They can be expensive, but your feet WILL thank you. Well-made leather boots will hold up for a long while, provided you care for them (saddle soap with mink oil in it will do wonders). You might have to forgo a single saber with sound to get them, I will admit, but...
One of the best places to find the style you might like would be a Rennaissance Faire in your area. Most of the shops that sell them have cards, and if you explain that you're shopping they should be able to fit you in-store. Then, use the web address on the card to check out the virtual shop - a lot of folks at Faires have to charge higher amounts for rent of the storefront.
My wife has a pair by one manufacturer, the name and site of which I'll PM should folks wish, that will re-sole the shoes for life that she inherited from a friend who bought boots WAY too small (silly, but he's a sucker for an enthusiastic, persistent sale). It cost a bit to do - but she went into their storefront at a local Faire, and even though her boots were of a style that hadn't been MADE in ten years, they recognized the boot and said they could fix it, which is a pretty awesome thing in my book. The boots ARE pricey, but so long as you take care of the boots, the manufacturer will replace almost anything that you do to them, and cover EVERYTHING that could result from workmanship defects.
I got mine from a different manufacturer, as mine were more basic and our own purchase. But, I dolled them up with some extra strap work and a leather covering for the top of the foot that I think looks pretty good.
I do Renaissance Faires myself and I have to agree with ed_ification. The boots available at Faires range from a plethora of different styles and fittings. However, on that note I would very much recommend purchasing from surplus products during the off-season (i.e. now until march which is the beginning of Faire season) on amazon. You will save a considerable amount of cash then from purchasing it up-front.
If not, well then taking a trip to your local Faire is always fun, however, in many ways I prefer the comment below to not only save on some cash, but to allow you to customize your boots for many different occasions.
I have been giving this boot aspect some thought.
For those who played baseball, think about the leggings/socks
The red ones...picture them in light weight upholstery material, a leather-ish product...$10-20 tops.
Match a pair of shoes to the leather-ish product or vice versa to the leggings.
Simple to put together and inexpensive.
On a different note, Jedi Relmeob has the right idea in making your own boots, or rather graves / legging / boot slops in that it is a FAR more economical and cost effective alternative as opposed to purchasing full calf-high boots.
I also argue it allows you to keep your options open.
Have some military boots but don't want your strings to show?
Put the leggings over them.
Have some regular brown or black dress shoes from a thrift-store but are just not very Jedi-like?
Put some leggings over them.
Using those socks as an example, you can construct your own fitting of leggings from leather to not only fit onto a number of different types of shoes preferably leather ones, but it also gives you the feeling that you're wearing a nice pair of boots only there's better breathing room and it actually feels like you have armor on.
I'd do it myself to show an example and save myself some cash not to mention accomplish a long-awaited dream of mine, except that I have limited knowledge on sewing leather together and my ability to rivet leather is sub-par.
