Oh wow. So many good things to think about! First, thank you all so much for the votes of confidence and for the thoughtful insight. So many of the things you've mentioned have started to set off light bulbs.
Some background. I'll be 50 in a couple weeks, and over the summer that really started to bother me. For the first time in my life, I had gained significant weight in my waist plus added a layer of insulation everywhere that hadn't been there before. I felt frumpy and old in everything I tried to squeeze into. My shape had completely changed, and nothing in my old wardrobe really suited this new shape. So late July/early August I decided to makeover my wardrobe and style as my 50th birthday present to myself. I ditched tons of stuff...it was way more like 20 items out to one item in. The things that were coming in were things that I felt better in...longer tops to wear out to cover the tummy, pants with a slightly higher rise, etc. So through the end of September, things were looking better, albeit fairly shapeless to camouflage the new shape.
Around then, my husband and I both had our annual physicals. Despite eating "right" and getting plenty of aerobic exercise, my blood pressure was up, and his blood sugar and cholesterol were up. After significant research, I did a complete about-face on our old way of healthy eating and exercising. Since October 2nd I've lost 10 inches, I have a waist again and my old pear-leaning shape has slimmed. Blood pressure is also fine.
So now, the higher waisted bottoms and longer covering tops are not what I want to wear. Don't get me wrong, I don't do tight/hoochee anything, but with the body shape change, I do want to acknowledge that I have a waist again, and I want to wear slimmer pants now that my pear half has gotten leaner. About 10 days ago on YLF was the first time I have ever worn skinny jeans (or boots over my jeans, for that matter), and I liked it. Who knew?
All is not lost, I just need to figure out how to reconfigure things. I have pants that I like but that aren't form fitting, so I need body con tops for those. I have slim pants that I love, and the looser tops will work for those. Although, I have to say that most of these are sweaters, and even though hot flashes were short lived about a year ago, I now just seem to run hot all the time.
Parsley, Caro, E...you guys really hit on this. Fit is elusive at the moment, and I need to figure this out.
Suz, your approach to wardrobe building is a much more clearly designed version of what I have been trying to do, although probably without enough up-front homework. My categories are:
Client meetings/showings. I'm in real estate, so showings can and most often do happen 7 days/week. I guess I'd call this a business casual look. I need to look finished and polished. This is my largest category because I want significantly fewer repeats here than I want in other categories. If it takes 4 months to sell a listing, I could conceivably see the same client 80-100 times in that 4 month period. Maintaining a larger rotation lessens the likelihood that the client will see the same outfit 20 times in a relatively short period of time.
Closings/open houses, agent caravans, listing appts. These tend to be dresses or skirts for me.
Work at home/errands/school volunteer. This is nice casual, but nice enough that if I run onto a client at the grocery store, I don't have to duck around the corner. Mainly jeans/cords and nice tops.
Morning carpool/evening lounge. After Gaylene gave me a much needed talking to a few weeks ago, my old stuff was tossed and replaced with my previous work at home/errands wardrobe that needed to be upgraded.
Gear. This category has also been upgraded, even though I work out at home.
Date night/social: I should have enough to pull from both home and client work wear. Cocktail dresses and holiday wear are separate.
Vacation. shorts, casual dresses, tee shirts
Well, I've written an epistle, and I've barely touched on the great points you have all made. I'm printing this now and will study it while standing in my closet tomorrow and evaluating what's working and why and what's not working and why not. I'll report back!