Despite being something that everyone does literally every day, getting dressed (or putting together an outfit, if you want to get fancy), can feel like the trickiest, most frustrating part of the morning. Who hasn’t stood in front of a closet full of clothing and thought “I have nothing to wear!?” Rest assured, you’re not alone in this daily conundrum. To that end, we consulted a panel of experts—top designers, style consultants, and retail pros—to demystify the act (art?) of getting dressed, once and for all.
How to actually do it: Obviously, you want to show off what you’re proud of—toned arms or a slim waist. It’s the downplaying of less beloved parts that’s tricky. One tactic? Add opposite volume, like wearing wide-leg trousers to offset a heavier upper half that’s wearing something fitted. “The object is to even yourself out,” explains designer Nicole Miller. “So avoid anything too oversize or you’ll look bigger.” Another idea: Distraction. If you’re pear shaped, wear forgettable black pants, then bring the focus upward with a bold scarf, says Louise Roe, the author of the style-advice book Front Roe.
How to actually do it: Odds are, there’s a grown-up version of the style du jour. Take crop tops: To avoid revealing skin, pair a shirt that hits at the navel with a high-waisted skirt—or a longer top with a crop top over it. “It gives you a similar look,” promises designer Rebecca Minkoff. Bottom line: “You never want to seem like you’re uncomfortable with your age and trying to look younger,” says Lilliana Vazquez, a style expert and the editor of TheLVGuide.com.
How to actually do it: “Where your breasts sit on your chest makes a big difference in how clothes fit,” says Vazquez. In other words, if you’re wearing a bra that fits properly, there will be no sagging or bulging—and that means your silhouette will look trimmer from every angle. The target is midway between your elbows and shoulders. You’ve scored a match when “the front center panel of the bra lays flat, there’s no wrinkling or gapping in the cups, and the bra is not hiking up or creating bulges,” says Kristen Supulski, the director of merchandising for Vanity Fair Brands lingerie. “If you can squeeze just two fingers under the band and it still feels snug, that’s the perfect fit.”
How to actually do it: Strive to wear colors that enhance one another rather than “match” in the traditional sense. For an easy hack, says Minkoff, “look at a simple color wheel. The colors that are opposite each other on the wheel complement each other.” (Think non-obvious but fetching combos, like orange and navy or purple and saffron.) Diversifying your accessories, in both color and texture, is another do. (A beloved trio from the vault of Betty Halbreich, a personal shopper at New York City’s Bergdorf Goodman and the author of the style memoir I’ll Drink to That: “A black dress, navy shoes, and a burgundy handbag.”) And under no circumstances should you ever rock a suite of jewelry. Says Vazquez, ” Anything that was sold together as a set looks really dated.”
How to actually do it: “Don’t give people too many things to look at all at once,” says Halbreich. “If you’re wearing a low-cut dress, focus on the cleavage—you don’t also need bare arms and legs.” The concept applies to fit as well: A body-hugging dress is better with a more sensible neckline and hem, whereas a skirt that hits a few inches above the knee won’t raise eyebrows if it’s flared rather than tight.
How to actually do it: First, a disclaimer. There’s no need to break the bank on the basics—tees, button-downs, jeans—of which there are plenty of quality options available at low prices. Instead, splurge (if you can) on the types of items in which even the cheapo versions aren’t exactly steals. For instance, bargain cashmere will still set you back $100. But that sweater will stretch out quickly, and then you’ll have to blow another $100 to replace it, rather than spending a little more only once. “When buying classics, like a great black blazer, it’s important to invest in better fabrics— say, wool—that will hold up better over time,” says Minkoff. Try calculating the price per wear to help stave off sticker shock.
How to actually do it: “Figure out your go-to, foolproof looks,” says designer Nanette Lepore, then seek out variations on that theme. Stumped? Picture the outfits that you feel most comfortable in. Or ask people close to you what you look best in. Once you’ve zeroed in on what works, find different takes. “I gravitate toward jackets, so I’ll do a bomber style, then a silk version, or a denim jacket with leather sleeves,” says Minkoff. “Whenever you feel the need to talk yourself into things, that’s a red flag that you shouldn’t buy them,” says Minkoff. If you have doubts in the dressing room, it may help to take a photo of yourself in the item, suggests Aerin Lauder, the founder and creative director of the lifestyle brand Aerin. “It’s much more accurate than looking in the mirror.”
How to actually do it: Opt for a pure white, rather than ivory, which may skew dingy. “But since white has the potential to make your teeth look yellow in comparison, consider wearing a bold lipstick with a blue undertone, like fuchsia, so teeth appear brighter,” recommends Florence Thomas, the creative director for Thomas Pink. Not sure which cut is best for you? A button-up with darting at the waist or curved princess seams can create a feminine hourglass shape on anyone. Be sure the seams of the shoulders line up with your shoulders and that there is no pulling across the front or the back. “Anything else can be tailored,” says Thomas. To keep all-cotton shirts from discoloring, don’t dry-clean them. Have them laundered and pressed, the same as men’s shirts.
How to actually do it: Doubling up on patterns can help you come across as confident and chic—or as if you got dressed in the dark. Achieve the former by following these guidelines. Stick to a similar color family—and preferably the same background shade. Some pairings are like PB & J—they just work. “Polka dots with stripes or florals typically go well together,” says Minkoff. The same holds for leopard print with a non-critter pattern or paisley with squares or checks. Near matches are a no-no. For example, says Vazquez, houndstooth and plaid are too similar to be simpatico. And two large-scale prints will compete for dominance—and give people a headache. Finish off the outfit with neutral accessories. Cautions Roe: “Don’t add another color into the mix.”
How to actually do it: The right pair of earrings can flatter your face shape. For instance, long earrings make your face look skinnier, if it’s on the round side, says jewelry designer Lizzie Fortunato. On the other hand, if you have an oblong face, short, chunky earrings, like oversize studs, will draw focus outward, and your face won’t read quite as narrow. If you have a large bust, a necklace should hit an inch above the cleavage or higher. Longer strands or pendants will rest awkwardly on the body and call attention to every contour. Lastly, choose earrings in lighter colors, such as pearls or white stone, to make your face look radiant.