The 50 Best Fashion Tips of All Time

Take a classic cue from Marilyn Monroe! They elevate jeans and keep ball skirts from drifting into fantasy-land. But all that mileage comes at a cost: a short shelf life. So buy three, don't overbleach (which can cause yellowing), and refresh regularly.

Take a cue from Jackie O, who had a closet full of sheath dresses. If you find an especially flattering fit right off the rack, go ahead and buy doubles. When it works, why question it?

"The biggest mistake women make is wearing pants that aren't the right length for their shoes," says stylist Kate Young. To fix this, hem to either heels or flats like Emmanuelle Chriqui-no going back. Generally, hems should just graze the tops of your shoes and be from 1/2 inch to 3/4 inch off the floor.

"Once you know which silhouettes flatter you, filter trends ruthlessly," says designer Shoshanna Gruss. For instance, if you're petite and shapely, it's best to avoid tall columns and billowy maxis even if you love them. Go for a dress with a defined waist and just-above-the-knee hem.

Coco Chanel's more-is-more approach still makes a statement today. You can do multiples of the same material, or better yet, go for contrast: Try a femme piece with edgy chains, feathers with beads, or pearls with diamantés.

A great-fitting dress or pair of pants from a line one season may mean similar success the next, as shown by Pippa Middleton. Designers, especially higher-end ones, tend to size their clothes based on a regular fit model.

Keep in mind: White clothes always look more see-through in daylight. Check yourself out in a bright setting to be safe, like Jennifer Hudson must have done.

"Outerwear should never be an afterthought," says Holmes amp Yang co-designer Jeanne Yang. "So many people only see you in your coat—if you're not wearing something great underneath your trench, they'll never even know!" Look for a stylish coat, like Twiggy's here.

Combining colors, scale, and patterns in a way that looks dynamic takes practice, but there are some basic tricks to getting it right. You can wear two prints that repeat the same colors or mix a large-scale pattern with a smaller one. What's even easier is to use the second motif as an accent (like Zoe Saldana in Vionnet, left).

If your evening dress is a stark stunner (or has a lot of embellishment), one single showstopping accessory, like Grace Kelly's earrings, is all you need.

Nothing comes back the same way, and the jumpsuit of 2011 is not necessarily the same as a version from the '70s. Check out the difference in Raquel Welch's and Katie Holmes's jumpsuits. There are subtle design tweaks that make any revival slightly different from the original. Does that piece from your "archive" really work now? Ask a trusted friend for a second opinion.

It will pull you in a bit (so long, spillover!) and also help even out your proportions. Take a note from Kim Kardashian, left.

Don a pantsuit a la Bianca Jagger and you'll immediately stand up straighter. Anna Johnson, author of Savvy Chic, says "a waistcoat, a crisp pin-striped shirt, or a really big watch or cravat telegraphs power." Don't forget to balance it out with lipstick and taller shoes.

Whether it's grosgrain with sequins, a motorcycle jacket over a formal gown, an oversize choker with an easy white T, or a vivid belt like Gisele Bundchen's, a touch of contrast makes good outfits great.

Few mortals can pull off head-to-toe baggy. So take a cue from Lauren Conrad and team your billowing pieces with something body-conscious. (Hint: This is what leggings were made for.)

Simpler shapes cry out for styling. Try dressy jackets or a slip-on shrug, colored shoes and bags like Abbie Cornish, or tinted sheers plus booties.

You want to be comfy, sure, but also chic enough to be tapped for an upgrade. A sharp blazer and scarf or a lightweight cashmere wrap is the unofficial uniform of jet-setters worldwide, as shown by Elizabeth Hurley. To complete the outfit, just throw on jeans or leggings, then add flats, heels, or riding boots.

On trousers, the distance between the crotch and the waistband is critical to the fit. It's also not something that's easily altered, so make sure pants are neither too snug nor droopy in this area before you buy them. Rose Byrne shows off the perfect fit.

Arms svelte enough for a sleeveless sheath? Legs toned enough for shorts? Take a note from Julianne Moore and show off what you've got-while you've still got it.

49. ...But Watch Out for the Matronly Tipping Point
The pleated silk skirt or little pastel jacket that looked so cute on you at 25 can start turning frumpy at 40.