Adam Glassman

Our style expert
O's creative director and style expert Adam Glassman breaks down this summer's most flattering trends and shows you how to wear them well.

You have to take them seriously, not just throw on an old, schlumpy pair. Someone with great legs may get away with midthigh length, but slightly above the knee looks better on most people. I prefer a reasonably full cut (we're not talking billowy) that skims the thighs and camouflages sensitive areas. My usual caveats apply: no low-riders, no skintight fit, no bunchy pleats. Actually, I've been shocked lately by how chic shorts can be—in the office or for evening.

Above: Silk taffeta shorts. (Cynthia Steffe, $195), glam up with a beaded top (Bamford, $1,295) and jeweled sandals (Patricia Green).

Long Dresses
I am loving the maxidress this summer. It's loose, cool, stylish—and you don't need to fret about whether or not your legs will survive public scrutiny. Don't pick anything too gauzy, or it will look weird on dry land; an opaque jersey or cotton is good. And it shouldn't be oversize: Balance the skirt's length and volume with a fairly-fitted, not-too-bare bodice so you feel properly dressed. This is a terrific choice for hosting a party or going to one (with jeweled slides and lots of bracelets or beads), but you could also throw it on for running around town (just add a slouchy bag and flip-flops or flats).

Above: Prints are hot, and a bold florah (Tocca, $385) is a sweet way to test the waters (try a smaller pattern if you're petite). I think two colors are much easier to wear than a whole bunch.
White jeans

White Jeans
White jeans freshen up anything you wear, from a navy blazer and striped tee to an embellished tunic top or bright twinset. They also tend to feel a bit dressier than blue jeans. As for the fear factor, if light-colored pants fit well, they will not make your butt and hips seem bigger. As you may know, I prefer bootcuts or straight legs, not extreme skinnies, with added stretch for comfort. And so what if they show the dirt sooner than dark denim? Just toss them in the machine (you might even invest in dry-cleaning for an ultrapressed dress-whites look).

Above: Jeans clean up nicely when white five-pockets (Fidelity Denim, $168) team with an embroidered blouse (Irving & Fine, $375). Touches of color come from a diamond-motif belt (Boss Orange) and beaded sandals (Patricia Green).
red raincoat

Bright Rain Gear
My motto, like the post office's, is that you must deliver no matter how stormy the weather—you can't let your clothes or psyche be dragged down by a soggy day. Even if you're not normally into brights, color helps lesson the gloom: a great red, a taxicab yellow. Be practical about the fabrics—don't wear something flimsy that will get soaked immediately or become see-through when wet. We're lucky that patent leather is so popular these days; the shiny surface not only resists moisture but lifts your spirits. Get a good trench (at least one) in khaki or black. If you live somewhere particularly rainy, you might want a few to choose from. Boot up smartly instead of ruining your outfit with crummy sneakers. And a fun umbrella is essential.

Above: Jacket, Y-3, $509.
frye boots

Cowboy Boots
Don't wear them, even with jeans or long Western skirts, unless you're vacationing at a dude ranch or auditioning for Oklahoma! Cowboy boots originally functioned to fend off sagebrush and rattlesnakes, but most ladies no longer need that kind of protection. I was a cowboy boot addict in the '80s, so I know there's nothing more comfortable than a broken-in-pair that molds to your feet. They're also fantastic as an art form. But unless you're trying for an urban cowgirl look, they're probably too costumey for real life. A hipper choice is the newly revived Frye boot ( In a season of chunky substantial footgear, it fits right in.

Above: Frye Boots ($248) are today's cool version of cowboy boots. They've been around since 1863, but I think they still look modern because they're simpler, more rugged, and a lot more comfortable (no pointy toes).

Floaty Empire-Waist Tops
It's terrible to hear "When are you due" if there's no baby on the way. Billowy blouses invite that because they magnify the problem area; same goes for the opposite extreme—stretchy, tummy hugging tees. You need tops that are shaped but not tight. Other smart strategies:
  • Upper-body enhancers like cap sleeves, open or vee necklines.
  • Shorter hems on fitted tops—just to the base of the stomach. You might think a longer top hides all, but (sorry to be so graphic) you'll look like a snake that's just swallowed its prey.
  • Curvy tops or jackets that flare out under a nipped waist.
  • Buttonless or wrap styles (shirts and cardigans are tricky because buttons may gap over your abdomen).
    The right pants are crucial, too: Try a slimming pair of Lee Jeans' Instantly Slims You jeans or trousers with a supportive mesh front panel.

    Above: The long tie draws the eye down and away from the midsection. (Dana Buchman, $275)
Yellow bag

The Medium-Sized Weekend Bag
The pieces I find appealing are natural and bit rough-hewn: matte leather or suede rather than polished calf or patent leather; brown of cognac rather than black; silver hardware, not shiny gold. I also think strong, interesting textures—straw, canvas, wood—are great. While you're at it, ease up on your body. Give that giant, shoulder-stressing carryall the weekend off and switch to a soft, lightweight medium-size bag. And dump the pumps in favor or smart flats like driving shoes, ballerinas, and cool sneakers (there are hundreds now).

Above: Leave the laptop at home and pick a nice, squishy bag (Mulberry) that holds just enough.
Black shirt and gold skirt

Summer Blacks
Black is a universal, multiseason color; in warmer months it just needs to feel lighter. My suggestions:
  • Pick airy, diaphanous fabrics—voile, eyelet lace, chiffon.
  • Avoid high collars and long sleeves or you'll look like a Sicilian widow. Better: a breezy shift dress.
  • Relax with accessories in natural textures like raffia, wood, and leather.
  • Try a graphic combination of black and white or khaki—I love, love, love this look.

    Above: A black shirt (Thomas Pink) gets a lift from a khaki skirt (Lauren by Ralph Lauren), woven purse (Hobo International), cuffs (R.J. Graziano and Ben Amun), and zebra-print shoes (Anne Klein).