The Most Flattering Dress Styles for Women Over 40 (that Always Look Chic!)
Have you ever heard the quote, “Your dress should be tight enough to show you’re a woman but loose enough to show you’re a lady?” That wise advice came from legendary Hollywood costume designer Edith Head, and she was right!
Before you fall head over heels for the color, vibe, or even the price of a dress, take a moment to really look at the cut. I’ve found that if the shape doesn’t suit your body, it won’t matter how pretty it is, the dress just won’t look good on you.
The real secret? Finding a dress that fits and flatters your body type. That’s when the magic happens. Here are 7 classic dress styles I always recommend for women over 40—because they never go out of style and always help you look (and feel) Age-amazing.
The Most Flattering Dress Styles for Women Over 40
1. The Sheath Dress
There’s something so effortlessly elegant about a sheath dress. I adore this style. This sleek, body-skimming silhouette is a go-to when you want to feel put-together and polished. It hugs your shape (without clinging) and has clean lines, a structured fit, and often times a little slit or pleat in the back for to make it easier to walk around in.
It’s perfect for work, events, or any time you want to keep things classic and classy. Shapewear smooths out any lumps or bumps and makes you look svelte in this style.
- Best for: Hourglass figures (to highlight your curves), straighter or thick-waisted shapes (to help create curves).
- Watch out if: You have a tummy or your proportions are uneven—it can be less forgiving since it sits close to the body.
Find out why I always come back to the sheath dress.
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2. The Shift Dress
Shift dresses are the definition of easy style. They hang straight down from the shoulders, with no waist definition—almost like an elongated tunic. If you want comfort and coverage without clinging, this is your girl.
It’s great for casual days, travel, or anytime you want to look pulled together without trying too hard, and boy, are shift dresses comfy! No having to wear Spanx here!
- Best for: Rectangles, thicker waists, women with fuller hips or thighs
- Watch out if: You’re very curvy—it can hide your shape. Also, when it is too short or oversized, it can feel frumpy.
Tip: Add tights or leggings to give it a bit more shape and coverage because shift dresses are usually on the short side.
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3. The Fit & Flare Dress
This is the ultimate flattering style for so many women. With a fitted bodice and a flared skirt, it creates (or enhances) an hourglass shape and works beautifully to balance proportions.
It’s feminine, fun, and one of those silhouettes that almost always works—especially when you want to look a little extra feminine and pretty.
- Best for: Pear shapes (it floats over hips), fuller busts (the skirt balances things out), rectangles (adds curves)
- Watch out if: You’re going for a more sophisticated look—some versions can feel a bit too sweet or girly, or like something out of the 50’s.
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4. The Wrap Dress
The wrap dress is iconic for a reason. It flatters almost every figure and works for almost every occasion. The v-neckline elongates the neck, the tie waist defines your shape, and the soft draping does wonders for curves.
It’s been a style staple since Diane von Furstenberg introduced it in the ‘70s—and I’m convinced it’s one of the most versatile dresses a woman can own. It’s my favorite type of dress and when I’m not sure what to wear I know this will always be appropriate and classy. For more dresses for every occasion, see here.
- Best for: Hourglass, pear, apple, or straight figures—it enhances curves or adds curves where there are few.
- Watch out if: You’re very busty (a cami might help) or petite (choose a shorter hemline).
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5. The Shirtdress
Borrowed from the boys, but made for us—the shirtdress takes the structure of a men’s shirt and gives it a feminine twist. You’ll usually find buttons, a collar, sleeves, and a belt to cinch the waist. Whether it’s made of cotton, chambray, or jersey, it’s polished but relaxed.
Think of it as your wardrobe’s best casual multitasker: perfect for everything from errands to brunch.
- Best for: Rectangle and apple shapes since it has more of straight up and down shape. Hourglasses figures can wear it too, if there’s a belt. You don’t want to hide that hourglass waist ladies!
- Watch out if: It’s too boxy or too short (which is often a problem for gals our age) Balance is key here, and thankfully recently there have been a lot of midi shirtdresses.
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6. The A-Line Dress
Elegant and timeless, the A-line dress flares gently from the waist, creating a clean, classic silhouette that is very modern and suits just about everyone. It’s easy to move in, easy to style, and gives you a graceful, modern look without trying too hard.
