Summer Dress Lookbook for Women Over 50

Welcome to my 2024 Summer Dress Lookbook. I’ve rounded up the dresses I’m enjoying wearing this summer to share a little style inspiration. I’m also sharing great accessories to complete these one-and-done summer outfits. So whether you’re here just for the inspiration or to shop, I’ve got you covered with this Summer Dress Lookbook.

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Not every dress will suit every woman. But I have a feeling you will indeed find a few dresses that really resonate with you. Some will even mimic those in your own closet, so maybe you’ll see a new way to accessorize them. Remember, dress length is also a personal choice. Sometimes we choose our dress length to present the most body-flattering effect. Other times we choose a dress length to express our personal style, to fit an occasion or to show some personality. Let’s have fun with this!

The Chambray Relaxed Ruffle Midi Dress from Me+Em

The Chambray Relaxed Ruffle Midi Dress from Me+Em is actually part of their current sale, so it’s half price. Unfortunately its only available in a couple of sizes. But I do suggest you check out other dresses offered in the Me+Em sale because they have some gorgeous offerings.

Me+Em is a London-based brand with stores now in New York as well. Since I saw literally dozens and dozens of women in London wearing sneakers with their dresses of all styles last summer, I thought it was only fitting to wear this Chambray Relaxed Ruffle Midi Dress with my Retro Trainers, also from Me+Em.

Style Tip: Don’t hesitate to wear your dresses with sneakers. It’s so on trend and comfortable to boot! I generally suggest classic white leather sneakers, like the Paul Green Unity platform sneakers or these more economical Cole Haans or Keds, all in the Nordstrom Anniversary Sale. But field sneakers like my Retro Trainers or these Adidas Sambas can work nicely, too, for a different vibe.

Talbots Side Tie Midi Dress

The Side Tie Midi Dress below is marked down and you can get an extra 40% off right now. I didn’t really style it below since I was just trying it on. But I’d complete it with metallic or nude sandals. Then again, those sneakers would work, too.

A dress like this Side Tie Midi Dress works nicely for a backyard gathering during the summer.

Talbots Effortless Jersey Polo Dress

The effortless jersey polo dress below became a fast favorite. It’s cool and oh so easy to just slip on and go.

This could even make a great travel dress because the fabric is cool to the skin and wrinkle resistant.

The Spartina 449 Lea Midi Dress

The Spartina 449 Lea midi dress is the quintessential vacation dress. This is a great option to slip into for that evening out after being on the beach all day.

The Lea midi dress is not currently on sale, but it has been. So I suggest you “favorite it” in this LTK post so you’ll receive a notification when it is marked down. Just make sure you’re signed into your account, then click on the heart on the photo of this dress. I’m tell you, that LTK Shopping app is worth having and using!

J.McLaughlin Annora Linen Dress in Jardin Mariposa

This Annora linen dress in the bright and beautiful Jardin Mariposa print is another of my favorites. Not only is this dress bold and cheerful, but it’s extremely comfortable to wear.

Complete the dress with nude sandals and a straw bag for the quintessential summer look. The Annora linen dress is 41% off and available in sizes XS to XL.

Style Tip: If you’re trying to create the most figure flattering effect, you’ll do well to complete your dress outfit with flesh-toned sandals. Those will elongate your legs and look oh so chic. But you can get a similar effect with any sandals that have a low profile and low intensity.

The Elena shirtdress from J.Crew

The Elena shirtdress from J.Crew is currently marked down a little and still available in most sizes. It comes in chic black, too. But white dresses are so on trend for summer 2024.

Style Tip: To avoid looking washed out in a white dress, be sure to wear a pretty lipstick and add a little color to your face.

The Colette Wrap Midi Dress

Oh my goodness. Here’s another favorite. This Colette wrap midi dress is just so flattering. It’s marked down, but almost sold out. But I love a dress with a removable sash that can be replaced with a belt, as I usually do with this dress.

This dress is from Anthropologie, where you can always find beautiful, unique dresses. They cater mostly to a younger clientele, but they do have selections, like the Colette wrap midi dress and others, that are perfectly suitable for us more mature women.

