If you are of a, errm, certain age, do you think about “retirement” planning re: where your wardrobe is going?

I’m not retirement age—no way! But while enjoying my working wardrobe updates and branching out in casual wear, I’ve also been pondering the whole timeless and investment hooey thing from the nearer-retirement-than-not angle. So many things I’m wearing now, I’d have much less use for, and other “capsules” would need to expand, and perhaps whole wardrobe should shrink (figuratively).

What this means to me is that the generic skills of style reviewing and updating are as important as what exactly is in my closet now. Also (being a broken record and still quoting Gaylene after a year or more), not going too overboard in one area—even workwear, which is my biggest activity capsule. Being much more on a 2-3 year clothing cycle and not a 10-year wardrobe-building plan, not because of "fast fashion" but because of life changes. If I were also to be very practical. I’d say I’m starting to think how to start cross-dressing (!) more.

I know that many of you have faced challenges when making major job changes or any major change in lifestyle, or even moving to a new climate. I’m wondering how much to think ahead. As I said, I don’t think it’s time to actually buy different clothes, but to have fun thinking about which items might stay or go, and which ones I really enjoy in or out of the work environment, and why.