- Best for: Almost every body type—pear, apple, hourglass, rectangle
- Watch out if: The fabric is too stiff or the cut is too shapeless—it can look more “bell or tent-like” than chic.
Tip: Choose flowy fabrics and aim for a hem that hits at the knee or mid-calf. Anything too short can look too cutesy, baby doll.
shop a-line dresses
7. The Empire Waist Dress
This one’s a dream if you’re looking to smooth things out and draw attention upward. The empire waist sits just under the bust, letting the fabric flow over the rest of your body in a soft, flattering line.
It’s a lifesaver for anyone who wants to fake a smaller waist and camouflage the tummy area, or just look a little taller.
- Best for: Petites, pear shapes, small busts, or thick waists.
- Watch out if: You carry weight in your midsection (shapewear helps). Avoid this style if your stomach is rotund. It can make you look like you are pregnant!
shop empire waist dresses
FAQs About Flattering Dresses for Women Over 40
What is the most flattering dress style for women over 40?
It depends on your body shape—but universally flattering styles include sheath dresses for their sleek lines, fit & flare for balancing proportions, and wrap dresses because they adjust to your body and define the waist beautifully.
How do I choose a dress for my body type after 50?
Start by identifying your shape—hourglass, pear, apple, or rectangle. Then choose dresses that enhance your best features. A-line and empire waist dresses are great for creating flow and comfort, while wrap and shirtdresses help define the waist and elongate the silhouette.
Can women over 60 wear wrap dresses?
Absolutely! Wrap dresses are timeless and work well at any age. They highlight the waist, flatter your curves, and can be adjusted for comfort, which makes them a favorite for women over 60. A faux wrap style is just as nice and a little easier to wear because you never have to worry about your wrap creeping open at the neckline.
Dress Style Wrap-Up
The right dress makes all the difference. It helps you feel confident, pulled together, and like the best version of yourself. Once you know which silhouettes work for you, shopping (and dressing!) becomes so much easier.
These classic styles have stood the test of time, and they’re not going anywhere. Whether you’re getting dressed for a wedding, work, a night out, or just a Tuesday, there’s something here that’ll make you feel Age-amazing.
You might also like:
- Spring Dresses for Women Over 40
- Comfortable and Stylish Travel Dresses
- How to Dress for Your Body Shape After 40
- Plus-Size Spring and Summer Dresses
Now I’d love to hear from you—what’s your go-to dress style? Is there one you’ve sworn off forever? Let’s chat in the comments
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I prefer wrap, a-line, fit and flare, and smite waist. Those suit me the best. Though I do have a couple sheath work dresses for when I need to look more professionally polished.
Hi Carolyn, the key is to know what works and stick with it. You can experiment a bit with news styles, but when you wear dresses that flatters your unique shape, you’ll always look like a million bucks! Sounds like you have that nailed! Cheers, Deb
The 5 I listed above are the silhouettes I wear.
I have a short and curvy figure, and empire, fit-and-flare, shifts, and A-line dresses tend to flatter me. I used to have an hourglass figure, but I’ve become more of a pear shape. This guide has been very helpful to me. I appreciate how it explains what styles flatter different body shapes and why and what styles might not be as flattering or “tricky.” Thank you for sharing this. The dress examples are lovely.
I usually like sundresses with the elastic bodice. They are flattering on a petite frame, and I had my Draper James one on yesterday. Thank you for the list! I saved some of the styles for reference.
Hi Bonnie, Thanks for dropping by! Cheers, Deb
Thank you for the very informative. I especially like that you mentioned who the dress style it is perfect for versus would be tricky to wear.
Amy, I’m so glad it helped. Body type is key when deciding the best dress for you. It can make all the difference in your overall look! Thanks for dropping by. Cheers, Deborah
Deborah, I would love to wear a wrap dress but they all are too low cut on me. I have even ordered the one from Amazon that you feature but it was the same problem. I think I need to look for a wrap dress in a petite size.
Very informative
Friendly looking Fashions….I’ll check back later!
I like what I see. I’m a young 63-year-old and quite shapely (well, I want to think so!)
