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Sylvia is a classic. Cassidy is dated to the mid 90s to the early 00s.

Sylvia

While Sylvia is a classic, cassidy is an aged trend, making it the dated option.

Sylvia was in vogue longer ago, more than once, and didn't completely drop off the map when fashions changed.

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Cassidy's popularity was more flash in the pan, so it feels more dated (i.e. pertaining to a specific era). Cassidy has a wild west flare, but I think it needs 20 years before it returns.

Cassidy.

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Cassidy reminds me of babbling brooks, short curly hair, trenchcoats. A kind of Twin Peaks vibe?

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Sylvia feels verdant and a bit melancholy, quite motherly.

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I prefer Sylvia.

I've never met or, locally, heard of a Cassidy. It seems to be pretty exclusively American. Sylvia has been used for so long that there isn't one single way of imagining a Sylvia. I like it and would consider using it IRL.

Sylvia is pretty timeless, it's far more ancient. Cassidy is more specifically dated to the 70s or 80s. Cassidy is also more exclusively American (as a first name), whereas Sylvia and its variants are used in multiple cultures.

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I prefer Sylvia.

Cassidy, definitely. Sylvia's a timeless beauty.

Cassidy is more dated because it was only popular for a short time and those tend to date much more than other names. Sylvia is old-fashioned, but it was popular for a lot longer than Cassidy and now might be getting more use.

Sylvia to me is more dated, I prefer Cassidy

to me Cassidy. Sylvia, like most greco-roman names, is timeless to me.