I don't really have to shop anymore. Don't get me wrong, I still buy clothes whenever I need them, but I don't have to go out on expeditions any more or just browse for that thing I didn't know I needed until I saw it. Over the last few years, I've learned a lot about my style, my preferences, and what works for my lifestyle and I know from past experience will actually get worn.
I keep a running list of what I'm looking for at any point in time. When I see something that fits the bill, is high quality, and a good price, I just get it. Unlike most other things in my life, I don't feel guilt about it.
Example: before I was pregnant, I had a pair of black Paige jeans, which were a pretty useful wardrobe staple. These jeans were great and super comfy, but they had ankle zips (lesson learned: don't buy pants with ankle zips, it limits the type of shoes you can wear with them). I sold those (lesson learned: if you buy good quality, you can usually get some money back when you get rid of them), and kept my eye out for another pair. While I was looking, and while my body adjusted to having created a human, I wore a cheap pair of black jeans from Old Navy that served a transitional purpose. I decided that this summer, at the Nordstrom anniversary sale, I'd see if I could finally replace that pair of black denim. I tried on a few pairs, the AGs were amazing, on sale for a good price, and the decision had already been made. Easy.
The other day, I had a few minutes in between appointments and stopped in at The Vault. I tried on a bunch of things and found a few that had been on my list to be replaced. Since they were resale, it was great quality stuff for Gap prices. The things that worked, I bought. Took 30 minutes, tops.
I'm certainly not saying that I have it all figured out. I still buy things that I don't need or things that don't hold up as well as I hoped they would (looking at you, Banana Republic cardigan). However, I honestly feel a lot less anxiety around whether I'm making the right decisions when shopping. If only I could find a way to get that feeling about the non-clothes-related decisions in my life!
So, to keep myself accountable, these are the other things currently on my list: a cool bag that fits my laptop, grey cardigan, lightweight casual fall jacket, and Birkenstocks to replace current ones (hoping to find them on end-of-summer sale). Anything else will have to be super-special to even be considered.
Apparently, this works for my clients too. I sent out an email to all my clients this month, reminding them to book time for the fall. I got several responses to the effect of this one from Diana: "You taught me so well (how to know my style, weed out my closet, go shopping for one item at a time and with a list made ahead of time) that you might have taught your way out of job with me! I learned so much from having you as my personal shopper. Thanks to you, I feel confident in my clothes and am able to go shopping when I need to." and Persis: "I've learned something about which of my habits are abiding preferences, so the trip we did together was a very important step in the right direction." and Joanne: "The time that we spent with you last spring still influences how we shop, dress, etc. As we clean out our closets and shop for new items, we think about how you helped us and the advice that you gave us. I think that your sense of style, wardrobe planning skills, and the encouragement to get rid of what we're not regularly wearing have influenced us the most. I still don't like shopping, but working with you has helped me to put together outfits for myself with less stress."
The whole process is more than a one-time reboot, it's a constant learning process.