My Fave Everyday Fall Dress for the Over-40 Woman

Relaxed, Versatile, and Chic: Lilly Pulitzer Skipper Dress

In the winter, I struggle to find clothes that are stylish, easy to wear, flattering, cozy, AND age-appropriate. As ya’ll know, I am not a fan of pants, so I tend to prefer a sweater dress, but my pear-shaped body limits my options.

I stumbled upon the perfect solution: a comfy dress that can be thrown on quickly, but gives the illusion of looking very put-together if styled correctly. Not too short nor too clingy, it’s a viable option for many over-40 women looking for an informal fall/winter/spring dress that can be worn on numerous occasions: running errands, shopping, school activities, brunch with friends, or casual Friday.

I shop at Lilly Pulitzer ALL THE TIME. I’m on a first name basis with almost everyone there! The Lilly ladies at the Austin Domain are the BEST!

I had noticed a new dress style, but assumed it wouldn’t work on me. Since I was already at the store, though, I tried the heather grey Skipper Popover Dress on a whim. I quickly realized that it was a perfect alternative to a sweater dress!

Niki Taylor exemplifies stylish girl-next-door

The fabric is essentially similar to a quality sweatshirt material. It has a little extra room in the hips/thighs and the fabric doesn’t cling, making it very flattering for someone who is pear-shaped. On the other hand, it’s not cut like a sack, so it would be flattering on other body types, too. A lot of sweater-style dresses are cut too tight or too loose for my frame. This one has a shape without being tight. I bought the medium because I needed the extra room through the hips/thighs.

I love how much the zipper changes the overall look! Of course I am small-chested, so I don’t have an issue with cleavage. For those who do, though, the zipper gives you flexibility on how much cleavage you would like to show. In fact, you can zip it all the way up!

Furthermore, it is MUCH more versatile than you would think. I had my wedges on, the zipper down fairly low, and the sleeves slightly pushed up. It had an ease, but styled to look a little sexier and not too preppy.

I prefer the heather grey, but this is pretty close to how I would style it (with different shoes); I’m only 5'4" so it hits a couple inches above my knees

There was another woman about my age trying on some things. When she saw me in it, she immediately wanted to try it too. Her style was TOTALLY different than mine. She was definitely funkier than me with a disheveled long bob and groovy booties. She wore it zipped up all the way with the booties. She had an edgy fashionista vibe combined with a tailored feel (channeling a relaxed Tilda Swinton vibe). After seeing the other woman, I realize now that you can wear a cool black boot to style it in a much edgier manner.

The white sleeve against the heather grey makes a beautiful detail. Sadly, photos don’t seem to capture how striking that particular combo is in person. It can go feminine if styled a certain way or look almost architectural if zipped up all the way.

The white detail is even more distinct in person!

The skipper dress is available in other solids and a few prints, but the heather grey gives the least preppy feel compared to the other color combinations. I plan to pull out my beautiful soft grey boots to wear with it on colder days, but throw on my wedges for the “shoulder” fall and spring season here in Austin.

A final styling option is obvious: ultra-preppy. Have it monogrammed and/or wear it with your aqua, lavender, or hot pink accessories to channel the most conservative look.

Extra scoop: small kangaroo-style pockets and machine-washable (though I recommend air-drying)!

The only down-side to the Skipper Popover Dress might be the price at $158. I will wear it so much in the warmer Austin climate and I have such a difficult time finding this type of dress that works on my body type, I am willing to overlook the price point. Cozy, comfy, versatile, AND stylish is something I’m always on the look-out for!

Even when you need something casual and practical: you deserve better than average, boring, and schlubby!

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