Assuming you're in SF and have a high-paying software job. Find a hair stylist in a mid-range salon who you can actually talk to, show them some pictures of haircuts you like, and let them find something that works. If you find a professional and are OK paying them a bit extra, you'll get good results.
As for "clothes that fit", I have a terrible eye for that, so when I go shopping I just ask a more stylish friend to come with me, or I just ask the shop assistants a lot of questions. Again, they're professionals. They know what works.