10 Fashion Rules You Can Break

No long hair-or short skirts-after 40? No white after Labor Day? No, thank you! It's time to stop thinking of fashion in terms of the 10 Commandments, and start thinking in terms of the Golden Rule. As What Not to Wear's Stacy London puts it, "It's not about should I wear it, it's about, does it look flattering on me?" With that in mind, read on for expert advice on how to break fashion's outdated laws skillfully and make your look work for you. Because, says London, "for every rule about style, there's an exception."

RULE #1: Thou Shall Not Wear Red Lipstick by Day

For the last few decades, lips have been painted a subtle nude, and dramatic makeup has been saved for evening-even if nude lipstick makes you look like you've spent too long swimming in a frigid lake.

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You can wear red lipstick - or black eyeliner - by day. You just can't wear both at once. "Red lipstick is a wake-up for your face," says Falik. "It's a great way to distract from your eyes if you haven't gotten a good night's sleep." You just want to make sure that it doesn't look like it's been left on from the night before. "Keep the rest of your makeup minimal, so it doesn't look like you're dressed for an evening out," warns Falik. Similarly, if you favor defined eyeliner, keep your lipstick and other eye makeup more natural by day.

RULE #2: Thou Shall Not Have Long Hair After Age 40

Writer Dominique Browning set off a cyber-firestorm of comments when she wrote about having long locks at 55 in The New York Times, asking "why can't middle-aged women have long hair?" The only reason anyone could come up with is tradition. "It used to be, once you became a mother you'd have to do the June Cleaver," says Amy Tara Koch, a Chicago-based style expert and author of the style guide Bump it Up! "It just makes you look so old!"

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After 40 you absolutely can wear your hair long, or super short, or whatever style flatters your face. "The problem is when you date yourself with a style or a nonstyle, that actually ages you instead of making you look youthful," says London. So skip the inch-high hair-sprayed bangs you did in high school; instead, have your stylist layer your long locks into a face-framing shape that's past your shoulders (provided your hair is strong and lustrous). In fact, says Koch, long hair is sometimes even more flattering as we get older. "A lot of actresses use bangs to cover up wrinkles on their foreheads," she observes. "Look at Goldie Hawn."

RULE #3: Thou Shall Always Match Thy Shoes, Bag, and Belt

We've all heard it said by an authority figure, often one looking askance at our sandals: "You can always tell a lady by her coordinated, shoes, belt, and bag." While that was true once, says Koch, "That time is so over." Even Jackie Kennedy, who worked the matching hat-and-suit, shoes-and-bag rule to such success in the early '60s, abandoned the "coordinated set" look for sling-backs and totes large enough to carry the manuscripts she was editing once she was known as Jackie Onassis.

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"Matching your hat to your shoe to your bag, or your necklace to your earrings, has a tendency to look dated," says London. "Mixing up your accessories adds interest to an outfit, and can make you look much more modern and polished." Your accessories should complement your outfit, not carbon copy it. "If you're wearing a dress with a really bold print, then your bag and shoes should be solid," says Koch. Conversely, if you're wearing a neutral outfit, pick a shoe, bag, or shawl with a print. Look to accessories to modernize things you already have in your wardrobe.

RULE #4: Thou Shall Not Mix Black and Navy (or Black and Brown)

You know the theory: Pick one neutral and accent it with bright colors, because two basic colors will clash over which is dominant, resulting in your basic wardrobe power struggle. But in a post-Cold War age, can't we all just get along? Even our navy shift and black jacket?

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To get a little existentialist, when it comes to mixing black and navy (or brown), it's the intention behind the pairing that counts. What does that mean? "You want to wear them in a healthy dose of both colors, so it's clear you did it on purpose, not like you got dressed in the dark and wore brown shoes with an all-black outfit by accident," says London. Or, in the words of style expert and host of MSN's Beauty BFF Jenn Falik, "make sure everything has another anchor; if you're wearing black with one brown piece, throw in another one." A brown dress and shoes with black tights and a black belt would be ideal, for example.

RULE #5: Thou Shall Stay Out of the Sun

We all tell our dermatologist that little white lie: "I'm going on vacation, but I'll stay out of the sun." But we're not fooling anyone. And we just make it worse if we promise, "I always put on sunscreen right before I walk out the door."

