Our Favorite Summer Outfits—Women Over 55

What are you wearing when you go out this summer? I know what I’ve been living in, but I want to give you a variety of looks. So I asked some of my stylish girlfriends, all aged 55+, what they are rocking this summer. And as you’ll see, they came through.

My Favorite Summer Outfit

White jeans are always classic, but my favorite outfit to wear out in Chicago is a mid-length skirt with a knit top or tee, walkable shoes and a crossbody bag. I try to mix up the pattern and texture of the top and bottom. This basic formula works with flats, sneakers, booties or heels and can easily be layered. For me, this look is more flattering and versatile than a dress. The longer length of the skirt is comfortable to walk and sit in (no bare thighs touching the seat). And if I eat too many tacos on the Riverwalk, I’ve got room to expand.

Here are a few recent pics of me wearing this combo. The black Last Tango skirt, $89, is my absolute go-to for travel. It doesn’t wrinkle or show stains, goes with everything, is nice and stretchy, and has deep pockets! I took it to Ireland in May and was so happy with it.

My Friends’ Favorite Summer Outfits

This summer is a hot one, so it’s no surprise that many of my girlfriends are leaning toward dresses and skirts instead of pants for social events.

My fashionista friend and frequent collaborator Berit is embracing easy, breezy eyelet this season. “It’s my quintessential summer favorite fabric” she says. She’s found some very affordable pieces that, as you can see from her charming Instagram post, are feminine, fresh and classic. Her wardrobe and sense of style are truly amazing, so follow her account @berits.bits if you’d like to see more.

My lovely Florida gal pal and tennis partner, Linda, has figured out how to beat the heat by wearing flattering, flowing dresses from J. McLaughlin like this one (she has several). “I just don’t want to wear anything tight or clingy,” she says. It’s an instantly pulled-together look and you can see from her smile how relaxed and happy she feels!

My college bestie/sorority sister, Tricia, also has a dress she’s loving this summer. This IBKUL Solid Sleeveless Mock Dress, $120, is cool, chic and has handy zip pockets. The fabric is breathable and sun protective, so it’s perfect for an active person like Tricia. She’s pictured wearing it out to dinner in the trendiest color of the season, Barbie pink, with matching Birkenstock sandals and a white jean jacket. Tricia spends a lot of time traveling for her consulting biz, and loves wearing this dress on the plane, because it’s comfortable and doesn’t wrinkle.

My stylish Lincoln Park tennis friend Maureen knows how to dress for her shape. She’s long waisted, so she opts for shorter sundresses and skirts that emphasize her slim waist while giving her a leggy look. She’d feel frumpy in longer skirts like mine. It’s so important for women our age to know what feels and looks best on our bodies, rather than following trends that don’t suit! I snuck the second pic of Maureen at our tennis picnic this weekend, because not only is her white outfit a perfect example of her figure flattering silhouette, she’s wearing Berit’s favorite fabric, eyelet!

I love seeing what my friends are wearing this summer, it’s fun and inspiring. Hopefully this post has provided a little summer style inspiration for you too. But the main thing is to wear what makes YOU feel good—and stay cool!

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