My favorite t-shirts, once they grow too holey for public wear, graduate from the t-shirt drawer to the pajamas drawer.
This just pushes the question back to "how do you handle your favorite pajamas," though!
I wear my favorite new shirts (socks, underpants) a little more often, but then as they get less new and I worry about washing them that often, I wear them less.
So, my favorite camisole with bralet is wearing out, and I therefore only wear it when it's the only thing in the right color, or something. But I was just given a new football hoodie, and I appear to be wearing that constantly.
Ah! I think I can see the graph of that in my head, and it makes sense to me.
I picked special occasion and then realized that doesn't quite capture it. Favorite things are in the rotation every laundry cycle but I strategize which day of that cycle they'll be worn on (and will pick whatever less-favored items to fill the less-special gaps).
I do that. I especially do that with things on delicate wash. With darks (I hardly ever wear lights--most of the lights in our wash are not mine), we do enough of them that if I happen to miss a laundry cycle, it's not that big a missed opportunity. But I don't wash delicates all that often, so I strategize making sure I get them in before the next time I do delicates, and also which day.
I dress for other people sometimes. Most notably I dress for my goddaughter, because she is the person who most clearly appreciates particular kinds of pretty things and has joy in them that is not problematic or weird. Also for my mother for the same reasons.
They're my favorites, so I wear them a lot (or why have them?) and then have a sad when they inevitably wear out. At the moment I have several shirts in the "denial" phase: "Those holes? They're barely noticeable!"
On the other hand, finally having to discard favorites is also an impetus to cull the pristine unfavored T-shirts and search for new favorites.
Do you find that works? I almost never find that things that were previously unfavored are favored once something else wears out. They remain "things I wear that are all right" (because if things are not all right I do not keep them around), but they never really join the ranks of "favorite" belatedly.
I think there's some sort of curve: wear more when I first get it, because hey, cool thing! And maybe "cool thing I want to show people" if it's cool largely for the pattern/appearance. And then it gets to "save this for special occasions," because I like knowing I have, say, a purple sweatshirt with a dandelion printed on the front.
And then there's the stuff that I can't bear to toss, and is still physically functional, but can be worn only for some odd value of special occasion, like the bleach-stained blue shirt that I am hanging onto because they aren't making them anymore. But I can wear that at home, or to go to the grocery store, but I'm not going to wear it to a party, because it's obviously stained.
Special occasions, where 'special occasions' seem to come up about once every two laundry cycles.
I wear the garment all the time until something happens -- a thread snagged by a cat's claw, a turmeric stain. Then I fix the problem and add rules -- try not to wear while sitting at the computer or cooking, just don't ever, ever put this thing on in the spring when you will wander out to see if the crocuses are up and end up getting all muddy doing yard work.
I actually really hate having "good" clothes that I only wear sometimes, but am always backed into that corner by failing to keep the cats' claws trimmed, failing to put on an apron when making curry, and so on. And though I am sad when things begin to wear out, there is a secret delight in the fact that now I can wear them around the house and in the yard without worrying, because they are too far gone to wear in public anyway. They almost always retain their charm for me even in a decrepit state.
I have at least managed to get into the habit, if necessary, of changing my upper garments completely before making dinner, if I have had lunch with my mom or whatever earlier in the day and therefore put on something I like.
I am also eventually likely to wear out, after all.
When I got MS, and after watching various friends deal with cancer, using my favorites had a different meaning for me. I'm going to use/play with/eat my favorites *now*, not in some mythical future that may not happen. But that's just me.
For me, for a favorite that is hard to replace, it's: wear a lot until it starts feeling like it's showing wear. Then wear on special occasions. Then once it gets holes but is still wearable, wear it a lot again but for things like sports and physical activities, where I don't care as much if it rips because it's already mostly dead.
I said "save it for special occasions" but it really depends on whether I can get another one of whatever it is. If I can easily get another one, I will wear it more often. However, most of the things I think of as favorites are not easily replaceable.
Most of the time, I wear my favorite things more often, because they're my favorites, and why not enjoy them? But I have a few things that I expect will be difficult to impossible to replace once I wear them out, and I tend to ration those because I will be sad when I finally have to admit that they are too worn out.
I don't have a system, but I do wear my favorite hot-weather shirt very rarely, because it is cursed.
Every single time I wear it, something unusual and stain-producing happens. The first few times, it was me being clumsy, so I vowed never to eat, clean, or cook while wearing it. The next time I put it on after taking this vow, I was crossing a crosswalk, which was full of a great many people, and a small child going in the opposite direction smeared my torso from the bust down with chocolate ice cream, a thing which has never happened to me before or since. The time after that, a bird, from midair, was not housebroken.
I'd like to wear it more often. It fits very well, and the design on it is amazing, and it was the shirt my department in college put out my senior year and has all sorts of good memories associated. But the thing is cursed and that's all there is to it.
My bird curse has not been active for years but seemed to be tied to my person rather than a particular garment.
Wear it more often and immediately begin to look for sources whereby I can stockpile more. I tend to like clothing because it fits well/comfortably/is sturdy/well-designed (as opposed to, say, because of color or pattern), and when I find something that works, I stick with it for a LONG time.
(Clothing that I like for style reasons - like T-shirts which have sentimental value to me, such as my no-longer-available-in-any-way Rocky Horror Picture Show shirt - get worn heavily until they are just on the verge of collapse, and then get stored in a drawer as keepsakes.)
Your first paragraph, me too. The better I like something (especially a purse) the more I look for a spare, or an upgrade.
If it's something practical and favorite because comfortable, I wear it constantly.
If it's something dressy, and favorite because of appearance, I save it for special.
It it's both, I wear it constantly. Comfort triumphs.
When I find something I really like that fits me well, if it's still available, I will go buy more copies, either in the same color or a variety of colors. I will wear it when I want to feel good, but not on any schedule. Since I can sew, another option is to try to make a pattern off it and make more. If it is totally worn out, I take it apart to make the pattern. I did this with a favorite nightgown, and I'm still wearing a copy. Also, I go to Savers on "Geezer Day" Tuesdays when clothes are 40% off for people 55 and over. At Christmas time, I found an exact copy of my favorite Christmas sweater, in better condition than mine, so I bought a second copy. Talk to me if you want to see about making a pattern to make a copy of something you love.
It has gotten to the point where members of my family will say to me, "Okay, good, go get another one," when I am at the checkout stand with something I particularly like.