Mo, I think times worn can be a factor, but I don't think it's the only one. I think that if you can remember back to the first time you wore it, and realize how different your life was back then, it seems old. I have a red dress that was purchased for my 8th grade graduation, and I wore it to my Aunt and Uncle's wedding. I've worn it less than 10 times. I'm now in the equivalent of 19th grade, and my cousins are 4 and 7! That dress feels a hell of a lot older than the boots I bought in 2010 and have worn 122 times!

I love how Kate describes things-- using tortoises and "19th grade", she is awesome and I agree with her here completely in both the posts.

Plus-- honestly unless it is a fancy outfit or extreme seasonal items, anything worth wearing probably should be worn more than 4-5 times a year imo-- that isn't even once a month during a season! Sure, there are some things that you might only wear for three months (shorts in CO, coat in FL)-- but in that case, you probably don't need as many!

Hm, I don't tend to think of "age" in terms of my clothes. More in terms of "condition" and "timeliness." So I guess "old" to me would be something that's outlived its usefulness, no matter its chronological age. I have some underwear that's going on 15 years, haha!

I think it would be nice if datedness and worn out ness happened at the same time. In fact I aim for that to happen, by trying to only buy enough trendy things that I will wear frequently and thus wear out quickly. (Although this could still mean up to 3 years!)
Of course this is hard to orchestrate precisely. And I have dresses bought 12 years ago, and over 10 years ago that I still wear regularly, though others I have bought since then look dated.

And then with basics I have things that are getting worn out that I would happily buy the exact thing again.

I have a gorgeous long, white dress which I wore once, 18 years ago. I wouldn't get one leg in it now though ....

When I was in grad school, I was still wearing stuff I had from high school, so age didn't impact what I considered to be "old."

After having two kids, I've put on a few pounds and my body shape has changed, but I still have a few dresses/tops/skirts stashed in a box that I hope to one day fit back into. It's labeled "Banananutmuffin's Skinny Clothes." lol

Formal dresses, business suits, etc.... I have some that I've had for 10 years. A few I should get rid of because they are just too young looking for me now, but I haven't done a major closet purge in a while.

I do tend to buy what I consider to be classic lines - nothing very trendy, everything pretty simple. So fashion-wise I think much of my wardrobe stands the test of time.

I am more likely to quickly get rid of things that were trendy but have ceased to be so. I don't buy many of those types of pieces, but every once in a while I do, and they have the fastest turnover in my closet.