By Cindy Weber-Cleary
Updated Sep 10, 2014 @ 11:18 am
Credit: Danielle Oberrauch/

InStyle’s Fashion Director Cindy Weber Cleary has been a fashion editor for the past 20+ years. Needless to say, she’s picked up some tricks along the way. Catch her column each week for how-to tips and style secrets on her favorite, timeless styles. We gave readers the chance to ask Cindy style questions on Facebook. Here, Cindy responds to one lucky reader. Head over to our Facebook page and a submit an idea for Cindy’s next column!

Q. “Would love to see styles for the over 50 ladies for fall!! Classic but not frumpy … we love leather but want ideas that look classy combined with fresh new ideas!” —Denise Welch Stites

A. Thank you, Denise! There is absolutely no reason a woman over 50 shouldn’t wear leather unless, of course, she is vegan, in which case there is some very good, realistic faux-leather these days. I have a number of leather items in my closet that I get a lot of wear out of: a single-breasted coat, a knee-length pencil skirt, a vest with fur trim, as well as a sheath dress and cardigan jacket with leather trim.

I am happy to report that there will be plenty of ladylike leather to shop for this fall. For women our age, the key is to stay away from anything too biker-ish (motorcycle jackets, studded leather, for example) too short, or too tight.


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If black leather still feels too rock ’n roll for your comfort, try a softer neutral such as olive, blue, wine or taupe.

Get the look (from left): Massimo Dutti, $380,; Zara, $279,; Vince, $495,


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Whether pencil-shaped, A-line, or pleated, the skirt should hit around the knee or slightly below.

Get the look (from left): Bailey 44, $328,; Tibi, $1,000,; Joseph, $1,495,


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Leather pants are a bit trickier. I would advise you to stay away from leggings and skinny cigarette pants unless you wear them with a tunic top, a hip-length jacket or sweater. There are some new, easier to wear shapes such as a highwaisted trouser, a tapered trouser or a loose track pant.

Get the look (from left): Rag & Bone, $1,195,; DKNY, $255,; Zara, $60,

Classic Shapes

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Look for classic shapes that don’t show too much skin: a sleeveless dress with a demure hemline, a menswear-style topper or feminine blouse all get a little edge when translated into leather.

Get the look (from left): Zara, $149,; The Row, $3,290,; Barneys New York, $1,295,

Partial leather

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Last but not least, you can ease into wearing the trend by choosing items with leather sleeves, trim or insets mixed with another fabric. You will not only look chic and modern but you will also pay less than you would for a piece completely made of leather!

Get the look (from left): Mackage, $595,; Rebecca Taylor, $525,; Rag & Bone, $595,

Runway inspiration at top (from left): Hermes; Derek Lam; Chloe.