I don't think you're ever too old to wear red. You'll want a foundation though that will neutralize the pink a bit in your skin so that the red won't emphasize it. Also you may benefit from trying reds in different formulas i.e. lipstick versus gloss versus liquid lipsticsk, etc. so you can find one that is comfortable on your lips and doesn't emphasize any lines.

You also don't need to wear the red color full on from the tube with liner, you could just tap it on with your finger for a stained look rather than super dramatic.

I'm not familiar with the Becca shades you mentioned, but the Hourglass is a true red with bluish undertones. I have fair skin, green eyes and blonde hair. I don't like coral-y reds (reds with an orange or yellow undertone) because I feel they make my teeth look yellow. The Hourglass red, with blue undertones, tends to make my teeth look whiter. (At least, to me they do!)

All day and does not bleed