Jeans
Tshirt
Chucks.
That's pretty much all I need. I never had been nor will I ever be that girl with all the nice accessories, dresses, skirts, blouses, etc. I'm most comfortable in jeans and tees. Lately I'm been trying to dress it up a little bit (e.g. nicer tees instead old tees).
I just don't like shopping so much any more with the extra weight. I sweat this last time I bought clothes, I literally ran in the store, picked the tops I liked in the largest size, paid for them and left...and hoped for the best. So far so good. I rarely try on anything. But jeans I had to because each store is different. Once I find the right size, I'll pick up the rest in that size, different colors.
I prefer to spend my money on other things, my cars, restaurants, home décor, etc.
Oh and for work..? Luckily I only come in a couple of days a week and spend the rest at home. So that means pj's if I don't have anywhere to go. Otherwise when I'm in the office I wear a decent top, black or gray slacks, and tennis shoes or flats, depending on the weather.

And flip flops. All summer, all flip flops. I have various colors for matching, but I usually go with black because they can go with just about anything.