It isn’t always what you want to do, of course, but it is probably something you always want to be able to do. In Abraham Maslow’s well-known hierarchy of needs, “fitting in” and “not fitting in” are adjacent goals. My University of Oregon mentor, Jim Davies, who was a careful student of Maslow’s work, used to say that we wanted first to be a part; having achieved that, we wanted to be 
Cute.
I’m thinking about the move that Bette and I will be making to a retirement center later this month. It’s a little like moving to a new school. You look around and see what clumps of people there are and you decide which group or groups you want to be a part of or that you don’t want to be a part of any group. [1]. I’ve never done this at a retirement center before, so I’m trying to anticipate, what the process will be like.
I’m guessing that there is a rough sorting of the residents by mobility. There will be people like me, who can walk out the front door and go anywhere within walking distance just by deciding to. There will be people who can walk a short distance if they are careful. Then there are the people with walkers and wheel chairs. Then there are people who need for someone else to provide the push for the wheel chairs. For now, I fit best into the category of people who can go wherever they want. I doubt that this category is also a group [2], but I am not opposed to starting with a category.
There will also be a sorting by mental ability in the very rough sense of recognizing other people and having conversation. I don’t know quite how those categories will shape up, but I very much hope that I will have access to people who like to read and think and talk and who are likely to remember on Thursday, the conversation we had on Tuesday.
Within this category, I imagine that people are different from each other more by preferred style of interaction than by ability. Some people like to sit together and share stories of their grandchildren and their pets. Some people like to talk sports; it is their soap opera. Some people like to harangue each other about moral or religious or political issues. It is the haranguing, more than the topics, that makes them a viable group.
When it comes to conversations, I know what I like, but I also know that you can’t always get what you like. And I know that knowing how to fit into a style of conversation that you would not have chosen is a very important skill. I practice that skill at our Starbucks nearly every morning. It I do it right, it will make me a part. There will always be time to set myself apart.
I know there will be other sortings as well; I’m just not sure what they will be. Will there be a group—a real group, not just a category—of “people who used to be teachers?” Will there be “people who used to run businesses?” Will there be a group who used to be important and miss it dreadfully? Will there be a group of movers and shakers who serve on retirement center or on neighborhood committees and who want to tell you what is going on? I have no idea.
I am thinking, however, that there is a visual element to these groupings and the visual element is what I am thinking about right now. I know there is a tendency to get shabby and unkempt when you get old because no one actually cares about how you look. I don’t want to do that. On the other hand, I don’t want to turn suddenly into a clothes horse, which I have never ever been and which I would tire of. Bette could be a clothes horse if she wanted to; I’m pretty sure I wouldn’t tire of that.
But apart from “not grubby and not classy,” which is pretty broad, I am sure there are ways of presenting myself that will invite some people to want to know more about me. I already know that they will be presenting themselves in ways that affect me that way.
I recently wrote a very brief biographical statement, as the Director of Resident Services asks of all the new people, and I tried to tuck into it little indicators of who I am and what I care about. What I would like, from that little bio, is for some people there to read it and be interested in meeting me and for other people to read it and decide not to. I actually know how to do that with words. In this essay, I am trying to imagine how to do that same thing with how I look. As you can tell, I have no idea how to think my way through that.
I know this happens all the time in new settings. I know I am going to walk into the dining room and look around. I am going to see some people dressed as “we used to be teachers” or “we used to run businesses” or “we were stay-at-home moms.” And they are going to look at us, at “the new guys,” and make the same kinds of early decisions. Where is the Sorting Hat when you really need it?
What I will do if I don’t get any kind of a handle on this process, is just to continue looking, as we become part of the Holladay Park Plaza community, the way I look now and see what happens. There’s nothing really wrong with that, but if I could understand the process better, I could do something on purpose—and I love doing things on purpose.
[1] I discovered well after I graduated from high school that back when I was there, I was considered to be a member of “the smart kids.” More a category than a group, I regret to say, but even so, I would have appreciated knowing at the time, that people thought I belonged anywhere.
[2] I use the word category to refer to any collection of people who share certain traits. Left handed catchers whose mothers immigrated from Puerto Rico, let’s say. But a group is interactive. People know each other and choose their behaviors based on likely responses. That’s what I am going to mean, in any case.
The Dilettante's Dilemma 
There are undoubtedly groups that exist at Holladay Park Plaza. On any of your visits, have you looked intentionally at the way “they” dress? That may give you a clue if you’re looking for a way to communicate to them that you can be “a part.” But I believe you can approach your dress in the same way you approach your writing!
The thing that first came to mind while reading your post was the comment made by our school board attorney as he spoke to my tenth graders about his occupation, part of a Teach-In program in which community people came into our classrooms to speak about their professions. He said he always wore a black suit, sometimes double-breasted, depending on the seriousness of the case, for opening and closing statements, but a light blue or grey suit for handling testimony because he wanted to the court to be sympathetic to his arguments. So he used what he knew of the psychological effect of colors to influence his audience.
Well that just seems the same thing to me as controlling the tone of an essay, the words and devices available to “color” meaning. Consider all the clothing color options you have: “loud” and flamboyant; light, or dark and conservative; cold, warm, neutral, pastel,—can you feel the tones shift as you imagine yourself wearing each of these? Then there are solids, which, depending on the color and shade, may appear plain, like Saxon words that don’t call much attention to themselves. Plaids and prints may be bold or soft, but can also convey something about the wearer—they may be common or playful or unique. They may betray an allegiance, like a Ducks sweatshirt or a Portland State tee (in writing, we’d probably call it a prejudice).
Then there are the accessories to consider, like adornments to basic prose: sport coat or cardigan, leather belt or alligator (i.e., the flair of an interesting simile, metaphor, or other imagery); a tie (formal construction), or cravat (hyperbole), or open collar (ellipsis)? Watch or other jewelry—the sparkle of syllepsis. Shoes? Headwear? The epanalepsis of matching hat and shoes? There is as much that can be done with dress as can be done with a string of words in a sentence.
And you’ve already addressed formal/informal attire, but there is such a range in between, mostly tied to purpose and context. Like the slang or profane, there are working-in-the-yard or painting-the-garage grungy garb. There are picnic informal, grocery shopping informal, and meeting with the neighbors informal—all different grades, but, again, most like Saxon in origin, especially as opposed to the richness and finery of your Greek and Latin. Which leads me to consider both the language and haberdashery of modern nationalities: the ease and grace of French, the opulence of Italian, the liveliness of Spanish. German? Gee, I guess practical? Unadorned? Back to the Saxons again.
In short, you may have the same options for your dress as you do for your language, and the clothing options have effects as language options do. On the other hand, you have already established the way you use language; perhaps the best course is to continue to dress in the ways that you already do. It’s what’s worked so far!