Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Comfort shoes are ugly.

New Rule: With so many fashionable options out there, comfort no longer means frumpy. These triangle-heel sling-backs by former engineer and ballroom dancer Anyi Lu are not only sleek—they also have a cushy insole, a deep extended toe box and arch support. Cha-cha-cha!
$425; AnyiLu.com.
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: You have to pay a lot for designer looks.

New Rule: The latest designer collaborations give you a high-end look for considerably less. Check out these springy dresses from Milly for Kohl's and Lilly Pulitzer for Target (Gayle King was a big fan of the latter).
From left:
$51; Kohls.com.
$51; Target.com
.
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: You can't wear head-to-toe denim.

New Rule: You can wear denim without slipping into Texas tuxedo territory if you pair pieces with different washes—a chambray top and dark skinny jeans, for instance. Or you can hedge your bets with this Rag & Bone jacket: a dip-dyed denim number that's dark on top, bleached on the bottom.
Rag & Bone, $275; Barneys New York, 888-222-7639.
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Black is your go-to bag color.

New Rule: Brown is just as versatile, and it was all over the spring runways. Wear it the same way you'd wear black, and don't worry about matching your shoes. Tip: A rich luggage brown complements the most colors and is easiest to wear.
Ivanka Trump, $275; Nordstrom.com.
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: A diamond ring has to be a gift or mark a special occasion.

New Rule: You can absolutely buy a right-hand ring for yourself, no milestone necessary. I'm crazy for these distinctive diamond pavé and white gold rings by Gabriel & Co.
Starting at $2,100; GabrielNY.com.
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: White bottoms are only for summer.

New Rule: You can wear white year-round, and you definitely don't have to wait until Memorial Day. The important thing is to choose the proper fabrics and silhouettes. Go for textured materials and structured shapes, and avoid summery details like gauzy fabric or straps.
$119; AnnTaylor.com.
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Horizontal stripes make you look fat.

New Rule: There's no need to swear off stripes—as long as you find pieces that use them in flattering ways. This skirt breaks up the stripes with a zipper and tilts the pattern so it doesn't create a horizontal bar across your thighs.
$70; Express.com.
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Bra straps need to stay undercover.

New Rule: With so many beautiful options available now, it would be a shame to let your bra straps stay in hiding. Look for this season's sweet and sexy straps with details so pretty that any slippage looks stylish.
Clockwise from top left:
$73; Cosabella.com
Heidi Klum Intimates, $95; Bloomingdales.com
B.Temp'd, $39; WacoalAmerica.com
$40; for bra-and-panty set ($20 for your first set with code OPRAH20); AdoreMe.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Suede is only for winter.

New Rule: You can and should wear suede year-round! To keep the look summery, choose lighter colors (think muted pastels and brights) and warm-weather pieces like tanks, strappy heels or a fringed bag that's versatile enough to straddle seasons.
Shoe, $345; EtienneAigner.com
Bag, Mondrina, $460; HandbagDesigner101.com
Top, Lauren Ralph Lauren, $325; Bloomingdales.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Sparkle is only for evening.

New Rule: I'm a big believer in daytime shine, and on-trend statement way to wear it. These twinklers would elevate even jeans and a white tee.
Blue earrings, Elizabeth Cole, $338; ElizabethColeJewelry.com
Multicolored earrings, $50; RJGraziano.com
Green earrings, Akkad, $70; HSN.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Short women can't wear flares.

New Rule: Petite gals can wear everything their taller friends can—they just have to keep proportions in mind. To make your legs look longer, choose a higher waist. The pants should be tight and fitted to the knee. And look for a flare that's wide enough so you can hem the pant without ruining the silhouette.
$198; HudsonJeans.com.
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: All your jewelry should be the same metal.

New Rule: Matchy-matchy is boring-boring. Mix silver and gold for an effortlessly stylish look. Pair chunky pieces like this watch with delicate bling.
From top:
Bracelets, Maya J. $99 to $160; MayaJNYC.com
Watch, $395; CitizenWatch.com
Bracelet, $200; Miansai.com
Bracelets, Maya J,, $199 and $140; MayaJNYC.com
Bracelet, $75; Miansai.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Never wear shorts to the office.

New Rule: Shorts can succeed in creative workplaces, so long as they provide the same coverage as a pencil skirt. Add a blazer, and avoid beachy fabrics. Pair shorts with stacked heels or wedges—never stilettos.
Blazer, Lauren Ralph Lauren, $275; Bloomingdales.com
Blouse, $69; Talbots.com
Shorts, Risto, $430; NeimanMarcus.com
Bag, $550; ToryBurch.com
Shoes, White House Black Market, $125; WHBM.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Bikinis are the only sexy swimsuits.

