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Roundwounds that sound more like flats

All my basses except a couple have Labella flats. The only rounds I use are DR Nickel LoRiders, and I let 'em get nice and old. They can totally get thumpy. Fingerstyle, live, I'm totally fine using these in situations I'd normally use flats. Pickstyle with any amount of treble is of course where you're gonna have a harder time getting there with any round, the envelope of the note and the type of attack are so different. Clunk vs clank.
 
Everything I was going to suggest has already been suggested so I’ll just agree with some that have already been listed:

GHS Pressure Wound (or Ken Smith Compressors - same string, different gauges available). These feel a lot like smooth rounds and sound somewhere between rounds and flats. When they go dead they sound similar to flats and the tension is similar.

GHS Balanced Nickel. They sound similar to flats once they die. They’re more flexible than most flats sets.

GHS Boomers. They start out bright but they die quickly and then last a really long time. I’m not sure I’d say they sound quite like flats once they’ve died but they’re definitely tubby.

I respectfully disagree that D’Addario XLs will ever sound like flats, even when they’ve gone dead. It’s not a bad sound but it still sounds like rounds - maybe like rounds under a pillow.

I would start with the Compression Wound, personally.
 
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I respectfully disagree with all the above, having played all the above. For a round-wound set of strings that takes on the character of flats, meaning all that woody, organic, goodness reminiscent of Fender VC Squier Company-made flats from the golden age, the strings to use are GHS Balanced Pure Nickel. They live up to their name in all ways. As they seat in, they lose the zing and take on that woody organic goodness we all miss with original Fender flats. Yes, as with all rounds, you gotta give them some time to settle in. But once they do, oh, my! On my 30-inch travel bass with a Nordy Mustang pickup, I can get the 1969 Bill Wyman tone of his Mustang with flats in spades.
Do you prefer the GHS pure nickel as 40 or 44 gauge?