Clothing advice

I go to re-sale shops. You can actually find nice pieces in nicer stores. I think you should get 2 pairs of jeans, 2 pairs of dress pants (black and tan maybe), a black pencil skirt, and no less than 7 work appropriate tops if you are looking for 12 items.

Glamour Magazine does a spread every month of a month's worth of outfits using like, 4-5 pieces. Maybe look into that? They wear at least one of the items every day, but they do supplement with other pieces.

a couple of thoughts....looking at re-sale shops is always a great option....you can ususally find like new clothing at a much cheaper cost than new.
or
if you want to buy new...go for the basics for now...black / grey pants, neutral color jacket or sweater (which ever you prefer), black / grey skirt. then get some tops to make them pop! with the bottoms being basic colors - you can wear them year round (if you get a 3-4 season material), and then you can splurge a bit with the tops so you will have a variety and not get bored

I wouldn't buy top of the line clothing until you reach your ultimate goal...I understand you will want good quality, but top of the line may not be necessary for this interim period.

clothing could be a way of celebrating each levels of your goals!
Good Luck - with clothing and the lifestyle change!!!

p.s. another thought...when these don't fit anymore, pass them on to someone who could use them or sell them to buy new smaller clothes!!

I agree with the idea of focusing on basics. When I lost weight a few years ago, I got some basic pants in black, grey and khaki and a skirt or two. Most of my tops were fine, so I didn't need to replace those. Stores like Ross or Marshalls are another good option, because they often have nice things on deep discount.

Firstly, look at your colour scheme. What jewellery, shoes and scarves etc do you have - that might dictate the colour of items.

I base my work wardrobe round a touser suit - plain black pants and jacket would do for this, though it can look a bit sombre. Particularly in the summer, a beige is nice and neutral.
Using your existing shoes/ scarves etc as a guide, decide on an accent colour (turquoise, coral, lime green, say).
Pick a couple of tops that work with the suit, using your accent colours, and a dress that will work with the jacket. Choose a dress style than can easily be cinched in with a belt as you go down a size or 2.
I also like cardigans as a jacket alternative - loose waterfall front ones will last you through several dress size changes better than fitted ones.
Aim for items that will go with each other - the cardi or the jacket both work with the dress, cardi, trousers and a top for less formal days.

And I love hunting round charity shops, or discount stores like TKMaxx!