Every spring, I realize I have no comfortable footwear besides my collection of Reef "Sandy" flip flops. I've worn them non-stop from May to October for about seven years now. What they lack in elegance they make up for in comfort since they are nothing but soft fabric ribbons attached to a cushy rubber sole. But last summer I started getting shooting pains between my toes and my Achille's tendons also started to complain. I'd gotten literally thousands of miles out of my Reefs up to that point, but I knew their days were numbered.
I just want simple, low-heeled sandals that aren't ugly and let me to walk many miles every day without blisters. It proved impossible for many years. I can't wear sandals with textured or embossed insoles, or sewn-in labels. So many brands emboss their logo right at the heel, and it's painful. I can't wear stiff leather soles or most styles of uppers. If there's raised stitching or hardware touching my foot, it rubs. If there's elastic at the ankle or across the foot, it bites me. I can't wear "comfort" brands like Merrell, Born, Teva, Clark's, Sofft, Ecco, Naot, Keen, Munro, Rockport, Earth, and so on. I can't wear any thong styles except those Reefs. (I can't even try on Jack Rogers sandals, cute as they are. That perforated daisy on the insole is a torture device, as are the thick thong and stiff sole.) I can't wear slides... although I found one, perfect, woven leather slide back in 2003 by Aerosoles that I lived in. I wore out four pairs over several years (taking them to the shoemaker until they couldn't be revived anymore). I bought every size 7 I could find until they vanished from eBay and the earth. They were the last sandals I loved.
Every spring since then, I've ordered LOTS of sandals, usually in groups of three or four styles at a time. I choose carefully: reading the descriptions, eliminating anything that's really ugly, watching the videos, and scrutinizing the details — knowing I'm still likely to fail. The sandals arrive together in one big box from Zappos or ShoeBuy. I try them on and test them around the house to see how much they hurt, knowing that they will hurt, and then I usually slap on a return label and haul the lot to the UPS store on Newbury Street. Then I order a few more styles and repeat the process multiple times. In the end, I usually keep one pair that I've grudgingly chosen as the best of the lot. Last year it was a closed T-strap by Cobb Hill; the year before I settled for a style by "The Flexx." When I finally get brave and wear them outside, they often start bothering me within a few minutes. I try to break them in, but eventually go back to my flip flops, leaving another pair of sandals gathering dust in my closet. (The Cobb Hills, in tan, were not all that bad, at least for a while. But I've realized they'd look best with a square-dancing outfit and I don't have one. And, fyi, this year's version of that style is made a bit differently and is less comfortable.)
This year, I'm amazed at my luck. I ordered about 15 pairs of shoes and ended up keeping three. It was a Christmas miracle in June. The winners are these "Capricorn" sandals by Naturalizer.
To me, they are vaguely "old lady" but they look much better on — simple and unobtrusive. I've worn them for many miles now, without any problems after the first day, when my little toes complained a bit. There's stitching on the insole, which I feel, but it doesn't hurt. After they proved themselves, I ordered a pair in black. I will probably order two or three more pairs when they go on sale later in the season. They make different styles with the same sole and I may try some of those, too. I've paid between $47 and $59 so far — a small price for the amount of relief they give me and all the miles they'll go.
It's SO wonderful to walk everywhere in sandals that don't hurt and look nicer with clothes than flip flops. I feel very lucky, finally.
I also can't wear cute little Keds sneakers because they attack the back of my ankle. For sneaker-ish situations, I now have these Bernie Mev "Catwalk" flats in denim:
They are a million times better than flip flops when it's raining, for one thing. And they are warmer than flip flops or sandals on chilly days in Maine, too. They are soft and flexible, and kind of artsy-looking on the foot. The only problem is that I had to size down to keep them from slipping off my feet and so they rub a little against my big toe. But it doesn't hurt and I figure they'll stretch there sooner or later, especially if I keep wearing them in the rain.
I haven't worn my third pair of keepers outside yet, and I can't believe you've stuck with me and read this far, so I'll save those for later. Go order a pair of those Naturalizers, which come in lots of widths and colors. They're amazing.