Nice articles. Please include me on your mailing list.
I’m a fan of fit and flare, on one condition. The length must be just below the knee. Anything higher looks goofy and too high school on me.
Also a fan of short sweaters or jackets with swing dresses: very 1950s.
Great tips. The fit and flare is my favorite style because it is universally flattering
Hi! I love your blog. I Am 52 years old, 5 10, and 145 pounds. I am looking for a lovely summer dress to wear in Mexico for our family portrait and looking for blue color. I was wondering what kind of dress you would recommend. I don’t know if I should get a pattern or a solid dress for the family beach portrait. There will be five others in the photo Recommendations would be excellent T n M ro tine
Hi Martine, You’re friendly and tall and at the beach. What about a maxi dress? Generally, I recommend a solid color for photographs, but since you are at the beach, things are more informal, and there are other people in the shot, you could go for a fun pattern. You’re in Mexico, after all, so saturated colors like bright oranges, blues, greens, yellows, and reds would look great. You should coordinate your color/patterns with the others if you want the shot to look fabulous. Otherwise it may l, l, l, l, l, l ook like you “didn’t get the memo,” if you know what I mean. You don’t want to have clashing patterns or colors. Have a wonderful time!
Thank you for your advice, Deborah! I will look for a maxi dress… possibly with an interesting pattern. I don’t have nice legs, so I like this idea for that reason also.
There are some great options for cute maxi dresses that are inexpensive at Ross Dress for Less, TJ Maxx, Marshall’s, and Nordstrom Rack…some are casual enough to wear to the pool and are made of cotton t-shirt material, so they pack easily.
I love the look of wearing a dress. However, I quit wearing them when people stopped wearing hose. I am 57, and my legs are lily white and do not look good without a hose. Is it ever alright to wear a hose?
I always opt for hose if my shoes are closed-toe – and if not, I go with hose / Spanx down to mid-thigh; and use tan wipes on my legs and feet with a good pedicure.
I love the fit and flare but finding any dress that hits at the knee is impossible; they are all too short. Loved all of the dresses pictured.
I found a perfect style for me! A slightly A shape knit in a wild pink print with sewn-in “jewels” around the boat neck AND elbow sleeves. I loved it so much; I bought a similar one in turquoise!
I’ve recently discovered that I love the fit and flare silhouette! I was kind of off dresses for a long time, and I think it was because I was wearing styles that didn’t suit me. I find the fit and flare so flattering and comfortable! I see lots more in my future, especially with spring and summer!
Great article; I love sheath as well as wrap dresses.
Hi Antionette,
I’m also a wrap dress fan. It is also a very flattering style of dress on curvy gals to show off curves and non-curvy gals to create curves where there are none. Here’s a post all about wrap dresses.
https://www.fabulousafter40.com/how-to-wear-a-wrap-dress/
LOVE the fit and flare dresses – the shift dresses are shapeless so um, no. Sheath dresses – maybe. Of course I’ve never been a “dress gal,” but I’m 43 and decided to try something new this year and change my style a bit……which is why I joined this site! Making the transition into what is appropriate at 43 and what is NOT is difficult for me – thank you for a wonderful website!! :)
Hi Patti, so glad you joined our community. What you said is essential; you want to try something new. It’s good to shake things up a bit. We often get stuck in a rut buying the same old things that are not us anymore. It would help if you took a few chances to discover who you are and how you want to express yourself at 40+. When your clothes reflect the person you feel you are on the inside, it’s uplifting and exciting, and that shines through. Please send me a photo of you in your new dress, whatever you choose, and I’ll post it. Cheers, Deborah
I bought a navy sheath for my daughter’s college graduation in May. Versatile. However, I just never seem to get anything but a sheath style. I should try others, but lack of money holds me back. I love your blog, thank you!
Hi Jean, I think that’s the perfect dress for graduation. You can’t go wrong with a sheath for any occasion. It’s class all the way. Look for the best sales on dresses starting in June. That’s when all the summer things go on sale, and you will indeed find an excellent fit and flare if you want to try it for a reasonable price. This is an effortless dress style, so I think you will get a lot of use out of it too. Cheers, Deborah