Dressing yourself is one of those things you can’t just learn once and be done with it, which is pretty much the definition of an intractable problem.

I think most of us dream about figuring it out. Much like Steve Jobs with his black mock turtlenecks and 501’s, Barack Obama has his wardrobe down to a routine: either a blue or gray suit. Though it isn’t just rich, powerful men who think this way: Timoni West, a designer at Foursquare, got a lot of attention for her post about wearing a hoodie, t-shirt, tank top, leggings, and a skirt every day.

Even artists struggle with what their characters should wear. Charles Willeford, my vote as America’s most under-recognized great novelist, has his recurring character, Hoke Mosely, adopt the routine of wearing the same yellow, poplin jumpsuit every day in the unpublished Grimhaven.

What clothes to buy, and when and how to wear them, is bewildering. I needed new jeans recently because the only ones I had no longer fit well and were beginning to fall apart. So I read dozens of articles, watched a video, shopped at far too many online and in-person stores, and corresponded with a friend who knows a lot more about clothing than I do. I ended up buying some Uniqlo jeans and a pair of Levi’s shrink-to-fit 501s. I’m not endorsing either, though I think these were good choices for me, primarily because they fit my budget and my body pretty well.

During the course of shopping for these jeans, I made a list of all the things I consider when buying clothes:

  • How much does it cost?
  • How much does it cost compared to other, similar items?
  • How much is it discounted? Is this discount frequently available or is this somehow special? Is the price unique to this situation?
  • How much is it worth to me?
  • What does its price say about me?
  • Is it in new or relatively new condition?
  • Is it being sold in a secondary market (thrift store, consignment shop, eBay, Craigslist) but still have its tags?
  • Can I try it on?
  • Does it fit?
  • Is the cut flattering?
  • How quickly will the cut look dated?
  • Should I get it tailored?
  • How will it look if my weight changes?
  • Is the color or pattern right for me?
  • Does it go with other items that I own?
  • How frequently can I wear it?
  • Are there situations in which I’ll wish I had it?
  • Is it like other items in my wardrobe that I like and wish I had more of? Does it replace an item that needs replacing?
  • Have I bought anything from this seller or manufacturer before?
  • What do people I trust think about this seller or manufacturer?
  • What have a read or heard about this seller or manufacturer?
  • Is the item well made?
  • When was it made?
  • Where was it made?
  • Who made it and what were the working conditions (children, slaves, union workers, an artisan)?
  • Does it advertise itself or its manufacturer or some other entity, either explicitly or implicitly? Does it have any other text or images that I would be seen as communicating, either sincerely or ironically, if I wore it?
  • Is there anything else about it that would make others think that it affiliated me with a specific group or ideology, and how do I feel about that?
  • What is it made of?
  • Did any animals have to suffer or die in order for it to be made?
  • Is the material used in its construction sustainable? Organic?
  • How difficult is it to clean? How often do I have to clean it? Does it need to be dry cleaned? Ironed?
  • Is it comfortable?

The list of things I consider when deciding what to wear each day is shorter, but related:

  • Is it clean?
  • How’s the weather? The temperature in the buildings where I expect to spend my time today?
  • Where am I going today and who am I going to see?
  • How recently have I worn this item or this outfit? Did I wear the same item or outfit this day last week? The last time I saw this same group of people?
  • Would I prefer to hold off on wearing anything until tomorrow, or this day next week, or the next time I’m going to see this same group of people?
  • Does this outfit look all right?

Unlike Jobs, Obama, West, and Mosely, I don’t particularly want to simplify my wardrobe. I like the idea of dressing somewhat differently each day. I enjoy reading about fashion in places like Unrefinery and having Jesse Thorn tell me to Put This On. Finding clothes I like at thrift stores and consignment shops is satisfying, and it can also be fun to try on new clothes at pretty stores.

I feel confident when I wear the right clothes at the right time—when what I’m wearing and how I’m wearing it meet the criteria I identified above that seem relevant to the given situation. I don’t feel like a celebrity, as though any signaling I may be doing should make people like me more or give me extra attention. For me, it’s more resembles the idea of flow: like I can forget about the distractions associated with not feeling comfortable in the situation and focus on the matter at hand. Mentally, it feels like sleeping somewhere remote: I generally don’t realize how much ambient light and noise is around me, and how distracting they can be, until they’re absent. That’s how it is with clothing: I don’t appreciate how worried I am about my appearance most of the time until I’m wearing something that doesn’t make me anxious.

It seems this anxiety is pretty commonplace, even among other librarians. While we don’t have a uniform, as with many other professions there are a few librarian looks we can choose to conform to or reject, either of which should serve as a useful starting point in deciding what clothes to buy and how to wear them. And yet the library community seems as infused with clothing anxiety as I am, a situation highlighted recently by Sarah Houghton’s post at Librarian in Black entitled “Wear What You Want” and the discussion it helped to inspire (even though Sarah herself is comfortable with how she dresses).

For a long time I fantasized about having someone weed my closet and dresser with me, then take me shopping for additional clothes I should own. I wanted that to be a friend, though occasionally I tried to think of ways I could get one of those fashion shows to do it without actually making me appear on a program.

But now that everything is an app, I want software that makes it possible. Shopping for food and coming up with recipes seems analogous to shopping for clothes and deciding what to wear. For fifteen years, we’ve had websites that will tell you what groceries to buy and how to prepare them, yet there’s still room for innovation and good design (as well as a lot of excitement about the dietary equivalent of wearing a yellow, poplin jumpsuit every day).

So my new dream is an app that will analyze my wardrobe, suggest what to wear each day, and let me know about items I might want to buy. There are a few apps and websites that are beginning to approach this idea, including Who Brain, 123dressme, Pocket Closet, and the Male Fashion Advice sub-Reddit, but their heuristics and interfaces aren’t yet anywhere close to what I want.

Perhaps the problem is even more intractable than I want to acknowledge. It seems easy enough to take photos of my clothes for a database of potential outfits, photograph them again each time I put them in the laundry, and photograph them once more when they’re clean and I’m putting them away. But if it were that easy, someone would have probably built this app already. And if I were actually willing to spend several minutes each day photographing my clothes, I could probably instead use that time to learn how to buy stuff that looks good on me, and how to combine that stuff into appropriate outfits.