The right shade of lipstick can make the difference between your makeup job looking classy and elegant, or tacky and tasteless. You should always consider your skin tone when choosing a lipstick, as this is the canvas upon which your lipstick choice will be displayed. Selecting a lipstick color that works well with your skin tone and isn't too jarring is the best way to enhance your natural beauty.
Women who have pale skin with blue undertones look best in cool colors, like rose, coral or peach. Those with golden skin tones should lean toward warmer lipstick shades, from a pale caramel to a rich russet. Darker skin tones are enhanced with brighter colors as well as tawny shades, like raspberry, or a brandy colored lipstick.
When dressing for a specific occasion, it is essential to not always match your lipstick to your outfit. As with jewelry, sometimes less is more; too much of one color can make it appear like you're trying too hard. Makeup should make a woman look beautiful - just not in a 'painted-on' way. It should look like it is a part of her face, and should show off her features rather than overshadow them. Only when wearing solid black or white is it permissible to wear whatever color strikes your fancy.
When wearing shades like blue or purple, lipstick colors in varying shades of rose are best, as they bring out the natural flush of a woman's cheeks. Green and brown clothing calls for an emphasis on more earthy hues, like honey, cinnamon and chocolate. These colors also look lovely on women with olive skin tones. Yellow and orange shades are bright enough, so a lip stain in a nude or pale tawny color looks best rather than a darker, creamier lipstick; for example, you could consider lip stain in shades of champagne or butterscotch. You may also choose to wear a clear, shiny lip gloss.
Lipstick should also match well with the rest of your makeup for any particular day. Dark, smoky eye shadow is best matched with a cooler lip color like a pale pink, or a nude shade. A less dramatic eye can be paired with a sultry red lipstick, and so on. Metallics should be used on only one feature; either lips or eyes, but not both.
A note on jewelry: Silver jewelry goes best with cooler skin or clothing tones, and gold jewelry looks best on warmer tones. Neutral shades are exactly that, and can go with both. A lavender eye and a rosebud lip are wonderful with a pearl necklace or silver chandeliers; whereas gold hoops are set off to perfection with bronze and cider shades.