It took me 2 years to purchase a pair of capris. I (and my momma ass) are boycotting the stretchy leggings that have reared their ugly heads for a second time in my life. The first time, I was 10 - and rocked the HELL out of them.
I'm all about comfort and function. Pants that are too tight or shoes that squeeze my toes make me all grinchy.
On a typical day, I am dressed in standard jeans and t-shirt - although I've recently updated to a collection of comfy-yet-mature versions of my college tees. I can get dressed up, and if I do - I go all out. Especially when it comes to a professional situation. Luckily, my current job requires that I dress to the nines only a handful of times a year. I can't be expected to iron all the time...
I am all about the sensible shoe. I can wear heels, but they are the chunky late-1990s style. I'm clumsy and fall if the shoes don't have a rubber soul or the heels are too pointy. I prefer boots when I'm dressed up - for several reasons... First, I can wear socks that protect and cushion my feet. Second, they hold my feet better and provide better support. Third, they cover an ankle tattoo that I prefer not to be exposed in professional situations. I prefer to wear hiking boots. I have spent more on hiking boots than on any other type of shoe...with one pair at $190. That is a LOT of money for me to drop on a pair of shoes - but they were worn about 300 days a year. Well worth the durability and support they provided.
My favorite go-to summer shoes are a pair of Teva's that I purchased for a very important day.