Knowing what I know now, I would've told my 20ish self to buy a ready to wear navy suit and a made to measure three piece dinner suit and call it a day. A pair of clean black oxfords, a couple quality white dress shirts, a couple of ties, a real bow tie, and a white linen handkerchief would complete the look. All of this now would set you back about $5,000 to $7000, but that's all you would need to get you through most things in life for a few decades — a job interview, formal events, weddings, parties, and networking gigs. Add a dark grey suit maybe if wanting options.
Of course I didn't do that and splurged on several suits and jackets from my amazing tailor Thomas Mahon, at least I hope he's still my tailor since I haven't ordered anything from him for quite some time. He's also cut suits for King Charles, Jony Ive, etc. oh, and me.
You go by cloth and some of the clothmakers he's used for me are Dormeuil, Harrisons, Smith Woollens, and Hardy Minnis.
My favorite suiting is the Fresco line from Hardy Minnis and I had a dark blue suit and a mid-gray suit made. Fresco has a bit of a rough, open weave texture, matte look and finish, that doesn't wrinkle, and it's a great suiting for warmer climates. I had both made up in a half lining and apparently Tom made the same suit gray suit for himself.
Before the Fresco suits though, we went with Cape Kid and did a navy suit, a dark grey suit, and a stand out blue odd jacket. The Cape Kid line is composed of 60% mohair aka Angora goat with the rest wool which makes the cloth have an interesting shiny effect. I didn't think that was true until I saw pictures. Effectively, I have a shiny/fancy set of suits, a matte/low key set of suits, and a pair of work horse Fall/Winter suits. Go back to the first paragraph, since all of this was too much, but a really fun experience and I learned a lot. Cut/fit, cloth, and details plus years of apprenticeship, tradition, experience, and craftsmanship make for some really cool suits.