
If you think you're "too" something—old, fat, short, shy—to try the new fall clothes, think again. O's creative director, Adam Glassman, is here to talk you through fashion blocks so you can get the most of the latest trends.
1. Can I risk jersey on a body that's not perfect?
2. I'm 5'5" and a size 10. Can I wear wide-legged pants?
3. Can I mix prints without looking like a clown?
4. Can a 40-something get away with looking a little "downtown" or "arty"?
5. Can I wear my summer dresses in the fall?
6. Can I dress sexy without being inappropriate?
7. Can I wear bright colors and not look like a golden girl?
8. Can I wear brooches without looking like a news anchor?
9. Can I wear denim for work or evening and not feel underdressed?
1. Can I risk jersey on a body that's not perfect?
2. I'm 5'5" and a size 10. Can I wear wide-legged pants?
3. Can I mix prints without looking like a clown?
4. Can a 40-something get away with looking a little "downtown" or "arty"?
5. Can I wear my summer dresses in the fall?
6. Can I dress sexy without being inappropriate?
7. Can I wear bright colors and not look like a golden girl?
8. Can I wear brooches without looking like a news anchor?
9. Can I wear denim for work or evening and not feel underdressed?

More structured than slinky: Wrinkle-free double-knit wool suits yoga instructor Val Dorfman Allen, 50.
Jacket, skirt, and shirt, all Charles Nolan. Necklace, M.C.L. by Matthew Campbell Laurenza. Clutch, Nancy Gonzalez. Tights, Wolford. Shoes, Manolo Blahnik.

This go-to day dress in wool jersey (Diane von Furstenberg) has a cowl neckline that draws the focus up, downplaying curvy thighs like those of actress Michelle Griffin, 30s.
Ring, Megan Odabash. Bracelets, Ippolita and Ten Thousand Things. Tights, Spanx. Boots, Cole Haan.
Smoothing the way: See 4 undergarments that will make you look sleek in jersey!

Color continuity—gray all the way—gives a vertical slant to restaurant manager Denise Dalfo, 55, and her wider trousers (Diane von Furstenberg).
Shirt, Charles Nolan. Earrings, Irene Neuwirth. Clutch, Mulberry. Ring, Marco Bicego. Shoes, Christian Louboutin.
Going Wide: A Buying Guide
- A substantial waistband helps define your midsection so you don't look tubular.
- Solid colors minimize hips, making everything seem longer.
- Smooth, drapey fabrics (gabardine, jersey, wool crepe) don't bind or cling.
- The fullness should start at the knee. You don't want baggy.
- Pleats bulk you up—skip them (or at least pick the inverted or stitched-down kind).

Start here: "I told Carrie Clores, 39, a working mother, that plaid trousers will never live their best life if they hang out only with solid colors (Peter Som sweater and pants)."
Earrings, Elizabeth Showers. Shoes, GF Ferre.

Earrings, Genevieve Jones. Shoes, Tory Burch.

Next: Soften your palette with a mélange-knit cardigan (Richard Grand). The accessories (belt, Hobo International; shoes, C'N'C Costume National) remain simple.
Earrings, Alexa Sidaris for Covet Jewellery. In hand: Shoes, Delman.

Finally: Pile on brights (for advanced practitioners only). The scarf is tonally connected to the other pieces (M Missoni); the yellow bag (Cole Haan) is a calculated risk.
Shoes, Sergio Rossi.
Mastering the Mix
- Different patterns are compatible only when colors are the same (or closely related).
- Menswear motifs—plaids, checks, stripes—function almost like solids, so prints often look good with them.
- Variations in scale are interesting. A smaller print with a medium one looks fresher than two of equal size.
- Patterned accessories are a lower-risk proposition if you're concerned about getting in over your head with bigger pieces.

Fine details—nailhead-studded boots (Stuart Weitzman) and a fringed nickel-coated brass necklace (Burberry Prorsum) add personality to the basic black dress (Zero + Maria Cornejo) worn by Regina Mumme Whitaker, 49, a mother of two.
Scarf, Zero + Maria Cornejo. Tights, Hue.

Shoes, Christian Louboutin for L'Wren Scott.

September: Entertainment television host Chantal Bolivar, who is in her 30s, can save money by wearing cable-knit tights (DKNY) with open-toe shoes from summer (Halston).
Cuff, Ewa Solarska.

October: The dress acts like a skirt under a long pullover (Tibi), accented with a belt (Linea Pelle Collection), and python ankle boots (Fratelli Rossetti).
Earrings, Ted Muehling. Brooch, Fabrice. Tights, Wolford.

November: Now you need a real coat (Charles Nolan), knee-high boots (Michel Perry), a scarf (Yarnz), and gloves (Burberry).
Belt, Linea Pelle Collection. Tights, Wolford.

Before: "Repeat after me: I am not a Real Housewife of Orange County. This dress is too short, skimpy, and glitzy. Big hair and obvious makeup make matters worse. You want a natural, freshly washed look."

After: Photographer Kristen Jensen, 45, proves that nothing is sexier than a slightly unbuttoned white shirt (Tevrow + Chase); a pencil skirt (J.Crew) always outclasses any mini. Shine is fine if it's neutral silver (sequined jacket, Gryphon New York).
Belt, Hyde Collection. Shoes, Jimmy Choo.

Before: "The Bumble-Bee Effect is what results from a "just add black" approach to wearing color. Orange + black = The Great Pumpkin. Red + black = Superhero Syndrome. I could go on...."

After: Under a warm brown coat, a burnt-orange dress positively glows (both, Halston)—and so does Regina in her face-flattering new haircut. Tights and shoes (Wolford; Halston) are in tonally relevant ginger.
Necklace, Pono by Joan Goodman. Belt, Linea Pelle Collection.

Pin down a turtleneck or cowl-neck to bring color and shine closer to the face.
Jeweled flower, Alex and Ani. Logo brooch, Chanel. Green flower, Rachel Leigh. Sweater, Adam.

With busy patterns, wear one important, oversize piece (then go crazy with bracelets).
Brooch, Miriam Haskell. Bracelets, M.C.L. by Matthew Campbell Laurenza. Jacket, Thakoon.

Nature-based designs have their roots in Art Nouveau—stunning against this dark green dress.
Brooches, Fabrice. Dress, Marni

Romance a cami or wrap up a cardigan with sparkly antique-style pieces.
Brooches, from top: Blue Tree; Kenneth Jay Lane; Erickson Beamon; Robert Rose. Necklace, Gerard Yosca. Sweater, J.Crew. Camisole, Josie Natori.