Lipstick - what should one do?

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Find a colour which suits skin tone, hair etc and stick to it? Or vary lippy according to outfit, time of day, occassion?

Opinions please as I am venturing out of my comfort zone plummy colour (have worn or years) and have invested in a much more noticable pretty intense dark pink and a red.

I thank you

I wear lip gloss rather than lippy tbh

It depends on outfit and eye make up. I do like a barely there eye with a strong lip . Or a smokey eye and a nude lip

I have had my colours done with House of Colour and the advice was that you need 3 lipsticks! So I have 3 which tone with the colours in my palette, one of which goes with my reds, one with my corals and another which goes with everything else. I also have a coral pink lip gloss and a 'natural' lipstick to wear when a no make up look is called for. Very easy. I just buy the lipsticks from House of Colour by mail order. No 'mistakes' and a good price too as if you are a House of Coulour client you get a 30% discount. And no, I don't work for them - just an evangelical convert.

I have lots and vary constantly. Must say I am a make-up junkie but at a minimum:

clear gloss
cherry/plummy tinted gloss - noticeable but quite sheer and not an intense colour
'nude' lipstick usually pinky-brown
strong red (optional but instantly glam...)
strong plum or brown