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I guess it's all preference as to what you wear, but i can't touch the ground very well on my bike... (i'll be doing some more lowering to feel comfortable) but i wear wedge sneakers (they usually are high top to cover some of the ankle) i can't find anything in motor gear that gives any height at all. i'm 5'2, so i feel your struggle.

I have 2 pairs of nike wedge sneaks that have done the trick for the past few seasons. Comfy for riding, easy shifting in my opinion, just that if you stop & walk around for a while, you might want to pack something more comfortable (i always bring flip flops on a sunny day stop).
 
I'm wearing these boots from Forma for all my casual riding. It's certainly more of an everyday boot, but at this price provides a bit of protection and grip while still looking really stylish walking around town. It takes some getting used to shifting with a heel at first, but it's second-nature to me now.

They do help me flat-foot, but I am taller than 5'4. I've also looked at the Joe Rocket Heartbreaker boots and they seem like the best option I've seen to really add some height.
 
I know this thread is pretty much dead and the original poster is probably no longer active but I had to chime in here. I may have mentioned that I wore Doc Martens for street riding for a long time. I still stand by the fact that Docs aren't a half bad option for casual riding, depending on the style of boots you get. You can easily lace them loose enough to where you can get some ankle protection in there as well. However, for what you would pay for a brand new pair of legit Docs, you might as well buy some proper riding boots.

As a chick, I like my shoes. So I tend to have a few pairs for all purposes and I am still very much loyal to my Docs (something about that rebellious punk rocker metal chick just won't die in me :p). So last year I picked up a pair of these:



They are the Doc Martens Caitlyn (sp?) boot. I didn't intend to use these for riding because... well just look at these fuckers?! They are pretty impractical for riding in. Hahahaha the platform alone measures about an inch and a half tall at the toe, and over 3 inches at the heel. But if you're looking for a height boost, you're definitely gonna get it.

I don't really have issues with my height when riding anymore but just for shits I wanted to wear these to work with a particular pair of jeans on a Friday. So I gave it a go. I won't lie, moving around the gear shift requires a little conscious effort to get a feel for the clearance but it is entirely possible (although, now that I think about it, I have raised rear sets so this may actually be a problem for someone with a stock setup).

I don't ride in these boots often when I am on the bike, and when I do it is basically some around town stuff with maybe a little long-way-home jaunt at the end. But they do pretty well. Beware though: these boots are a little heavy. The soles are your typical Doc Marten soles that are slip resistant (and yes, they definitely are) with cement construction so they weight about a pound to a pound and a half each. They may not be your style but if they are, they aren't a bad option.

Although, like I said: for what I paid for mine, you can easily buy a mid-range pair of motorcycle boots, but you probably won't get the boost you're looking for.
 
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