The Veronica Beard Arwen Stretch Linen Skirt

Because I only have one skirt to share anyhow, I decided to include it in our 2024 Summer Dresses Lookbook. The Veronica Beard Arwen stretch linen skirt definitely deserves a shout out. It’s not a one-and-done, of course. But it doesn’t take much to complete this beautiful, timeless skirt.

I like to top mine with either a colorful silk blouse or a linen shirt, like I did above. The Arwen skirt is currently marked down and still available in most sizes. Yes, it’s pricey, but the quality is so impressive and it’s a timeless staple you’ll reach for over and over.

The Veronica Beard Seymour Silk Dress in Wildberry

I wore the Veronica Beard Seymour silk dress for a special evening on my Alaska cruise. The photo below is not the best and I look a little worst for the wear after a long day of excursions. But this silk dress is a knockout. It’s also available in black, but I love the wildberry.

I’ll definitely wear this timeless, elegant silk dress again. And it’s still available and marked down 50%. If you have a special event you’re planning for, definitely consider this frock. I know the plunging neckline may be low for some. But because I’m just not busty at all, it really was not revealing on me.

Style Tip: It’s so important to wear the right undergarments with dresses. I always wear either cooling shorts like these from Thigh Society (with casual dresses and skirts) or shapewear with dresses. And make sure you have the right bra, too. With the Veronica Beard silk dress above I wore this adhesive “bra.”

Jude Connally Dresses

Just recently I was invited to become a partner with Jude Connally. I had ordered several of their dresses and shown them on Instagram and in this blog post. I’m so glad they reached out to me because now I can offer you a discount at their website. You can use code KAY15 for 15% off your purchase at Jude Connally. But yesterday the FFKAY code was still yielding 25% off. Worth a try!

I love wearing these pretty Jude Connally dresses in Jude cloth. It’s soft, silky and moisture-wicking. So it keeps you so cool and comfortable on hot, sticky days.

You know I’m usually one to wear more subdued tones, but I have thoroughly enjoyed the bright colors of the Jude Connally dresses, too. They’re cheerful and distinctive.

I have the Susanna Dress in Jude clorth in both Trellis Trio Aqua (above) and Moroccan Trellis Berry (below). I could have sworn that I ordered both dresses in the longer version, but the aqua dress looks shorter than the berry one, so I must have only gotten the longer version in the latter. At least that way you can see the difference. Keep in mind that I am 5’8″.

I find all of the Jude Connally dresses to be super flattering. But they’re also very comfortable and versatile.

J.Jill Cotton-Gauze One-Pocket Shirtdress

Cotton gauze is so on trend this year. We’re seeing it everywhere. And I can attest that this cotton-gauze one-pocket shirtdress from J.Jill is super comfortable and surprisingly flattering. You could certainly belt this dress for a more defined waistline. But because the cotton gauze is rather thick it felt to me like it looked a little “bunchy.”

And really this is one of those dresses that is meant to be very relaxed. My wild orchid Cotton-Gauze One-Pocket Shirtdress is now 40% off but almost sold out, as is the persimmon. But the beautiful royal blue is fully stocked in sizes XS to 4X.

Eileen Fisher Washed Organic Linen Délavé Shirtdress

Another favorite dress that I wear over and over this summer is the Eileen Fisher washed organic linen délavé shirtdress. Good news! This gentle, timeless linen dress is now over 50% off.

I always size down in Eileen Fisher. I’m wearing a size Small very comfortably.

Frank & Eileen Lauren Polo Dress

As I’m writing this post I’m actually wearing our final dress in my 2024 Summer Dress Lookbook. It’s the Frank & Eileen Lauren polo dress. This cool, comfortable dress is perfect for an everyday kind of summer day.

I size up to a large in this dress for a very comfortable fit. It’s available in other colors here, but the sizes are somewhat limited. My magenta dress seems to be well stocked only at Nordstrom.

Thanks so much for stopping in. I’ve really enjoyed wearing dresses more than I thought I would this summer. What about you?

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