alright, no maxi dresses for you. they were in last year, skinny people hated them, medium people hated them, chubby people hated them. i, for am glad they're gone.
staples, how much can you spend? i don't shop at target or old navy as those clothes don't last long. you want to buy things that are more timeless meaning they don't go out of style next season.
if you're starting from zero, you can't shell out so much money to update your wardrobe, do a few things a month, set up an amount for yourself, just yourself each month. i'd rather spend a little more and know that that thing will last me a few summers than buy a thing here that i know will be ruined by the washer/dryer, get faded or shorten in length.
so, the stores i get my stuff are: abercrombie for jeans (they have nice stretch to it, they're reasonable priced, and they make me look like i have a behind. good enough for me. about 50 bucks), you need one pair of jeans, get a dark wash with a bit (not much) faded over your legs. then short sleeve shirts, i get mine from banana republic and jcrew. just a few, that i can dress up or dress down. in reality i never have to dress up as i am not going anywhere, but let's say 2-3 from these two stores, go nice colors, no blacks no dark browns. i also get my shorts from these two stores, get two colors, one light khakki and one green and you can combine these with all the tshirts you've gotten, same thing for capri pants 1-2 pairs (different colors). you would need 1-2 skirts, nothing stretchy, uncomfortable or shiny, cotton is fine, with a bit of stretch in is if you need it. same thing, you can wear the tshirts with these skirts, get 1-2 cardigans. now that i typed i get all my clothes mainly from br and jcrew. just their material and style is nice, not complicated, not trashy but nothing over the top.
i don't do leggings, didn't do them in 80s not planning on wearing them now.
you'll need 1-2 pairs of flip flops/sandals. i love stuart weitzman. i use 6pm.com or smartbargains when i am looking for a deal, even though i have shelled money for this brand at the higher end dept. stores like bloomingdales. stuart weitzman stuff is awesome, fit like a glove and very unique in style.
winter time: oh i am not going to depress myself thinking about winter. but will say this: i love laundry by shelli segal winter coats. they're not bulky, they feel so comfortable, beautiful in style and if you wait until dec. they go on sale. i get these at macys.
EDIT: i don't have a set amount for myself to spend each month. i get as i need things. i put aside money for myself (cash) each month and once i have enough in my onion i go and get my stuff. in meantime i gather my coupons, and email fwds with coupons. i don't think i pay full price for anything. there is always times in a month when stores run sales or send coupons.