How to Wear Red Lipstick
To wear red lipstick, go with a true-red shade if you have fair skin, coral red if you have beige skin, or brick red if you have a medium skin tone. If you have olive skin, try a red with pink undertones, or go with a purple-red if you have a chocolate skin tone. For a coffee skin tone, try a cherry red to create a beautiful contrast. Whichever shade you choose, keep the rest of your makeup subtle, especially your eye makeup, so it's not overwhelming.
Pick a true red for fair skin. With doll-like porcelain skin, a true candy-apple red will add lovely color and contrast. Look for shades that have blue undertones (rather than yellow) to bring out a warmth in your skin tone. Try a coral-red for beige skin. Your skin is perfectly accentuated with reds that have a golden undertone and are coral-like. Rather than going super orange , find a red with very subtle pumpkin-y undertones. That will keep your lips looking sophisticated rather than costume-y. Go for brick red for medium skin. If your skin is slightly tanned, a bold brick red will create a classic look. Don't worry about going too deep; select a shade that is slightly darker and richer than cherry red. Pick a red with pink undertones for olive skin. Rich, copper skin is accented beautifully with a brighter berry red shade. The brightness of fuchsia and raspberry based reds compliments the natural warmth of your skin. Avoid looking too old or young by staying away from neon-bright berry reds. Go for a purple-red for chocolate skin. Deep chocolate skin paired with a purple-based red creates an incredibly chic look. Find a red in the same color as an ultra-ripe pomegranate or an under-ripe plum, preferably with a bit of gold iridescence or glitter. Try a cherry red for coffee skin. Skin the color of black coffee looks great with a bright red for the same reason that fair skin does: it creates a beautiful contrast. Find a glossy red with blue undertones. Consider a matte red. The most classic look available is a matte red lip. Matte lipsticks are the longest lasting and won't feather over time, making them ideal for a long day at work or a night out at a concert. Try a glossy red. For a more modern red look, try a glossy red lipstick. Unlike the sparkly red glosses of our pre-teen days, glossy reds are now made to add a sophisticated touch to your lips. Wear a glossy red lipstick as a stand-alone color, or layer it over a matte shade for extra long wear. Look into a stain. Lip stains are an up-and-coming in the world of makeup; they are a liquid lipstick/gloss hybrid that stains your lips with a matte finish for over 12 hours. On the downside, they can be difficult to remove. Consider a lip stain as an ultra-long wear alternative to a traditional lipstick. Try a red tinted moisturizer. If you're not quite ready to take the plunge into a full-on lipstick, test the waters by using a red tinted moisturizer. These hued balms have enough color to add the traditional rouge to your lips, but are easy to remove and slightly translucent. They tend to have a slightly glossy finish. Smooth out your lips. One unfortunate consequence of wearing red lipstick (especially matte lipstick) is that dry, peeling, and flaky lips are exaggerated. Use a sugar scrub to remove any dead skin from your lips, and follow up with your favorite moisturizer. Your lips will look significantly improved in red lipstick if they are smoothed and softened first. Outline your lips with a highlighter. To make your lips really pop, use a light concealer or highlighter and a small brush to apply around the outside of your lips. Gently blend the outer edge of the line for a more natural look. This will draw attention to your lips and create a greater contrast between the red of your lips and the natural tone of your skin. Add lip liner. Unlike lip liner of old, a nude or red shade will work to fill the grooves of your lips with a waxy coating, providing a totally smooth blank canvas for the lipstick. Draw on the outline of your lips, and then fill in the entirety of your lips with the liner. If you make a mistake, don't swipe it off with your finger––use makeup remover on a Q-tip (cotton bud) for best results. Slightly line outside your lips if you want your lips to look bigger. Consider using a reverse liner; it's clear and it allows you to outline your lips to prevent lipstick from running and bleeding. If you don't have a lip liner, pat concealer across your lips. Apply the lipstick. Apply a smooth, even coat of lipstick to the complete surface of your lips. You can apply it directly out of the tube, or use a lip brush for a more precise application. Make sure to pucker slightly so expose the soft center of your lips, an area often forgotten about. Remove any excess lipstick. You've likely seen women with lipstick on their teeth; definitely not an attractive look. Prevent this very thing by placing a tissue between your lips and pressing them together gently. Alternatively, place your index finger in your mouth and move it around gently. It'll lift excess red lipstick likely to smear on your teeth. Keep the rest of your makeup subtle. Red lipstick is a statement piece, almost an accessory. As such a bold statement, it is important to keep the rest of your makeup toned down. Heavy eye makeup with red lipstick will leave you looking childish or costume-like. Rather, keep a neutral eye with soft skin for the most classic look. Check your lipstick often. Unless you're using a top-of-the-line lipstick, it is likely that your lipstick will fade or feather over time. Avoid wearing bad lipstick for extended periods of time by checking it often. Wipe off any that has bled outside your lips, and even out your lips by wiping off areas that are particularly heavy. Reapply when necessary. Following the aforementioned tip, it is necessary to reapply red lipstick every few hours. When you noticed that it has faded significantly, swipe on a second (or third) coat. Keeping your lipstick fresh will keep your look sophisticated and classy rather than sloppy. Finished.  
Pick a true red for fair skin. Try a coral-red for beige skin. Go for brick red for medium skin. Pick a red with pink undertones for olive skin. Go for a purple-red for chocolate skin. Try a cherry red for coffee skin. Consider a matte red. Try a glossy red. Look into a stain. Try a red tinted moisturizer. Smooth out your lips. Outline your lips with a highlighter. Add lip liner. Apply the lipstick. Remove any excess lipstick. Keep the rest of your makeup subtle. Check your lipstick often. Reapply when necessary. Finished. 