oh Mander, what a great thread topic! and Thank You to all for great contributions!
i'm all over Team Low Budget and Ultra Picky (on aesthetic, practical, comfort & health criteria) - i can completely empathize! i take a few approaches to this dilemma (which i'm generally experiencing at any moment).
i may see if there is a way i can squeak out some more money somehow - cutting back on treats, telling family i'm very much in favor of cold, hard, cash for upcoming holidays, etc. this applies if more money will enable me to get what i want.
when i'm truly stuck and can't find what i really wanted even if $$$ was no object (the most common situation), then i re-evaluate. i try to strip down my concept to the absolute basics. so instead of 'sandal' i would maybe put 'lightweight, cool to wear' on my criteria list. this opens up the possibilities to include ballet-style flats, oxfords, mary janes, and so on. maybe a delicate mary jane with canvas uppers would fill the bill? i don't know, that's just an example, but the idea is to think about the function the item will fill in order to expand your ideas about what in particular could fill that function. for me, this approach generally helps me find something i really like that will work.
it's always important to 'know thyself'. if i was in your situation and didn't have ANY shoes that would work AT ALL, i personally would choose comfort over 'cute'. no matter how cute a shoe is, if it's giving me blisters or whatever i won't wear them. i personally would also choose a kind of boring, comfy shoe over something 'cute' - i'd rather wear a shoe that blends in with the rest of my look. i can up the style quotient in other areas of my outfit, but nothing will compensate for a look of misery on my face due to foot pain! but the equation will shake out differently for everyone, so it's important to know your own priorities to avoid wasting money and time.
i also have learned how to fiddle with things to make them work for me. i sew, which is worthwhile, so i do a lot of alterations - even on tees and undies! i add full insoles, half insoles, moleskin, new laces, etc. to shoes. clothing and leather can be dyed different colors. buttons can be changed out, etc. how you wear items is important to consider as well - Angie's backward dress is a classic example. a belt can make all the difference. with shoes, with 'hikers' i'll just get a pair that reflects my general wardrobe palette and let the focus of the look fall elsewhere. i don't wear 'hikers' in an outfit where the shoes are the main focus of the look.
i am very lucky in that i have a somewhat unique style, and as a result some of my very generous friends and family will give me items they think i'd like from time to time. they will also let me know when they see something that screams 'me' to them. WHATEVER they give or point me to , i thank them profusely!!!! first of all, how sweet that a person thinks of you and takes that time for you!!! also, i've been given some truly awesome pieces from people, and there is No Way i want to discourage anyone from thinking of me in future!
i'll third Clark's artisan and indigo lines for very well made, comfy, non-ortho looking shoes. try outlet stores, e-bay, and very persistent online shopping for better prices. my husband gets really good deals, and i think it's because he'll spend an hour going over 20pages of google search results & look into all those online coupon codes. it's kinda fanatical, but if you have more time than $$ it's an option.
hope this helps! good luck to you, and thank you and to everyone else for a great thread topic and great ideas!!!! steph