From chic cocktail parties to traditional family dinners—you have a slew of events on your social calendar this holiday season, and you have outfits for every occasion but have you figured out your lip look? Much like how you would not wear that revealing Hervé Leger number to the-never-ending dinner at your in-laws, lip gloss, stick and stain each have their own right time and place when it comes to the look, feel and lasting power they offer. Here’s a quick reference guide on what to wear (and we say branch out from your thought that red lipstick = holidays. Have fun!).

The family feast
When you’re sitting down for course after course, followed by a movie or chit chat in front of the fireplace with some eggnog, you want something that’ll be comfortable and that’ll last you the duration of the evening. Colour-wise, think subdued, soft and neutral — not an intense shade you would get from say, a red lipstick. “A tinted lip balm would be ideal,” says Toronto-based makeup artist Susana Hong. You get a hint of colour that’s soft, and it’ll last you through your evening of drinking and eating without transferring to your glass or holiday napkin much. “Plus, it keeps your lips moist, and you can just reapply easily, sans mirror, since precision is unnecessary!”

Try: Burt’s Bees Tinted Lip Balm in Hibiscus.

HOLIDAY BEAUTY: Get party prefect lashes

The “ugly sweater” party
When you’re sporting a bold and garish sweater, take a chance and be bold with your lip colour. “Why let the sweater be the only focus? Take a chance with your lip colour and keep with the holiday theme,” says Hong. A fuchsia or tomato tone will liven up your look, while standing out to go with the busy pattern of your knit number you’re sporting. Keep it from going garish but sticking to a creamy, moist lipstick.

Try: Nars Semi Matte Lipstick in Funny Face

A romantic dinner with your boyfriend
A candlelit, cozy dinner with your beau will surely involve some smooching, so the key here is to add some colour to your lips without it ending up all over him. Hong suggests a light, berry-toned stain. “He won’t even realize you have any lip colour on, and that’s the idea, isn’t it?” She recommends applying it to the bottom lip only and then quickly rubbing your lips together to deposit some of the stain pigment onto your upper lip. “This will de-saturate the intensity of the colour and keep the edges soft,” she explains. Do this quickly, though, as you only have a bit of time before the stain dries. If you find the particular stain you’re using leaves your lips feeling a bit parched, apply your favourite lip balm over top to moisten your lips.

Try: Revlon Just Bitten Lip Stain Balm in Beloved

GALLERY: 11 hot holiday hair ideas

The office holiday party is just the right time to bring out a red lipstick … find out how to do it on the next page!

The office holiday party

Normally, you have your everyday lip colour or two you’re comfortable with wearing to the office. But the annual holiday party gives you a chance to step outside of that zone. “After all, you want to look like you put a little more effort into your appearance than you normally do, and you want to look great in front of your peers,” says Hong. This is a great time to break out the
classic red lipstick if this is something you normally shy away from. If you’re not sure of what red lipstick will work on you, Hong says a bold cherry tone works on nearly anyone. Keep the lipstick velvety in texture—and there’s no need to be afraid a matte lipstick will dry out your lips (“The new formulas no longer feel extremely dry like they once did, plus they generally stay put, and transfer minimally,” she says). Feel free to skip lip liner, too (Hong suggests using liner only if you feel the need to enhance the structure of your lip shape).

Try: Lancome L’Absolue Rouge in Caprice

IFT IDEAS: The prettiest holiday stocking stuffers

Night on the town

You’ve broken out the
sequins and high heels for a festive evening of cocktails and fun times with your besties. And a night out translates to going as glitzy as you want—which means, when it comes to lips, all signs point to lip gloss. “Loads of shine and shimmer all in one tube. And so many come with heavy pigmentation, so the days of layering your gloss on top of your lipstick are over!” says Hong. Bonus: Pick a gloss with a mirror right on the tube, so reapplication is simple (and regular reapplication indeed is a must with lip gloss to maintain the high shine), not to mention you’ll have even more room in your clutch).

Try: Smashbox Limitless Long Wear Lip Gloss in Boundless