Last year I wrote a post on getting rid of legacy clothes–the lovely older bits and pieces we all hold onto hoping they’ll fit again some day. Last year I made some tough decisions and let go of almost all of them. I sold the size six leather pants (sigh!) and a cute J. Peterman crocheted cardigan and donated the rest.

So this January I’m tackling clothes that fit but just don’t flatter me. It’s been rather humbling. I liked them on the website model. I like them on the hanger in my closet. But as soon as I put them on and look in the mirror I shake my head and take them off. Others I have worn but have never felt confident in them.

Like many women of age, I have body parts I want to hide or minimize–like a squishy tummy and a too-generous bust. So trying to find items that fit and flatter, and that I like, is a struggle. I have a good handle on my colors (mostly fall) and what I like to wear so thankfully 75% of time I buy well, just fine, but that leaves 25% that items just don’t work. Twenty-five percent that end up gathering dust.

It’s time to let them go.

But it’s not easy. I think the biggest obstacle is the realization that “I paid a lot of money for this.” We’ve all been there. Paid good money for something that just doesn’t work. Of course one option is to sell those pieces (and I do on occasion), but regardless of how much I paid for something if it’s not being worn it’s not bringing any value to my life. Better to let someone else enjoy it.

The other sticking point for me is “I still like this.” Yup, I bought it because I liked it. But no matter how many times I try it on, it’s not going to look like it did on a 5’10” 125-pound model with B-cup boobs.

So I’m trying to be real with myself and let these things go. I decided to start small and fill one bag for charity.

First in the bag was an Eileen Fisher boxy wool flannel top in a rust color. It should have been ideal. I love the color. Loved the fabric. But I found the neckline and boxy style unflattering on me. And the few times I wore it (maybe four) I found myself trying to readjust the neckline. I wore it again last week and did not feel good. Okay time to go.

I loved the color and roomy fit of a velvet top I bought last year but it made me look 20 pounds heavier. Oh dear. I tried to convince myself it was okay and wore it a few times. But I felt self-conscious knowing I looked extra chubby in it.

I also included a vintage Ralph Lauren tweed jacket that I used to love wearing and it is cute as can be. It fits, sort of, though the days of being able to button it up are long gone so I stopped wearing it. Time to let it go.

One bag done. More to come.

In reality, whether I lose that 15 pounds or not, I’d rather have fewer clothes, but all items I love wearing and that I think look good on me. And I know it’s possible!

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