Carter, I SO hear you on clearing out your dad's things. So very hard. I am avoiding that very issue with my mother's stuff. It hurts and it is hard, but it must be done. It's totally understandable if you need to take breaks while doing it.
Meanwhile, you are ROCKING the August challenge like nobody's business. You really have taken charge of your closets in an incredible way. I think you deserve some kind of YLF award for most achieve. One year sees your entire working closet revamped and revitalizes, and the next sees all the chaff go flying out on the summer breeze.
As Angie says, your "uniform" works, so no need to fix it. Also, a hi-lo hem on that dress will make it killer.
I SO remember those oversized 80s jackets. I should get out a few photos of myself from back in the day. We really did wear things too big. I remember I used to wear model "sample size" 10s from the Scandinavian designers stocked by the retail store where I worked. (Marimekko, Vuokko). At no time in those years could I have been a true size 10. True, vanity sizing hadn't come in yet. But at most I would have been a 4 or 6. (I only hit a size 10 just before my big weight loss a few years ago.) Still, I bought and wore those clothes and thought they were brilliant on me. Ridiculous!!
I've done pretty well on my own August challenge. My goals were to create a workable travel capsule (done -- it worked). And to try out some more Angie ensembles that I had backlogged -- and I have. I still have a few more to try out in real life, but once I do, I'll post them either individually or as a series.
Thanks for the inspiration!!