In fashion, the rules are often meant to be broken—which just makes the perfect outfit even harder to find. To relieve the stress of getting dressed, three style experts are offering their guidelines for those "what am I going to wear?" occasions.
Joe Zee, creative director of Elle magazine, says you can never go wrong with a little black dress. "You don't want to be caught in a situation where you don't know if you're dressy enough," he says. "A simple black dress is always sophisticated enough but not overdressy." Pair it with a red shoe, and Zee says you've got a fail-safe holiday outfit.
If jeans are more your thing, Adam Glassman, creative director of O, The Oprah Magazine, suggests pairing a great pair of denim with a modern take on the holiday sweater. "The anti-Christmas sweater," Glassman says. Nix the bells and Santa for beautifully embellished, sequined and beaded sweaters and cardigans.
New Year's Eve Cocktail Party
"New Year's Eve is a time to break rules," says Mary Alice Stephenson, celebrity stylist and contributor to Harper's Bazaar. "It's a time to play with makeup, give yourself a great red lip, have fun with a big, bold eye. If you can't have fun with fashion on New Year's Eve, when can you?"
If you're usually uncomfortable baring your legs in a short dress, one of this season's biggest style statements might be your best friend. "A pair of tights can change everything," Stephenson says. "You can really learn to love your legs in a great pair of stockings or tights."
A casual summer affair should evoke an easy, breezy "I just threw this on" vibe. So why is it so hard to pull off? Instead of spending the afternoon worrying if you're showing too much skin, Stephenson says a maxi dress is the perfect, easy summer dress. "There are so many great easy summer dresses to throw on," she says.
As for your footwear, Zee has a sleeker alternative to the flip-flop. "This is the time to pull out a ballet flat," he says.
Sometimes, it's just better to stick to the classics. Zee says a conservative black suit still makes a great first impression. "Go for something more classic, more simple," he says. "You don't want the person interviewing you to be staring at your outfit the entire time. You want to look polished."
Once you've got the job, add your new suit to the "one time only" section in the back of your closet. To give a classic suit jacket or blazer an update, Stephenson says to add a great skinny belt to cinch in your waste. If you don't have one, velvet ribbon will work just as well. "It costs nothing, and bows are really big this season. And it shows off your waist," she says.
Your first instinct may be to get completely dolled up, but Zee says to stay away from the 6-inch stilettos. "I think guys like girls who are a little bit more down-to-earth," he says. "You don't want to spend your first date thinking: 'Oh god, my feet hurt. I can't walk anywhere.'"
"Black tie" used to mean floor-length gown. Now, the line is much grayer. "I think it's okay to wear cocktail-length to a black-tie wedding," Zee says. "It's about being body-appropriate. If you're shorter, a long dress is just drowning."
For grand affairs that still require a long evening dress, Stephenson suggests altering the dress after you've worn it. "Don't be afraid to get it chopped off at the knee and wear it another way," she says. "If you're going to buy a dress, you want to wear it more than once."