Hi Cora --
Lucky you to have some closet orphans you love and feel right to you!
I've been where you are but didn't have a clear sense of where I wanted to go, so I did more of the "smooth transition" thing for a few years.
For you, though, I'd suggest dividing your budget so that you do both the dramatic *and* smooth. I have friends whose budget allowed for the "dramatic" and it is a little fairy-tale like...and it'd be great if you could have some of that feeling with your new clothes.
So: for the "D" side I'd make sure every new purchase was building toward creating outfits with other new items or the orphans. It means being super-analytical for now, and saving impulse buys for later.
I'd make sure your new "love it" or "just what I need to go with 'love it'" items were:
* current season/for your next few months of weather
* in a color range, texture, and "right" silhouette for other new or beloved items
* ones that worked with the clothing (if shoes/accessories)
If that means starting with ONE bottom, 1 top, and a pair of shoes/scarf/jewelry so be it -- just make sure the next top/bottom/accessory works with what you have.
[I actually ended up with what I call an accidental capsule one winter by following this without thinking it through, and now try to create create mini-capsules when it's a season where I buy 5-6 pieces. With 2 bottoms and 3-4 tops you can get a fair amount of flexibility. It's really just the travel capsule idea...minus the travel, ha.]
The above can take time so I'd also be ruthless about buying items that are bridge ones to your non-favs.
Ideally for the "T" you'd make sure the new items were flexible enough to wear with multiple things, but if it's a "this top is cheap, I can live with it, and it works well with Closet Item I'd love to donate down the line" moment then that's reality.
IME people tend to notice tops more than bottoms so you can get away with a lot more repetition there than you might think. [There have been many years where I rotated 2 pairs of pants and 1 skirt during a 5-day work week....]
Good luck and keep us posted!