The shoe conundrum

My winter boots, which have lasted me through several winters now and been reheeled twice, are finally starting to wear out beyond repair. The sole is so thin that I can feel the sidewalk through it, and the lining is worn away to nothing in places. But I continue to cling fiercely to them, determined to make them last out the winter. This isn't just another example of my reflexive unwillingness to discard anything that's, by any stretch of the imagination, "still good" or possible to repair. No, in this case, I'd actually be quite willing, at this point, to spring for a new pair of boots. The problem is that I can't find any.

You see, for me, a pair of boots (or any other shoes) has to meet a fairly rigid set of criteria:

1. First and foremost, they have to fit me comfortably—and my shoe size is 6.5 wide. Many shoes come only in whole sizes, and most don't come in wide widths. And in order to be comfortable, they have to have at least a modicum of arch support (though that could be added, if there's room for an insert) and a flat or low heel. The vast majority of women's boots, even those designed for winter use, seem to have heels too high to walk in, at least any farther than from the elevator to your desk.
2. They have to be vegetarian-friendly. Most shoes, even those that aren't made primarily from leather, have some leather in either the trim or the lining. (I'm willing to wear leather shoes if they're secondhand, on the theory that in that case, my money is going to support the secondhand seller rather than the factory farms that rely on the sale of cowhide to boost their profits. But if finding new shoes in my size is difficult, finding them secondhand is virtually impossible.)
3. They have to be reasonably well-made. That means that, for a pair of winter boots, they have to be thick enough and warm enough to keep out the cold, rain, and snow. They also need to have at least a little bit of traction for walking on slippery sidewalks. Ideally, they should be study enough to last for several seasons (with repairs as needed), but at a minimum, they have to make it through one winter without falling apart.
4. They have to look decent. Not gorgeous, just decent. I don't think I'm terribly picky on this point—all I ask is a simple pair of boots in a dark, neutral color—but these days, that seems to be a taller order than you might think.
5. They have to be reasonably priced. My benchmark used to be around $30 for a pair of boots, but lately I've concluded that $50 is a more reasonable number—yet even that seems to be a hard figure to hit these days. And paying more than $50 for a pair of boots that will only last me one winter just sticks in my craw.

And let me tell you, folks, there ain't a lot at the intersection of that Venn diagram. Back when I was a kid, I used to be able to go to a shoe store, try on shoes until I found a pair I liked, buy them, and take them home. Now, I've pretty much given up hope of ever being able to do that again. Every so often, in a triumph of hope over experience, I'll pop into a shoe store and peruse the racks—but I seldom find even a single pair to try on, and when I do, I usually don't have to do more than slip one of them onto my foot before I hasten to slip it off again.

Unfortunately, this is one area in which the vast shopping mall that is the Internet doesn't offer much help. There's simply no way to know whether a pair of shoes will fit comfortably without trying it on. Most online sellers of shoes have liberal return policies, but they don't cover the cost of shipping—which, because shoes are fairly heavy, can come to $7 or $8 each way. I'm willing—even eager, at this point—to pay more for a good pair of shoes that fits, but not to pay anywhere from $7 to $16 just for the privilege of trying them on.

Over the years, as it's grown harder and harder to find an acceptable pair of boots, I've come to the conclusion that it's necessary to relax at least one of my strict criteria. For instance, the last time I bought  a pair of boots (from Lands' End in 2007), I compromised on the use of leather; the uppers are made chiefly of fabric, but there is a tiny bit of leather in the trim. And I'd be happy to make this same compromise again if I could simply buy a new pair of the same boots from the same manufacturer, but of course, Lands' End no longer makes them. (They currently have exactly three pairs of boots available in wide widths, all made of leather and all priced at $130 or more. I'm willing to compromise on one of my criteria, but not to throw two of them completely out the window.)

More recently, I tried compromising on my fit requirements instead. Back when I was a kid, I sometimes bought shoes that were about half a size too big so that I could "grow into them," so I thought maybe I could make do with a 7 regular instead of a 6.5 wide. So I ordered a pair from ShoeBuy.com, which was offering a deal with free shipping and free returns. I was able to squeeze my foot into it, but it was definitely too tight—and definitely too long, also, so that simply sizing up to an 8 regular was clearly out of the question. So those cozy chukkas are now packed back up, waiting to be dropped into the nearest UPS drop box. (But at least I'm not out of pocket on them.)

At this point, I'm not sure which criterion I need to compromise on next. I could go way out of my price range to buy from one of the specialty vegan-shoe retailers out there, like Pangea or Moo Shoes, but most of them don't carry wide widths, and I'm not about to pay $150 or more for a pair of boots that doesn't even fit properly. So I'm thinking my best bet may be to compromise on quality and give Payless another try. Every pair I've tried on there to date has been flimsy and completely lacking in support, but maybe with a suitable insole...?

I can't believe there are women who actually go shoe shopping for fun.