There is an interesting thread on Pattern Review about how to edit your closet, and it got me thinking as to what my criteria are. Not that I am not, *ahem*, overdue for a major closet weeding. I pull random things on a regular basis and put them in the giveaway pile, but I haven't done a systematic cull in a while.
A couple of years ago I made the decision to Look Cute Every Day. I don't mean this in a "be decorative" or "attract men" or "be presentable because if you don't make yourself pretty you are a blight upon humankind" kind of way (please see this fabulous post by Erin at Dress a Day for a more coherent explanation of what I mean)--it has entirely to do with how *I* feel, and I am happier when I Look Cute.
I'm not 100% there, but I am much closer than when I started (now I feel cute probably 90-95% of the time, versus about 70% before). My solution--and this isn't for everyone--was to ditch "practical" clothes that were totally functional but I felt blah in--plain t-shirt tops, plain work pants, plain anything. I would rather wear a dress than pants any day...and now I do. I'm not talking about a straw man of frumpiness here--I mean even in well-fitting trousers and a good quality solid colored top I just don't feel Cute, so I don't wear them. Your mileage will vary.
Cleaning out my closet involves answering a single question: "Do I Look Cute (i.e., feel cute) in this?" Not, "Is this useful? Is this a staple I 'should' have? Is this in good shape? Does this fit well?" All of those questions get you part of the way there...but they don't guarantee you love the piece in question and that you Look Cute when you put on. It's silly to keep clothes out of an obligation--they don't have feelings and there is no Tally Sheet in the Sky that puts a black mark next to your name for getting rid of serviceable clothes you don't like--but I used to do it all the time. I'd keep a perfectly good item of clothing that I didn't like wearing just because it was perfectly good. Perfectly good is not good enough!
I am not a mom, and I know that changes things (a lot), but when I hang out with my many nephews and niece I still look cute--adorable polyester knit dresses wash up just as well as boring polyester pants. When I met my twin nephews for the first time Fox spit up directly into my cleavage and then overflowed his diaper into my lap. I also crawled through a foul, disgusting playland with the older kids. The next day I played baseball with my other nephews in another cute dress. As long as you're not afraid to get cute clothes dirty, you can wear them every day. Cute Clothes are generally not more expensive (or more difficult to make) than "serviceable" clothes. It seems more of a tragedy if they get ruined, but it's actually not. Don't fall into the trap of Too Good To Use (which is a whole other rant).
Another aspect was finding a way to describe my style, which is "Retro Fantasy." When I'm contemplating what to sew, I can ask myself "is it retro? is it fantasy?" If neither question can be answered with a yes, I probably won't love it so I look for a project I will love.
There are issues.
Because cute clothes are more often distinctive I have a *lot* of them so I don't feel like I'm wearing the same things over and over. Acquisitiveness is not a virtue, even when you acquire all those clothes by sewing. Minimalist and low impact I ain't, and this disturbs me sometimes with all the environmental and consumerist implications.
There is also a concern about shallowness, and focusing too much on looks. This is a personal balance issue. You have to get dressed every morning, and you might as well Look Cute. Once I get dressed I don't think about it much for the rest of the day, although I might occasionally look down at what I'm wearing for a little burst of "I look cute!" confidence. The rest of the day my focus is on my career, my friends, working out, reading good books, etc.
You also can't Look Cute if you hate yourself (because Cute isn't objective--it's a subjective assessment of yourself by yourself). I wish I had some advice to offer here but I don't. The best I can say is that when I am depressed (the chemical kind, not the situational kind) I hate myself and nothing will make me feel Cute. I've tried medication but unfortunately didn't find one that worked, but exercise has been proven to be as effective as a mild anti-depressant so I exercise.
And adequate omega-3 fatty acid intake has also recently been shown to treat depression. I am allergic to walnuts and don't eat fish because I'm a vegetarian, and these are the major sources, so until recently I have NEVER had adequate omega-3 intake over the course of my entire lifetime. After reading Dr. Walter Willet's Eat, Drink, and Be Healthy I started taking flaxseed oil capsules (fish oil would probably be better, but there's the vegetarian thing for me) and sprinkling ground flaxseed on my morning oatmeal (also a good source of fiber!) a few years ago and it has made a huge difference in my mood. There have been confounding factors in that my life in general has improved, but I do think that giving my brain an essential nutrient of which it had long been deprived has made a difference (and a neighbor has had the same experience). I am not a pills and potions kind of person, but clinical research and my personal experience say that this is a pill that is worth it. Even better if you can eat the foods from which you can get it straight from the source.
When I address my depression and don't hate myself it's a lot easier to feel Cute.
And of course we all have our body issues (everyone is well aware of my obsession with my belly). But I have seen evidence that any size, shape, and age can Be Cute.
But there is a bit of a chicken-and-egg thing here. You don't have to wait until you love every aspect of yourself to Look Cute Every Day. You can look cute without *feeling* cute...but eventually the feeling cute part will tag along.
Look Cute Every Day might not work for everyone, but for me it is a useful wardrobe philosophy, and contributes a great deal to my happiness.