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"Don't stay out of the sun, just protect your skin in the sun," advises New York dermatologist Neal Schultz. But don't do so by putting on sunscreen last. Instead, says Schultz, "you want sunscreen to be the first thing on your skin so that you're getting the SPF you've been promised." You see, the FDA tests sunscreens on bare - not moisturized or made-up skin. That's because chemical sunscreens need to react with skin in order to work. Sunscreens can be compromised if applied over moisturizer or other makeup. "It's like making your bed and realizing you left your pajamas under the sheets so they don't lie flat," says Schultz. "You won't get an even layer of sunscreen if there's something underneath."

RULE #6: As Thy Age Rises, Thy Hemlines Shall Fall

Once, a lady of a certain age showing leg would be called "mutton dressed as lamb." And nobody likes mutton. But the length of your skirt should be based on your comfort level, not that of the yackety-yaks around you.

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Hot pants are a no-no, but if you can rock a short skirt, do! "Look at Demi Moore and Sharon Stone," says Koch. "You can wear a shorter dress and a higher heel as you get older, but you want to make sure it's appropriate; you may want to layer it with a great sweater or a cool jacket," so that it's not short below and tight above, for example. Celebrity stylist Tara Swennen, who works with Angie Harmon and Gabrielle Union, says that when it comes to short skirts, "I recommend anywhere from three inches above the knee to right below the knee," an area that is considered the most flattering as it's the thinnest part of your leg (besides the ankle). "If you don't feel comfortable showing leg," says Swennen, "you can always pair a short skirt with opaque tights." Koch sometimes layers open-weave fishnets over opaque tights, working the style without risking overexposure.

RULE #7: Thou Shall Not Wear White After Labor Day

For generations, when September rolled around, white cardigans were wrapped with mothballs, and put away for a long winter's nap. But white goes with everything and can cast such a flattering glow on your face that it seems unfair to relegate it to one brief season.

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Two words: Winter White. You can wear white any time of year, from a chunky knit (or faux-ermine cape) in January to a sleek button-down come Spring. To play it safe, make sure the material you're wearing is seasonally appropriate. But even that isn't a hard and fast law, says London. "You could possibly wear a white linen dress in winter if you did it with black tights and boots and a leather jacket. There's always a way to mix and match things to create a mood that looks season-specific."

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RULE #8: Thou Shall Never Pair Open-Toe Shoes With Hosiery

In a dark corner of our brain we all have an image of an old man mowing the lawn in black socks and brown sandals; he is a cautionary tale, not a fashion inspiration. But sometimes we still want to wear our fabulous peep toes with our lovely charcoal tights.

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As with so many tricky styles, the elegance is in the execution. "You can wear tights with open-toed shoes, as long as there's no reinforced toe or even toe seam," says London. "You need to find tights so it looks like you're doing it deliberately, not like you forgot you were wearing open-toe shoes. It's about purpose and deliberation." And size does matter. "I would recommend keeping the shoe to a peep-toe," says Swennen. "I wouldn't suggest tights with a huge open toe sandal." Or a lawn mower.

RULE #9: Thou Shall Not Mix Metals

Another credo that belongs to a simpler, more stifling time and place specifies that when it comes to jewelry, gold goes with gold, silver with silver and bronze with bronze. But if this were true, then why does Cartier's trinity ring look so good?

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Blend your bling. "All metallics are neutrals," says London. "So it is absolutely fine to mix gold and silver, you just want it to look like it has purpose." To that end, Falik recommends, "keep it in odd numbers; if you're going to layer necklaces, do three; if you're doing a gold cuff with a silver, make sure you have an extra gold or silver, too, so it doesn't look like you're trying to balance." The uneven groupings create a more eclectic, modern style.

RULE #10: If It Doesn't Fit, You Must Acquit

You might love something, but if it doesn't fit right, put it right back on the rack. Such a tough rule when true love - of the shopping variety - is so hard to find.

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It's a question of flattery, not fit. The right fit is usually within your grasp - yours and a skillful tailor's. "Tailors are the most important thing in fashion," says Swennen. "Don't necessarily rule out something you love. Just know that you may need to tweak it to work for you." The only time to turn away from a look you love is if it doesn't look good on you even when the fit is perfect. "You have to respect your body type and make sure something is going to work with your shape," says Swennen. "I wouldn't wear a skinny jean, because it doesn't look great on me." When you do love what you see in the mirror, and it looks both appropriate and alluring, that's what you should be wearing, even if it's not the latest trend. "The key to personal style is understanding your individual beauty enough to know which looks will work for you and which probably won't," says London. In the end, confidence is the greatest accessory. And that's one style rule that will never be broken.

from Best You: Fit and Fabulous

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