half-lease horse. He is adorable in all other ways, but he sees no point in lingering at the mounting block. Once you’re up, human, we’re off, is his motto. I like my round-toe ropers because it’s easier to pick up the off-side stirrup on the fly. 
I really love the pointy-toe Justins TSC has for sale right now. But they are too pretty to ride in.
I like round toes for riding but much prefer the square toes if I’m going to be walking. I think my toes have flattened out from being stepped on one too many times.
As a side note, do the heel savers really work to keep heels from wearing off? I saw them for high heels but wonder if they work for either heels or boots.
