It's a challenge for me, but I like it! I sew and make a lot of my own clothes. I also don't mind buying second hand.
I've never been able to find those thrift stores you hear people about where you buy designer stuff for €10. I do like to buy online, I prefer our local alternative to Craigslist. For jeans, I prefer Levi's. I know exactly which fit I need to buy and they last for a long time. I recently bought a pair for €25 that was completely new. The previous owner had bought it a size too small, as 'motivation' to lose weight. This is apparantly a pretty common thing for women to do.
I generally buy shoes new, but like the previous poster I buy good quality shoes and boots and they last me for years. I take them to the cobbler's to have them repaired when they start to wear out. I am currently wearing a pair of cowboy boots that I've owned for 10 years. They had a price tag of €300, but I ended up buying them for about €50. I've had the soles fixed 3 times for about €10 each. I do polish them every now and then like you're supposed to.
I ask a friend to cut my hair, she's good at it. I pay her back by doing stuff for her. I don't dye my hair. There's nothing wrong with the colour I have naturally, I'm not going grey yet (although I'm not planning to dye when I do go grey, I can understand why people do that).
All in all the most important thing is to have very few clothes. A lot less than most women have. I have two pairs of day-to-day shoes, a pair of sandals, two pairs of heels ( I only wear them to parties) a pair of running shoes and a pair of snow boots. I have my work Eastpak, my private Eastpak and two fancy expensive bags that I've had for years and years. I have one spring-and-autumn coat and one winter coat. I don't buy multiples of things unless I really need them - rest assured, I have several pairs of underwear, t-shirts and socks. I don't, however, have an entire drawer of lingerie or socks, but enough to last me about 2 weeks. I only buy items I truly love, which I guess is the opposite of a capsule wardrobe. I hate all this black, grey and beige that I see other people wearing. I buy only what I love and I wear them until they are completely worn out.
As for make-up: I try to wear that as little as possible. I don't wear foundation, but instead a cheap BB-cream. I try to buy natural cosmetics. Only my mascara is expensive, because my eyes burn from other brands, but I don't wear that every day. I go for a natural look.