re: Need to cull my wardrobe. Tips?

Are you talking good quality brand name shirts, or random button up shirts from Walmart or Tractor Supply?

For good quality basic staples, no need to throw them out unless they have features that are out of style (like collars from last century to give an example that was already posted). If you have too many, just keep the ones you like that fit well.

Anything you're unsure of, if you're married ask your wife. It's in our job description to make sure y'all look presentable when y'all leave the house.

For new stuff, I'd suggest somewhere with a large selection like Macy's. Go during a slow time and if the salesperson seems chill, ask for recommendations based on what you like. I did that with my husband a few months ago, and it was actually kinda fun (like most men, he hates clothes shopping). That nice lady was running all over the department trying to help us find shirts he might like. He got a few nice shirts, some slightly outside of his comfort zone, that he gets compliments on when he wears.

As for t-shits, I just did a big purge of mine a few weeks ago. Anything old but sentimental, I cut out the design and put it in a box that I keep in the attic. Sure, the kids will have to throw it out someday, but one more box for the dump isn't going to kill them. I don't feel like I'm throwing away memories, and they're no longer taking up prime closet/ drawer real estate. But that's a chick thing that I wouldn't expect a baw to do. My husband uses his rejects to wear during messy projects or for shop rags.