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8 Outfits Women Over 40 Will and Won’t Wear

We consistently turn to women over 40 for much of our sartorial direction. After all, we consider this set to be certified experts given their time developing polished personal wardrobes after style trial and error over the years.

While we recently highlighted the jeans women over 40 love, we thought we’d focus next on the specific ensembles some of the coolest women over 40 gravitate toward in their day-to-day. After all, who better to nab a little outfit inspiration from than those with that primo fashion knowledge?

And to dig even deeper into the matter, we thought you’d also be interested in the looks these women don’t really wear anymore to add to that outfit inspo journey. Of course, age really has nothing to do with what you should and shouldn’t wear—but hey, there might be something worth taking note of with the style advice coming your way. 

With all that said, keep scrolling to check out the outfits five women over 40 will and won’t wear for work, the weekend, and going out. Plus, shop staples throughout that will work for anyone at any age. And also note that the quotes coming your way are based on personal preference from the women featured—you should always wear whatever you personally love and what makes you feel comfortable and confident. 

“I stay away from tight suits and tight white shirts when putting together an outfit for work. Instead, one of my favorite outfits for work is a midi dress and knee-high boots, or an oversize blazer with a white shirt, tapered trousers, and unique heels.” — Renata Jazdzyk

“I have never worn a fitted knee-length dress to work. Ever. Instead, this is about as scrubbed up as I get with velvet dungarees, a smart shirt with a good collar, and a cute cord blazer layered under a statement coat. I am lucky. I work in fashion. I can pretty much wear anything to the office. In fact, I could probably go to work in an incy-wincy teeny-weeny yellow polka-dot bikini with a fluorescent green welly on my head and nobody would bat an eyelid. ‘There goes Tray,’ they would say. ‘She works in the fashion department…’ ‘Oh that explains it then…’” — Tracey Lea Sayer

“On weekends, my go-to outfit used to be jeans, a sweatshirt, and sneakers. It took a minute to break this habit. I realized that I could be cute and casual. Now I put more effort into my weekend looks.” — Georgette Niles

“When we often think about casual weekend outfits, we think tracksuits. I love to incorporate some sport elements into my outfits. However, I stay away from full sporty looks—especially tight tracksuits. My go-to formula for a casual outfit includes oversize jeans, a white T-shirt, and an oversize cardigan or blazer. Comfy and easy. To make my casual outfit a bit more unique, I love adding statement jewelry like a big necklace.” — Jazdzyk

“One area of my wardrobe that has definitely improved is my casual game. In my 20s, I didn’t give much thought to my look on a casual day. It was a jean and whatever T-shirt I threw on. Now I love casual separates so much—especially soft sweatshirts, sweatpants, and sweaters. A pair of distressed jeans and my favorite T-shirt and cardigan are a current go-to of mine.” — Jeniese Hosey

“For a night out, I find that I don’t like to wear hemlines that hit above the knee anymore. I now gravitate to a longer silhouette because they make me feel more put-together and sexier with minimal effort. As for outfit formulas, lately, my go-to is a slim, black turtleneck. I pair it with (or without) a blazer, then add jeans and boots for a polished yet casual look. And for a night out, I like to wear it with something a little edgier like a mid-length leather skirt or trousers with heeled boots.” — Sara Watson 

“The element I often avoid are miniskirts. I don’t like to show my legs a ton, hence I tend to go for a leather midi skirt mixed with silky tops. Overall, I tend to go for pieces that are fun, unique, and stand out in a crowd—like a unique blazer, puff-sleeve tops, or one-shoulder tops combined with oversize jeans and colorful heels.” — Jazdzyk

“There is very little that I restrict myself to not wearing, but my rule of thumb has always been that if I have to fidget with it, then I’m not going to wear it. So I stay away from super-short items when it’s time go out. I want to be comfortable without thinking about how I look all the time. When I go out, I gravitate toward  mid-length dresses, jeans, and a fabulous party top.” — Hosey

Next, check out what a woman over 60 is buying for the holidays.

Sienna Miller Wore the “Boring” Flats Trend That’s Back From the Dead

Most of the Sienna Miller paparazzi photos these days are of the busy actress and mom out and about on the streets of New York. That’s why she’s a trusted source for flat-shoe trends, as she’s often spotted wearing them. (If you’ve ever been to NYC, you get it.) And while out earlier this week, Miller wore a casual fall outfit that was tailor-made for weekend errands and the like, yet stylish to a T.

In this instance, Miller wore a puff-sleeve sweater with straight-leg jeans and a Gucci bag worn crossbody. On her feet, she wore a “boring” flat-shoe trend that you might have thought was over in recent seasons but that the fashion industry has been buzzing about and brands have been embracing as of late: ballet flats. Miller opted for the most fashion-forward iteration of the trend, which includes an elongated toe and soft leather material. The low-key flats are certainly on the classic end of the trend spectrum, so you can rest easy in knowing that they’re probably not going to be passé again anytime soon.

Scroll to shop Sienna Miller’s easy look and some of the ballet flats that we highly recommend.

On Sienna Miller: Apiece Apart Merel Funnel Neck Sweater ($375); Gucci GG Marmont Quilted Leather Bag ($2290) 

Next, 11 on-trend ways to wear jeans with flats.

Anna Wintour Reveals the 4 Best Coat Trends Right Now

Anna Wintour is getting into the holiday spirit. In the newest video for Vogue‘s Go Ask Anna series, she was asked several questions about gifting, holiday parties, winter trends, and more—and of course, she knew exactly how to answer each. When someone asked her which celebrity she should look to for holiday outfits, Wintour answered Kate Middleton without hesitation. “She always looks absolutely impeccable.” And as for the gift you should give your mother-in-law, Wintour has a genius idea: a framed photo of your partner with your mother-in-law. 

On the winter-style front, Wintour was asked for her tips on shopping for a new coat. “Yes, absolutely,” Wintour says in the video. “You should look at Vogue‘s November issue where we have a wonderful shoot styled by Tabitha Simmons and photographed by Dan Jackson, and the coats are worn by Kendall Jenner. There’s everything from a great little Burberry check puffer to a Versace fake [fur] leopard coat, Max Mara red military look, and a wonderful Marc Jacobs [oversized] topper. I really think there’s a coat in there for everybody.” Scroll down to shop the four coat trends she mentions. 

Next, Anna Wintour says these are the eight biggest trends of 2020