New Rule: I've always believed that a one-piece can be just as flirty as a two piece, and now it seems designers agree with me. To keep the vibe sultry, not swim team, look for peekaboo details like the mesh and cutouts on this suit.
Mossimo, $40; Target.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Avoid miniskirts if you're over 30.

New Rule: It's taken a while, but I've finally loosened up on length. If you have the legs for a mini (especially if you're petite), go for it! Just make sure the length of the skirt is past your fingertips, and choose a sophisticated shape like the trumpet, soft flare or envelope styles shown here. To balance the shortness of the skirt, your top should be modest—no plunging necklines, please.
From top:
Parker,$253; ParkerNY.com
Nic + Zoe, $128; NicandZoe.com
$79; BananaRepublic.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: You have to match your shoes to your dress.

New Rule: Keep an open mind when it comes to color combos, even with trickier spring shades like yellow, navy and white. I've taken the liberty of showing you two shoe color choices: one a no-fail pairing and the other a bit more daring.
Dress, New York & Company, $70; NYandCompany.com
No Fail Shoe: Gold and brown are perfect partners for yellow.
Lauren Ralph Lauren, $165; RalphLauren.com
Daring Shoe: A bright orange heel is fresh and keeps it all in the (citrus) family.
$395; LKBennett.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: You have to match your shoes to your dress.

Dress, $350; RebeccaTaylor.com
No Fail Shoe: When in doubt, go metallic.
$275; Viaspiga.com
Daring Shoe: Forget the old never-pair-black-and-navy rule. The combo is chic and modern.
$139; VinceCamuto.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: You have to match your shoes to your dress.

Dress, KLS Kimora Lee Simmons; KLS.com
No Fail Shoe: Nude (never white!) shoes are a classic option.
$129; DuneLondon.com
Daring Shoe: A printed shoe is an instant game changer.
Ivanka Trump, $135; Nordstrom.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Shirtdresses are boring.

New Rule: Add an unexpected detail—like this obi-style belt— to give a classic shirtdress some edge.
Dress and belt, Serena & Lily, $325 and $68; SerenaandLily.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Running pants must be black.

New Rule: The freshest running gear is patterned, colorful and (surprise!) flattering. How is that possible? Each of these pieces has smart details that visually slim. Now if only they could make that 10K go by faster...
From left:
$79; Athleta.com
Xersion, $44; JCPenney.com
C9 by Champion, $25; Target.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: You can't wear boots in summer.

New Rule: Behold the summer bootie! Choose a pair in a lighter color and with a lower shaft height, and feel free to wear them with shorts, skirts or dresses. Bonus: Pick a closed-toe version and you can skip the pedicure.
Rag & Bone, $525; Rag-Bone.com
Fashion Rules You Don't Have to Follow Anymore

Photo: Jonathon Kambouris

Old School: Dressy occasions demand a dress.

New Rule: Want to stand out in a sea of long gowns? Go for matching separates, like this sleeveless tuxedo-style jumpsuit from H&M (left) or this printed Sachin & Babi number (right). Both options are absolute head turners.
Top and skirt, Sachin & Babi Noir, $350; and $595; SachinandBabi.com
Jumpsuit, H&M Conscious Exclusive Collection, $80; HM.com
Fashion Rules You Don't Have to Follow Anymore

Old School: A clutch isn't practical for daytime.

New Rule: Clutches can definitely work for day. Choose a streamlined style (like these from Aritzia) that you can carry or slip into your work tote.
Auxiliary for Aritzia, $250 each; Aritzia.com
Fashion Rules You Don't Have to Follow Anymore

Old School: Sunglasses should be neutral.

New Rule: Colorful shades can be just as flattering (and make your eyes pop without makeup!). To keep the look chic, go for frames in classic shapes—the color is the only twist you need.
From top:
$166; Lacoste.com
$175; ElieTahari.com
$136; Marchon.com
Fashion Rules You Don't Have to Follow Anymore

Old School: Mixing patterns and prints makes you look clownish.

New Rule: Mixing prints is a great idea—the look is unexpected and sophisticated. Just make sure the patterns are in the same color family or have a color in common. And the scale of the prints should be balanced: If you wear a larger print on top, wear a smaller pattern on the bottom, and vice versa.
Shirt, $13; OldNavy.com
Skirt, Nicole by Nicole Miller, $44; JCPenney.com