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I need to work on this- she currently has lots of tips and bottoms that don't match...

I don't and just buy when I notice her outgrowing stuff.

We are doing uniforms this year, so it was easier in terms of what items I could get.

I did 6 pairs of pants, 4 pairs shorts, 6 shirts (long sleeve), 4 shirts (short sleeved), 1 fleece vest, 1 zip up sweatshirt. I will likely buy more fleece vests. My goal is to not have to do laundry during the week.

It helps that I know what my son will NOT wear (button down shirts, jeans) because now I don't buy them.

I do some very general planning just so I can make sure to buy enough clothes for the season and take full advantage of coupons. Usually I count what we've got for the current season and depending on whether that seems like a good amount or like we're struggling to get laundry done in time, I'll go with that number or adjust it.

Since DS is newly potty trained we need to keep a lot of clean bottoms on hand. So I'll probably go with:

10 long sleeve shirts
1-2 sweatshirts
15 pairs of pants

I'm aiming to make the bottoms as neutral as possible so that they can mix and match with his tops, because DH has taken over dressing him and some of the outfits he chooses kind of make my eyes bleed, lol. So I'll do jeans, navy, and gray pants. I love to get pants/shorts from Old Navy. I'll do some tops there too, and I also like Gymboree stuff for him.

We will also have a new baby girl and I know we'll need some fall weather clothes in 0-3 and 3-6 but I don't really have a strategy for her yet. I think I'll get the most bang for my buck at Carters, which I don't like for DS. So that means 3 different children's stores to go to, which is less than ideal. But I'll be on maternity leave, so maybe I'll enjoy having lots of shopping to do.

The last two seasons I've done capsules for my big girl.
I spent time building a interchangeable wardrobe so all typos matched all bottoms, matched all shoes. It has worked out so well.
In previous years I just bought whatever I like but then had a ton of stuff that went with nothing else out clashed terribly with her shoes.

@Mrs D: I am not the best person to answer this since I admittedly go overboard (we are only having one child so ... I give myself permission ). I do plan, though. I know what DS has in his closet and I know he doesn't need more rompers for instance but he does need more long pants. So I am on the hunt for those! Side note: I can't stand that all little boy pants are navy or grey!!

@Mrs D: infinite! I did like four dresses, four sweaters, five pairs of leggings, three jeans, two skirts, two tights, six shirts. They all mixed and matched. We also got quite a few gifts, but her main wardrobe was all mix and match. It really helped so that she could pick her clothes and not look like a disaster.

I've started laying out stuff I already have (have me downs, stuff that will still fit, things I bought ahead) and looking through the new lines for the higher end stuff to see what special pieces I might want. From there I go through and make a list of what I need to fill in the gaps and to make the biggest number of outfit combinations.
I aim for 1-2 special occasion outfits, 2-3 dressyish outfits for like going out to dinner, birthday parties etc and about ten play outfits. We typically end up over in some category but it's usually from awesome deals or gifts etc.

I buy a lot (and sell after using for similar amounts so can sort of kind of justify). I also WOTH full time and prefer to do limited laundry. I also change her if we're going to my stroller fitness class after daycare since she's usually messy, and on weekends she'll often go through more.

10-12 long sleeved shirts.
4-5 hoodies
3-4 cardigans/sweaters
3-4 jeans
4-6 skirts
2-3 leggings
As many tights as I find on sale
5-6 winter dresses (if I'm being good)
3-4 shorts
6-8 short sleeved t-shirts
5-6 summer dresses (if I'm using restraint)
1-3 winter coats (I plan on one but this year I have 3 bought for a whopping $7 combined, one NWT)

I live in a place with very brutal winters that last forever, so I go heavy on winter clothes. I also try and dress DD in Christmas themed clothing from the day after Thanksgiving until Christmas, which usually entails 2-3 dresses and a few tops. I thrift for this all year and sell it on consignment the next year where I typically break even.

I plan for outdoor gear. It's the most expensive and we generally need 2 sets since preschool requires a dedicated set. It gets cold around these parts and LO attends a nature preschool, so it's really important for me to know she's warm and comfortable even if she's rolling around in snow all day. I usually stock up on clothes whenever there's a sale. Once a season, I access her clothes and replace anything that's getting small. Clothes are finally looking used -- so I'm looking forward to replacing some of those. I only shop for functional, everyday clothes. Nothing fancy unless it's for a special occasion.

@oliviaoblivia: do you mostly buy from one store? I'm very intrigued by this, but i'm not sure i'm organized enough to do it from multiple places.
I usually get basics from old navy and then some stuff I love from more expensive places. But between the stuff I get her used and all the different stores....she ends up with a mismatched wardrobe

I kind of try to do this, but most of his clothes are given to us by aunts or hand me downs. Before the major seasonal kids salea in town, I take stock of what we have for the next season and buy enough to just barely make it (usually pjs, coats, shoes, hats, and some pants). The rest of his wardrobe is presents and he often winds up with too much!