When it comes the mouth, the French have a rule - if the lipstick's red, the clothes are black.
This isn't a bad rule, actually. For daytime and less formal looks, a more natural pink or brownish mouth looks better than red, but dark clothing needs a brighter lip for balance. Whether you prefer a paler or a stronger mouth is up to you, but it helps to practise with several 'standard lips' that you can choose from without thinking, according to the season and what you're wearing. Try this procedure with regard to application:
If you want your mouth to look a bit poutier, outline your whole mouth with concealer/highlighter and blend it in. Something like Touche Eclat works very well. You can only pull this trick off, however, if you have little or no facial hair, as otherwise you give yourself a moustache. Do it properly, though, and your mouth will look a tad bigger, and it's a sure-fire way to prevent lipstick bleed.
Now outline your lips with lip pencil, following the contours of your actual lipline, NOT the colour line of the lips (which recedes as you get older). You can check your natural lipline by looking at yourself in three-quarter view in a mirror (again, this is a tip from Morgan Shick's Your Makeover). Then fill in your lips with the lipliner, like colouring in a drawing.
Lipliners come in different hardnesses and which you choose is a matter of preference, but don't have the point of the pencil too sharp - blunt it off for a soft, natural outline. I favour Yves Rocher, Maybelline and La Roche-Posay.
Using lipliner rather than lipstick gives a dense colour which won't budge or bleed into the cracks round your lips, but it's rather flat by itself, so it needs a top layer. So blot with a single layer of tissue, powder lightly if you wish (this is belt and braces to prevent lipstick bleed), then apply lipstick, if using, and/or gloss.
If you've used lipliner to fill in your lips, you may prefer not to use lipstick at all but move straight on to the final layer, gloss.
Lipsticks vary in colour and texture, but the over-40s are best-served by creamy lipsticks in gentle shades, avoiding mica, frosted looks and really zinging bright oranges and scarlets. Brownish reds often work better than scarlet.
Apply lipstick with a lip brush and work well into the creases in your lips, and take the colour right up to your lipline. For more staying power, blot and apply a second coat, but if you favour lipstick that lasts all day, try out one of the two-stage lippies such as Lipfinity by Max Factor. Personally I felt too made-up wearing this, and I hated the varnished feeling it gave my lips. My favourite lipsticks are by Revlon, but I can't get them here in France, so I wear Chanel or Gemey (French Maybelline).
Every woman looks good in lip gloss. Not the red vinyl porn-star type, of course, but the types which are not too shiny and which have quite a lot of pigment. These highly pigmented glosses tend to come in palettes rather than tubes, and often have a handy little brush with them - sometimes it's worth buying a complete makeup palette with eyeshadow, blusher and the rest, simply for the lip glosses. Apply this kind of gloss like a lipstick, taking them up to the lipline if you wish. If you have three main colours - red, pink and caramel - it's also a good opportunity to tweak your lip colours a little. I often apply pink over bronze, or caramel over pink for a subtlety of tone.
High-pigment glosses aren't always available, so if you can't find one and have to use the really sticky kind in a tube, you need a different method of application. Use just a tiny dot, press your lips together, then spread it outwards with a brush, stopping well short of the lipline, as otherwise it runs and gets messy. If it still appear too shiny, pat it with a finger until it tones down (some of it will come off in the process, along with your lippy).
With lips done, you're ready to leave the house without scaring the neighbourhood.