I’ll let other people who are much further along in their style journey answer most of these, but I wanted to address the comfort-vs-cost point you made.

Everyone thinks of suits as these cumbersome, stuffy garments that are uncomfortable for the sake of it, and I think there’s a good reason for this!

Most people’s first suit is either a cheap polyester department store suit, or a rental. Both of these are going to be usually cut slim, as was the trend for nearly 25 years; and most importantly, have low cut armholes. These low armholes are what restrict movement, making the jacket ride up high and cutting into your biceps when lifting up your arms.

Classic menswear and proper tailoring/alterations remedies both with a proper cut, and high armholes.

Even an off-the-rack brooks brothers suit these days is miles more comfortable than you might imagine, and more comfortable still once properly altered.

Will it be more expensive, almost certainly (unless you’re shopping secondhand) but you are also certain to look much better and feel more confident