It takes time to get used to how it looks with a red/bright/darker lipstick than usual. So you might feel that it looks strange when you just put it on, but after a while, you should get used to how it looks.
Instead of going for a full red mouth, how about starting with a stain? It's still red, but not as much in-your-face as a classic red lip.
Also, if you need to use a lip liner, either use one in the same colour as the lipstick or a clear one. I personally don't think it works with a pink one, nor does a nude one look right.
I always match my blush colour to the colour of my lipstick. You can even use the lipstick as a blush by applying it in thin layers with your fingers.
Depending on your skin tone, consider a warm toned red instead of the blue toned like Ruby Woo.
You can also go darker or lighter. I personally love Tom Ford's Black Orchid lipstick (I'm fair with warm undertones, medium blond hair, blue eyes). Revlon Fire & Ice is nice too - used as a stain, it looks coral on me, while used as a classic lipstick, it's a bright red.
I have MAC Absolute Power and Ronnie Red, which are similar to Ruby Woo, but less matte (and Ronnie Red is brighter). They are nice, no doubt, but they are very drying (which I find with all MAC lipsticks), to the point of my lips being very flaky. Also, they leave a very pink stain on my lips and after a couple of hours, the lipstick looks pink on me, not red.
A neutral red might be better for you - such as MAC Russian Red.