When I was on a TV show recently and asked to name the one thing most women over 40 do wrong when it comes to fashion, I said underdressing — going for comfort at the expense of style. Funny, but when I’d been asked that same question in a pre-interview days earlier, my answer had been just the opposite: overdressing. Midlife women tend to get too glitzy and end up overdoing it, blinging out on all burners. Why, then, my about-face?
On a flight from New York to Chicago, I’d just encountered "airport dressing." At the terminals in New York and Chicago, I’d been surrounded by sloppy sweats in all shapes and sizes, hoodies, fleece pants with stripes down the sides, athletic sneakers that had never set foot in a gym — all accessorized with a big fanny pack. By contrast, the women in jeans and nice sweaters, or in pants and leather jackets with boots or flats, looked so powerful, so first-class to me.
Don’t get me wrong. Body-hugging velours are adorable — on tweens, or even on us when we’re home alone watching a DVD. And a supercool tracksuit like the one Madonna designed for H&M in 2004 works if you’re actually running to or from your trainer. But wearing oversized, shapeless sweatshirts is the same as not bothering to get dressed at all. If you look good, you’ll feel good. The desire for comfort is one we all share, but fulfilling it stylishly requires thought and strategy.
Department and specialty stores are packed with soft and slouchy feel-good clothing in a carnival of colors and weightless, wrinkle-free techno fabrics. Newer names in contemporary casual clothing are getting major shelf space. You’ve probably noticed Vince, Splendid, DKNY Pure, Velvet, Iisli, Michael Stars, Three Dots — and if you haven’t, get to know them. Personally, I’m not sold on the jumpsuit (too much work involved in every visit to the ladies’ room!), but here are some appropriate pieces to consider.
- Easy-fitting cotton knit sweaters
- Soft denim blazers
- Smock tees
- Knit cotton dresses in T-shirt fabric
- Layering tanks
- Drawstring or yoga-inspired pants
- Cropped pants
- Casual cotton pencil skirts
- Rubber-soled driving shoes
- Ballet flats
- Espadrille wedges
- Flat strappy sandals
- Flat boots
Look 1: What to Wear…
...for lunch with friends, mall crawls, or dinner and a movie
Layered knits are cozy but never sloppy — perfect for bridging the gap between relaxed and dressed-up. Layer Splendid’s cotton jersey dress ($133) over Tommy Bahama’s cotton tank ($38) for climate and decolletage control, then throw on a long cardigan by Gerard Darel ($218). Nine West wedges with patent-and-linen strap ($79). Ruehl Sophie hobo bag in oyster leather ($198).
Look 2: What to Wear…
...for coffee runs, walking the dog or even house hunting with your broker
A cropped trench, floppy pants, and silver glitter sneakers keep up the pace. AK Anne Klein’s water-resistant coated cotton jacket ($189) has enough structure and waist definition to handle it all, and Plenty by Tracy Reese linen-blend full-cut pants ($220) are as roomy as sweats but a thousand times chicer. Mimi & Coco cotton ribbed tank ($39). Converse for Target skimmers ($30) are pure weekend indulgence.
Look 3: What to Wear…
...for the book club meeting — or seeing your therapist, dermatologist, dentist, or lawyer