Real SimpleFashion Director Victoria Sanchez-Lincoln tackles some of the questions we got when we put out this call on Facebook: If you could ask anything about style, what would it be?

By Real Simple
Updated October 29, 2013
Bob Hiemstra

Q: What’s on the horizon for skirt/dress lengths—are we over the maxi look yet? Also toe styles for shoes/boots: square, pointy, platform?

A: Square toes are out, and personally I hope they never come back! The shape is so blocky, it generally looks unflattering. Pointy toes are making a resurgence, though definitely not at the extreme lengths of a few years back. Of shoe-toe shapes, my favorite is the almond, a gentle oval that makes legs look long and lean. It’s also sophisticated, unlike an ultra-round toe, which can come off as young and even cartoonish. A pump with an almond toe is beautiful.

As for hemlines, pretty much anything goes. This spring look for everything from full circle skirts to flowy midis and maxis to flippy, flirty miniskirts. As always, the length or lengths best for you are really determined by your height (petite frames, for example, can get swallowed up by maxis), the aspect of your shape you wish to highlight (legs? waist?), and, of course, personal style. Two rules of thumb: When in doubt, go with a knee length, a timeless hemline. (For the most flattering effect, choose a skirt or dress that falls just above the kneecaps or just below them.) And avoid a hem that hits the fullest part of the calf, which will visually shorten and widen the leg.

Q: How can a beautiful, proportional, and very curvy plus size like myself wear leggings and/or skinny jeans without my legs looking like Christmas hams?

A: When picking leggings or skinnies, stick to dark tones: black, inky indigo, charcoal, even dark burgundies or teals. (Brighter colors will emphasize thighs; darker colors will slim.) For a flattering alternative to skinny jeans, look for slim or straight-leg cuts. Neither of these offers a skintight and leg-hugging fit. Instead, the silhouette is more columnar, falling in a straight line from thigh to ankle.

Up top, be playful with your choices, wearing brightly colored or embellished blouses and tees that will draw the eye. To visually lengthen your look, finish it with a cardigan or jacket—a tuxedo style is a great pick—that hits mid-thigh.

Q: I need help figuring out how to style all the ankle boots that are now out. Tuck skinny jeans in? Roll them?

A: Luckily, there’s no hard-and-fast rule. Really, this is more about what looks best on you and works with what you own.

Rolling your jeans and showing off a little skin between cuff and top of boot is a younger, hipper look. Note: The roll should be minimal, not chunky or wide, so for the best results try this with ankle-length skinny or slim-cut jeans. This look also works better with sleeker, more feminine boots, maybe with a stacked heel—nothing about it should look clunky.

Tucking your skinny jeans or leggings into boots can make you look taller and leaner because you’ll create one continuous line. But don’t stop there: Work the look with tights (opaque or sweater styles) worn with pencil or full circle skirts and flirty dresses. As for the boots, you have lots of latitude here: Wedges, western-inspired styles, Chelsea boots, even high heels all lend themselves beautifully.

Q: I love the fashionable necklaces these days, including statement necklaces, but I always struggle with earrings to wear with them. Don’t want anything too matchy-matchy or loud, but then what’s best—posts, hoops, dangly earrings? Or must we skip earrings in this case?

A: What it comes down to is this: Do your ears feel naked without earrings? If the answer is no, skip them knowing that your necklace will make a big enough statement.

But if you feel unfinished without earrings, simple studs are almost always the best choice. Look for a pair that coordinates in some way with your necklace, whether that means matching stones, colors, or metals (or all of the above). And be sure that you stick with the same style: No wearing a ladylike necklace with pyramid studs, for instance. Save them for something edgier.

The exception to the rule: If your dress is spare—a minimalistic LBD—feel free to go bolder with your earrings. Here, hoops or dangling numbers that complement your necklace would help bring focus and a bit of drama to your ensemble. But fair warning: Try this only with a restrained black dress. Florals, prints, and peplums have enough going on.

Q: I need to know today’s business casual. I see so much clothing that looks like either nightclub, golf club, or matronly. What is the stylish, classy professional wearing to the office these days? If you say jeans, I’ll scream.

A: Look for materials that are comfortable but have an inherently dressier feel (jersey, chiffon, cashmere). Try pairing, say, a flowy jersey top with relaxed trousers or—sorry!—nice jeans (if your work environment permits) for an outfit that toes the line between office-appropriate and easygoing polish. Chic accessories will make a big difference, too: Tying on a beautiful printed silk scarf will elevate virtually any outfit.