I'm a fan of supporting local shops--not just because it seems to be the trendy economically-friendly thing to do, but because I like finding places that are unique.
Gwenneth's Shoe Repair is one of these places. I've taken several items to them over the years--boots to get stretched, a leather bag to be cleaned, several pairs of shoes to be repaired--and I've always been very pleased with their work.
It's a fun store to go into--they have all sorts of leather goods that they've either made or refurbished--and the staff is always personable, knowledgeable, and friendly. They'll punch holes in shoe straps for free. They found the perfect shade of polish for Colin's vintage cowboy boots. The people in front know their stuff, and if they don't, they'll pull the repair guys up front to talk to you. When I brought my $650 Rebecca Minkoff bag in (that was a contest win, by the way, not something I could ever afford), covered in grime because I'd carried everywhere for months, the guy who cleaned it cleaned it three times because he wasn't satisfied with how it came out at first. They truly love and take pride in their work, and I like supporting people with that sort of integrity.
I don't like walking into repair shops cold--I'm always afraid I'll get ripped off--but I trust these guys. They do make you pay up front, but the prices seem quite sane, and I like that better than handing it over and finding out later it's going to be more than you bargained for (a la the car mechanic). I hope that my recommendation is enough that you're willing to try them out, too, even if it's a bit of a drive for you. It's worth going to someone as good as they are.
They're at Rudasill and Oracle, on the Northeast corner, behind Putney's.