My LO has insisted on picking her own outfits for the past month or so. I thought it would be a quick phase that lasted a week or so, but it's still going strong. Most of the time it's unmatching and often includes a fluffy skirt. Her teachers said as long as she's dressed it's all good 
one less thing I have to worry about!
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I try to steer her towards certain things and put my foot down about weather appropriate things (long sleeves and pants or tights if it's a dress). Otherwise, whatever. I have too many battles and she has strong opinions! Any time I buy her clothes I make her look at them with me and tell me if she likes them and will wear them.
ETA: she is almost 3.5 and has been this way for a while.
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I give her a choice between 3 shirts and she'll still let me pick matching pants. But sometimes she'll want to wear the same dress 3 days in a row.
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Once. This happened - he may not have been ready for the responsibility.
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Yep. My daughter has been picking her outfits since she turned two. Now, she even gets dressed by herself. As long as it's weather appropriate, she can wear it. She has really been into tutus over the last few weeks. My son picks his own clothes, but he's nearly 6.
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It comes and goes. She's now 4 and I usually get away with suggesting 2 outfits and letting her pick. But sometimes she refuses completely. It's an improvement - when she was 2, she wanted to pick every single thing by herself. It was rough (especially when pressed for time, which is usually the case in the morning).
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Oh yes. She's 3.5 and insists on picking out her clothes, seems to be a trend with those above because nearly everyday she wants to wear a tutu. I do steer her to things that aren't terribly mismatched, and she's good about staying weather appropriate- even though a lot of times that's means putting pants under a tutu.
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Yes, my 3.5 year old chooses his clothing for the next day the night before and then gets dressed by himself in the morning. I love that he is so independent.
I can see my not quite 2 year old following in his footsteps. She definitely has an opinion when we choose her clothes together. She's also able to put some of her clothes on herself. With soon 4 kids in the house it's a good thing.
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Nope! She doesn't know it's a thing. I pick out the kids' clothes the night before so everything run smoothly in the morning. Sometimes she asks to add a necklace or something.
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Yes. For the 2.5 year old, I give a few options. She generally changes to a ballet outfit or princess dress at the first opportunity anyway.
For the 4.5 year old, I let her choose her school outfit but retain veto power, particularly if she's not following the rules (no formal dresses, no footed tights at school since she has to take them off for gym and I don't want her bare legged/flashing her undies the rest of the day, nothing really weather inappropriate - though her classroom is so warm I sometimes relent on this one), and nothing I'd be really upset if she ruined. We've had a few paint episodes recently and she spoiled her favorite old navy tutu dress.
If we were going somewhere other than school, I'd probably try to choose something cute, but she has very strong opinions. She's pretty good about matching colors, she's just a little more fashion forward than I am about print mixing, haha. I like everything in her wardrobe, so it's not TOO big of a deal to me - and a lot of the mismatching is cute. Her favorite outfit is to wear everything doggie that she owns all at once - a doggie graphic tee, doggie print leggings, and a (non matching) doggie print skirt, with doggie socks. It's ridiculous but I admire her confidence in her choice. In our new house, where she will use a closet rather than a dresser - I'm considering hanging outfits together to claw back a little more control.
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@erinbaderin: hahahaha!
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I do let my son pick what he wears, but I do control what is in the drawers very strictly, so it's always weather appropriate and not a costume. Right now, he wouldn't be able to pick a short sleeved shirt unless I got it down for him, so it really doesn't matter if it matches.
I put school clothes away by outfit, pants and shirt together so he just grabs one from the hanging organizer.
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DS1 picks out his own, and has since around age 2. We only put weather appropriate clothes in his drawers, though, and we shop together for clothes we BOTH like. It does mean that he has a Star Wars or Minecraft shirt for every day of the week...and tons of camoflage...but it works for us. DS2 isn't anywhere near interested or willing yet, though he's still really young for it (18 months); he's just now learning to take off/put on a shirt.
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My daughter has strong opinions so we have 'school clothes' and 'weekend clothes'. School clothes are either already stained/trashed/cheap brands (Gap, etc) and weekend clothes are the nicer stuff (Boden, Hanna, etc). Ain't no way I'm letting her get paint all over her Boden, haha! My son doesn't care at all what he wears so I still get to pick out his clothes, yay!
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Neither boy (4 and 2.5) cares what they wear. Makes it easy for me
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Yep. DD1 has picked her stuff out, or at least had an opinion about it, since around 2.5, and DD2 (just turned 2) is starting to voice hers now as well. As long as it is seasonally appropriate (and I've definitely let her wear a sleeveless dress with a long-sleeve over or under!), I'm pretty indifferent.
We have a lot of plain-colored basics, so there isn't really too much she can pick out that looks super ridiculous. And I do try to exert a bit of control/influence on special days like picture day! But even then, it usually has to be options for her to choose from.
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Yes. DD is almost 4 she picks her clothes out 99% of the time. She doesn't always match and she loves to wear 2 different shoes when she isn't going to school. She reminds me a bit of Punky Brewster. Honestly it doesn't matter if she matches and it drives me nuts when an adult likes to point it out because it makes zero difference.
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Bedtime yes, she picks her jammies!!! I may have to wash a few sets daily.... lol
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Nope. She's 4 and doesn't care that much. I pick out a week- 2 weeks worth of clothes and hang them in the closet. Makes it easy during the week and easy on DH if he needs to pick an outfit.
Sometimes she has an opinion and I try to respect it since she mostly let's me do what I want.
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@erinbaderin: BUT - matching slippers! I think he's totally ready.
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