Your clothing sounds very comparable to what I took to the Wind Rivers last August. I was on the "back side" of the Cirque of the Towers (Shadow Lake). It was about as close to heaven as I expect to get while on this earth!
As you are probably aware, you need to be prepared for severe thunderstorms, high winds, drenching rain, hail, sleet, snow. While I lucked out and had a beautiful week (but frosty nights), on my first day there was quite a bit of new snow evident fairly low on the mountains. I met two parties coming out who had hiked over Washakie Pass (comparable in elevation, I believe, to Jackass Pass) in a blizzard.
I would bring the base layer and gloves and substitute the balaclava for the beanie. You could substitute the synthetic T-shirt, if long-sleeved, for the top part of the base layer, or vice versa. Consider either lightweight rain mitts or a pair of plastic produce bags to put over the gloves to keep them dry in the rain. I'd also bring insulation with sleeves instead of a vest (Cocoon, Patagonia or Montbell UL Thermawrap). I never could stay warm in a vest. Your Mileage May Vary.
You need long sleeves and long pants because the sun is so fierce at those altitudes–sunscreen won't do the job. I notice you have my favorite sun hat! For that trip there are no deep river fords, unless you're going beyond the Cirque, so you could save a couple of ounces and annoyance with zippers by wearing plain long pants instead of convertibles.
The one thing I definitely would ditch is the windbreaker. First of all, it's way too heavy–you should be able to get one at half the weight. It is not essential, either because when it is windy in the high mountains, it's cold enough that your rain jacket is quite comfortable.
However, there were two warm, windless days in the Winds when I was vigorously attacked by horseflies, which regarded both my permethrin-sprayed hiking shirt and DEET as just so much appetizer. I really wanted that wind shirt for rest stops on those two days. It would have been too hot, but better than being chewed upon. Medieval armor would have been even better, but a trifle heavy.
Last year I found a Montbell windshirt (no hood), weighing 2.6 ounces, for half price at the Backcountry.com Outlet. Normally Montbell is very pricey. There are several other brands like GoLite, Marmot, Patagonia that make comparable windshirts. Look around at sales and closeouts–you should be able to find a windshirt at no more than 4-5 ounces that won't break the bank. A hooded one might be better for repelling the horseflies. Note that with Montbell clothing you want to get a size larger than you normally do–their clothing sizes run quite small.
Re shoes: many people hike in trail runners and use low gaiters to keep rocks, dirt, mud, etc. out of their shoes. I'm working on switching over from boots, but don't yet know if it will be successful. Great so far, with over a pound less to lift at each step. I need to get a 20-lb. pack out on some steep trails to be sure.
I hope that your weight loss was deliberate to lessen the effect of the diabetes! Many congratulations! As one who finds it very hard to keep the weight down, I hereby send you a virtual standing ovation!
Have a wonderful trip! The Wind Rivers are a really special place.
