I used to dress terribly. When I had kids, I basically gave up on looking good and took “athleisure” a little too seriously. I wore a uniform of a Patagonia jacket,  black t-shirt, and black jeans. I didn’t look terrible, but I didn’t look particularly good either. I never put any effort into my appearance and as a result I noticed my self-esteem started to slip. A couple years ago, I did something that sounds ridiculously expensive, but isn’t. I hired a personal stylist. Basically, I sent her a bunch of photos of me, then each quarter she’d send me a whole bunch of outfits and tell me how and when to wear them. Over time, I graduated to the point where I felt confident choosing my own outfits and started buying my own clothes again. But I noticed something. I’d get into clothing ruts. I end up wearing the same sorts of outfits, or sometimes I’d get stuck. What kind of shirt goes with khakis again? The other day, I tried something. I uploaded a photo of the outfit I was wearing to ChatGPT and asked: “Help me make this outfit better.” It filled the screen with ideas. “Try wearing it with a pair of brown desert boots, a stainless steel watch, and a pair of black sunglasses, with your hair a bit more casual.” Suddenly, my outfit was upgraded. My girlfriend even noticed. For the last week, I’ve been doing this every day. I’ll throw on a pair of pants or something and start asking for suggestions to go with specific outfits, or feedback on color combos—something I’ve always struggled with. Who knew we all had a personal stylist in our pockets? So cool!