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The 3 Most Flattering Dresses For Mature Women

Figure Flattering Dresses For Mature Women - collage: sheath dress; fit and flare dress; shift

Finding Your Most Flattering Dress Style

’Tis the season for weddings and graduations, which means you might very well be seeking out flattering dresses for mature women! I love a good party, event, or gathering, but deciding what to wear can easily be the most stressful part.

Figure Flattering Dresses For Mature Women - navy dress with red clutch and scarf

There are a lot of factors worth considering when looking for a party dress, including color, price, length, and so on. But for women such as myself with “mature figures,” it helps to first consider the shape or style of the dress. Because a dress that flatters your figure will ensure you not only look great, but feel confident too!

Related: The 13 Fashion Essentials For Dressing Your Best Over 50

So for the benefit of my fellow older ladies out there, I thought we’d take a look at 3 of the most flattering dresses for mature women in this post. After reading this post, you’ll know exactly what to look for when you’re shopping for a dress for a special event! :-)

Figure Flattering Dresses For Mature Women - woman in a navy dress using a gauze scarf as a cover-up

The 3 Most Flattering Dresses For Mature Women

Picking out the most flattering dress style for yourself depends on your shape and personal style. And once you know the shape of dress that looks best on you, the rest is just picking out your favorite colors and accessories — you know, the fun stuff!

Read on to discover the most flattering dresses for us middle aged and older ladies with more “mature figures”.

Related: 7 Practical Fashion Tips That Will Liven Up Your Look

Figure Flattering Dresses For Mature Women - woman in a red sheath with a black shrug

1. The Sheath Dress

The sheath dress is a long, lean, body-hugging style that enhances your curves and defines your waist. It is sleek, classy, and works for nearly any occasion! Michelle Obama is well-known for frequently sporting sophisticated sheath dresses.

Figure Flattering Dresses For Mature Women - low heel green velvet pumps

You may be on your feet for hours, so a pump with a low heel looks great without the pain!

Figure Flattering Dresses For Mature Women - woman in a red sheath with a navy shrug

Choose a sheath dress if…

  • you have an hourglass figure. This dress will really show it off!
  • you have a straight or thick waist. A sheath dress can help define and enhance your waist.

Sheath dresses can be tricky if…

  • you have unique body proportions.
  • you have a large tummy.

Related: 9 Grooming & Style Mistakes That Make You Look Older

Figure Flattering Dresses For Mature Women - woman in a white shift with a black crocheted shrug

2. The Shift Dress

It’s easy to get “shift” confused with “sheath” when it comes to dresses, but they couldn’t be more different from each other! Shift dresses hang loosely from the shoulders and fall straight down to the knee area. These dresses can have a variety of sleeve types and necklines, and they give off a casual, relaxed vibe.

A loose shift dress can be great for covering areas of concern around your waist or hips! Shift dresses can also be a great choice for summer events like weddings because they tend to be nice and cool, especially if you choose a light cotton or rayon.

Figure Flattering Dresses For Mature Women - small silver purse with chain; gold metallic sandals with low narrow heels

My favorite part of shift dresses is how comfortable they are! I could easily wear a shift dress all day and not feel the need to change into something comfier. (I can’t say the same for the shoes I wore in these photos, but on the other hand, I’ve never been able to say that about any pair of heels!) :-)

Figure Flattering Dresses For Mature Women - woman in a white shift with a small silver purse with shoulder chain and a black crocheted shrug

Choose a shift dress if…

  • you have a boyish, rectangular shape.
  • you’d like to de-emphasize your midsection, hips, or thighs.

Shift dresses can be tricky if…

  • they’re too baggy, since that might make you look shapeless.
  • they’re too short. Throw on a pair of tights or leggings under the shift dress for an easy fix!
Figure Flattering Dresses For Mature Women - woman wearing a navy fit and flare dress with a gauzy red scarf over her shoulders

3. The Fit-And-Flare Dress

The fit-and-flare style is one of the most consistently popular dress silhouettes, and for good reason! This dress has a fitted top, a defined waist, and a flared skirt. The fit-and-flare dress is a favorite for many women (including me!) because of its very flirty and feminine shape! It’s the most flattering dress style for a variety of figures!

