well I'll be fun and pick the option of dressing nice and being in pain lol. but I do use inserts in my heels so it doesn't hurt. I can wear heals for at least 4 hours and then it starts hurting and then I'll switch to something else. I love dressing up, especially in cute halter dresses or any skirt. summer is a great time to wear dresses/skirts. in winter I'm mostly bundled up in snow board gear lol
I like to dress up and wear heels but if they start hurting, it's part of looking good. Nothing's easy but sometimes I just feel like wearing jeans and a tshirt and that doesn't hurt at all. Depends in the mood, but If I had to pick I'd pick option one.
A lot of it depends on the situation. I tend to be a jeans and t-shirt kind of girl most of the time, but I dress up when its needed, and sometimes just because I feel like dressing nicely. But I've found clothes matter less than HOW you wear them-sometimes it is definitely obvious I am uncomfortable when dressed up, and I get less "good" attention then than when I'm comfortable in my t-shirt.
As a matter of fact, most guys tend to hit on me when I'm being casual.