1. Prefer dark colors and patterns over light solids.
If you're like me and stains drive you nuts, you should absolutely lean towards darker colors and patterned clothing instead of plain, lightly colored items. I'm not saying I don't buy any lighter hues for my sons, but for things like play clothes and pajamas, dark colors save me SO MUCH TIME because even when they do get dusty during outside play and dribbled on during meals or colored on during crafts, I don't usually have to worry about stain treating in the first place because I know I won't be able to tell once I take the clothes out of the washer that they got so dirty. And if I do have to stain treat, the chances of having to repeat the process again because a stain is still visible are so slim. Whereas with the creams and whites... I often find them ruined by stains I can't get out and I'm left thinking, "WHY DID I EVEN BUY THAT?!" My kids have navy blue hoodies and cream hoodies. You can probably guess which color I consider the wiser purchase. ;)
2. Shop in outfits and keep overall color schemes in mind.
I have become more and more convinced that it makes sense to shop in outfits. For instance, if my son needs play clothes, I buy a top and bottoms that I know match. Easy outfit. Or, I make sure I already own something that will match whatever it is I'm adding to his wardrobe. This avoids the frustration of having separate pieces that don't actually go with anything else and therefore never get used! (Or maybe I'm the only one that happens to?!) Beware of having one pair of pants that go with many tops. I make this mistake sometimes and I can never cycle through the tops enough because the pants aren't clean often enough, so the tops really don't get as much use as I'd like whereas the pants are constantly being used. I also like to make sure I have flexibility with what can be worn with what. I try to keep color schemes in mind and purchase separates that will go with other separates. I have weird pet peeves (for some reason navy blue always gets me) but it definitely helps to try to create a wardrobe for a season that is cohesive so you have some flexibility with mixing and matching!
3. Keep comfort and ease of cleaning in mind.
I'm all for stylish kids, but remember that kids are meant move, explore, get dirty, etc. Don't spend a fortune on clothes they're going to ruin the first time they wear if it's going to stress you out. I try to buy my boys play clothes I don't mind aesthetically but that wouldn't necessarily qualify for outfit of the year! This is particularly important in summer. My boys live in lightweight shorts and tops that get changed often (they might go through several outfits a day) or in their bathing suits. In winter they tend to stay cleaner because they wear their snow clothes outside but then I'm constantly washing snow clothes! Which leads me the second part of this tip... things that aren't machinable washable are probably NOT going to be your best bet. Some weeks I am washing coats and gloves and snow pants on a practically a daily basis. The "hang dry only" or "hand wash only" items get old really fast!
4. Try before you committ.
I really find it essential to try clothes on before I commit to keeping them, both for myself and my kids. It's really common for toddler clothing to fit for length but he HUGE around the waist with no way to adjust the width. So annoying! Certain brands are worse than others, and even within certain brands some styles work and some don't. I shop online a lot so I can avoid taking my kids to the store with me, or I save receipts and make returns when necessary. Bottoms with adjustable waistbands and functional drawstrings can make all the difference!!!
5. Don't over buy.
I like my kids to use the clothes I buy them. It seems so wasteful to me to have clothes they never wear because they're either impractical or they just have too many clothes to cycle through everything! My boys have a select few "nicer" outfits for church or events but most of their clothes are qualified as classic kid clothes- leggings, sweats, tees that allow them to be comfy on a daily basis. I mean if I'm going to be completely honest a lot of days we don't change out of our PJs until bedtime... when we put on a fresh pair.
6. Buy in advance of the start of a season.
I like to begin planning for the next season before it arrives so I have a few outfits on hand for when the weather start changing. This way I don't find myself in a pinch with warm weather and a child who only has sweatpants and long sleeves to wear. I do add items over the course of a season but I mainly buy a wardrobe early to the start of the next season when there are a lot of options and I can take my time and plan outfits and such. Also, stores start breaking out clothing for the next season ridiculously early and it's the middle of winter but you can't find a winter coat! So you have to plan ahead if you want the best variety.
7. Remember that your toddler is G R O W I N G!
Things tend to be bigger at the start of a season and fit better towards the middle/end of a season. Kids are always growing, it seems! If something fits perfectly at the start of the warm season chances are it's going to be too small by the end of the season. Try to factor in that your child will grow over the course of a season! I don't like when my kids are swimming in their clothes but I also realize it's not financially responsible to have to buy them two sets in a single season because I didn't just deal with something fitting a bit big initially. Now with newborns and babies this is different because they grow SO fast. Also, I live in Pennsylvania where we have 4 distinct seasons so obviously this won't apply perfectly to every climate.
8. My top shops!
I would estimate that 95% of all the clothes my boys wear are from the following stores: Gap, Old Navy, Hanna Andersson, and Carter's. We also love Baby Bogs, Patagonia, and L.L.Bean for outerwear! I like Zara but their sizing for toddler boys is CRAZY and frustrating. Hanna Andersson is amazing because you can return anything for any reason at any time. If at the end of a season I realize my kids barely wore something I purchased from Hanna Andersson, I'll send it back for a refund, even if tags have been removed and it's been washed and worn. If from Hanna Andersson wears out before it seems like it should, I'll send it back! L.L.Bean has the same amazing policy, and I believe Bogs and Patagonia have very similar policies. It's worth spending the extra money (in my opinion) on brands that stand behind their products. Plus almost all of the store mentioned above regularly run really decent sales, so you never have to pay full price (except Patagonia, I pay full price there). I also recommend checking out secondhand shops like Once Upon A Child as they tend to have good variety and good prices.
9. Buy organic PJs.
My kids spend the most amount of time in their PJs, so I buy organic. We have some non-organic PJs from before I implemented this goal for myself, but I mainly purchase them Hanna Andersson during sales. I also aim to do organic undies!