Lari, for me, I think wearing out my clothes before donation time is a great thing. But not as quick as one or two seasons in, way before I'm ready to be done with them. Hence, my mention of just the right size wardrobe.

Excellent point! I sometimes "save" my favorites and I think this is why.

Och, so true. I discovered this the hard way, when I did my move-in capsule. I was simply killing my basics, my foundation pieces. It felt like I had to buy a whole new wardrobe every month - especially because I couldn't really get the same pieces. Sort of threw everything off.

Very good point! I think we all have a slightly different happy number, but what you say is exactly why I keep my wardrobe at around 200 items. That is a good amount for me to have enough variety and for my beloved pieces to last a good while. The things I love the MOST most still get worn out faster, of course

This is a great point! I have definitely had some clothes and shoes that I really didn't want to stop wearing, even though they were now shadows of their former selves.

To pre-empt this, I bought second of a basic burnt orange top that I knew would be hard to replace (it was $8 from loft, pictured below), and have one in use and the other waiting patiently for when the first one gets worn out.

In another case, I wore my cognac booties into the ground, and had to literally put them in our garbage bin when it was super gross so that I wouldn't change my mind and go back for them. After a couple months of ebay searches, I replaced them with the exact same booties in a dark brown color.

On the other hand, I have come to realize that retiring worn out clothes is key to both not looking dated and keeping my look "current". Right now my 74 clothes are about 12% from 2010, 20% from 2011, 16% from 2012, 41% from 2013, and 11% from 2014 (that % is about to increase). For shoes, I have 1 pair each from 2010, 2011, and 2012, 2 from 2013, and 3 from 2014. Bottoms last longer, tops get worn out quickly (no matter how expensive they were...).

I pretty much wear one pair of sandals all summer long, and then have to toss them by the time autumn comes. I have fond memories of the different sandals I've loved over the years (two pairs included below), but I also think it's cool that I can look at a picture of me and know which summer it was based on which shoes I was wearing.

Personally, I would rather wear my favorite items all the time and wear them out, than save them and have them slowly become dated or forgotten. Tossing worn out favorites can be sad, but I can also look back on them proudly and with fond memories. For me, donating neglected items that I had high hopes for but could never fully make work or that were overshadowed by my favorites is far more traumatic.

I have this problem. I have a handful of things that everyone "needs" in their closet (in my case something that I don't wear much that will be in pristine condition to wear when I need interview, presentation, or funeral clothing), a few items that I wear only a few times a year (because they aren't quite right or they are special occasion things) and then my everyday clothes. Usually I have about 9 tops in rotation and 3-4 bottoms and 3-4 pairs of shoes + 2-3 jackets. Even high quality stuff only lasts 1-2 seasons. While I'm glad I'm not over-spending on clothing that generally never gets worn, the laundry, constant cycle of replacing, and lack of options sometimes gets me down. I'd like to get to that low-medium level.