You want a box that rolls well and that rotates/spins around on its wheels easily. Some guys prefer two fixed casters and two swivel, others prefer all four to swivel. I prefer 2 and 2.
Drawers, you want them to pull out easily and slide back in easily. I'm not overly bitchy about this, I have ball bearing slides on some and basic friction slides on others (on some my Kennedy boxes). As long as the slide goes in and out I'm good. I don't need soft close, I don't need it to lock in or out. I just need it to function.
Drawers. Slide one out and put the palm of your hand in the middle of the drawer bottom and press down. Steady? Clink clank clunk?
Drawer depth. This is important. Shallow drawers are fine, but you do want varying depths for what you'll store in them. If you already own socket trays, the socket holding geometry itself might define what drawer depth you need. If you don't have socket trays, then the drawer depth can define what type of tray you need.
I have several Kennedy rolling boxes that I've picked up on FB Marketplace or at auctions. They're great for me. I don't need shiny. But I do need functional. And being $100 for each stacked set of rolling boxes in the photo below? Me like. The one on its own wheels was in pretty good shape when I brought it home. The one on the furniture dolly came without wheels and must have been in standing water, it had some surface rust on the bottom. Cleaned that up and primed it. DUN. When I bring them home I take the drawers out, then take the slides out. I'll clean up the box, clean and relube the friction slides, then put them back together again. They'll be good for the rest of my lifetime.
Style-wise, there's nothing wrong with caring about what you care for, or wanting what you want because it's simply what you want. You want a shiny box get one. You want it to color coordinate with your car, get one that does. You just want one that works, then get one that simply works.
But you want sturdy. You want functionality. Still, give yourself some grace in the selection process. You think you need four boxes to hold your tools? Then get one. Load it up and use it. If you like it, then get three more. If you hate it, sell it, donate it, or put it in your basement and start again. Or just become eclectic with a mix and match set of boxes.
Good luck with your search.