I decided to do something about my clothes situation in a kind of maniac retail therapy moment. Some googling and convivence to a place I had to be otherwise lead me to Bonobos. Bonobos is a particular style of business casual menswear, basics with a slimmer and softer silhouette, and what seems to be a reasonable compromise in quality between dropshipped trash and $3000 bespoke nonsense (link to Arrested Development clip). You can check out their offerings on your own, but they have solid base layers of pants and shirts that range from 'yay, tan' to 'THAT is an interesting shade of purple'
The actual process was way more painless than I remember clothes buying being. The clerk was incredibly friendly, sized me up at a glance, and then knocked his estimations down a size to get the right fit. The cool part is that Bonobos is all electronically integrated. They get your size, set up a profile, and then they ship the clothes to your house and they just fit. There's enough care in making sure everything is true fitting that you can go to their website, hit the 'my fit' tab, and add whatever looks good to your cart.
While unfortunately I don't have photos, the tl;dr is that my clothes have always been on the baggy side for dumb Reasons that no longer apply (being a growing boy, loose 00s style, bodyshame), and having lost 20 lbs recently, my baggy clothes went to positively tentlike. Dressed right I have a waist, I have an ass, and I look good.
So I went a little ham on last season's going out of stock sale, but I'm set. And I'm now locked in to not regaining those 20 lbs.