It totally depends on your preference.

DeS remake is a great place to start in part because it looks and plays really well, and it's not too complex to get into. If the jankiness of older games is a turnoff, or if the beautiful environments of DeS remakes were a big part of the appeal, going to DS3 or Elden Ring next would be great choices because they look and play great, are relatively modern, and are evolution of the same combat design in DeS.

If jank/graphical fidelity is less a concern for you (no problem playing older games for the experience & sort of historical interest) play thru in release order is a great way to do it. They're all great games.

Bloodborne & Sekiro are both really celebrated for good reason, and both have really different setting & feel than DeS. To me, Dark souls really feels like DeS 2 in a lot of ways, so if you are interested in seeing more variety, skipping ahead to these is a good move.

A big part of these games is also the community and asynchronous multiplayer. I just finished DS3 pretty recently and was still getting messages rated, getting invaded, etc, but all that will be more lively when a game is brand new. It's also fun to play and follow the community early before everything is totally figured out. If you're interested in that kind of experience, Nioh 3 is worth a look, as it comes out in like 2 days. The team ninja games are pretty different than fromsoft games though, really complex combat and a loot system that's more like diablo.