Figure Flattering Dresses For Mature Women - woman holding a small red clutch open to show the leopard lining

This fit-and-flare dress ensemble is so fun to wear, and it’s as comfortable as it is cute!

Figure Flattering Dresses For Mature Women - woman in a gauzy red shawl and navy dress cutting a slice of pie

Choose a fit-and-flare dress if…

  • you want to balance out a large bust. The wide skirt can create more of an hourglass silhouette!
  • you want to draw attention away from your hips and thighs.

Fit-and-flare dresses can be tricky if…

  • you want a sophisticated look. Certain lengths and patterns can create a vibe that is more “little girl” than “grown woman.”

Related: This Easy Fashion Hack Will Make You Look Slimmer In Seconds

Figure Flattering Dresses For Mature Women - woman in a red sheath pouring a glass of champagne

What styles of dresses do you usually gravitate toward?

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  • Great styles. I usually have a matching sweater. When I wear dresses it’s weekly for Church services. They also tend to crank the AC up and it also great for colder months inside our building.

  • To all you readers who ‘know better’:

    You are adults (maybe?). When advice is out there, take what you feel applies to you. Then keep on going. Others will do the same. You are NOT the fashion police.

    Jillie, you ROCK!!!

  • Jillie, you are a lovely fashion model. I appreciate your taking the time to share some figure flattering ideas. I love the way you educate me on such a variety of things… As for the comments from others, call it a shrug or call it a short cover up, it’s still in fashion. I was recently fitted for an evening gown that has a short cover up by s very reputable local seamstress and I love it. As for the shawl, I have many that have wrinkles as part of the style. As for shoes, it’s a matter of what looks best on you. So what I’m saying is this……. jillie showed me 3 possible styles with shoes and I enjoyed reading about them without having to leaf thru a bulky magazine. What a treat. Happy Thanksgiving to all.

  • and you may be able to rock it as you say. Wonderful for you!……not everyone can and look silly. I will never wear used clothing we all have foibles. You can read my comment above if you are interested.

  • I ‘m 71 and can understand where Satindoll’s strong standards are coming from. However, isn’t party dressing about fun and feeling pretty? A woman who chooses attire which make her feel her best, exudes confidence!
    Jillie’s taste may not be everybody’s cup of tea, but her heart is always in the right place!

    • I applaud all you ladies who jumped on the defend Jillie bus. Perhaps I should have taken paragraphs to explain instead of a quick comment. My intention was not to insult or hurt anyone’s feelings. Some people can get away with some things that others cannot. I come from the school of if a friend wants the best for me and not have people laugh behind my back then I will listen. I was attempting to be helpful. When you do the same thing for 40 years it’s time to change; we cannot hang on to youth forever. I feel that when you are in the public eye especially (photos) and giving your opinion or passing along helpful hints than you should look the part. I imagine people want to be taken seriously. I.E., I would not take seriously a 350 lb Doctor who smokes telling me to lose weight and quit smoking. Get where I am coming from? Hey, if ya’ll feel great and confident wearing 5 inch heels when you are 80 go for it! But, don’t you think that would look ridiculous???

  • I think Jillie is great but she missed the boat on this one. Shoes with ankle straps make your legs look heavier. A tan/beige pump would have been much better. It would have have elongated her legs and have been more age appropriate. Also shrugs are for middle or high school students. A beautiful well made jacket would have been classy! Sorry Jillie, love your posts but not this one. PS the red shawl needed a good ironing.

  • One other comment in regard to used shoes. Never for me. I have no qualms about shopping at used clothing stores -especially for wash and wear stuff. If friends want to swap clothes, great. Much of my wood furniture has come from used stores and lovingly restored. I haunt the Goodwill stores. But shoes? NOPE.
    I used to work for a podiatrist. You would be horrified to see the amount of nasty diseases people carry in their feet and toenails with fungus being the most common. It is easily transferable via shoes and hands to others, common in those with certain diseases. I have a foot size that is commonly on display at stores. I used to just try on the “display” shoes as I looked. No longer! I try to find shoes that haven’t been tried on. And as soon as I’m home, I scrub my feet. Anyway…just a word of caution to those interested.
    PS: I no longer go to pedicure places for the same reasons.

    • Occasions that require me to dress up are few and far between. I cannot fathom buying new shoes that I’m only going to wear once or twice. It makes financial sense to head to my local GW or SA to find a nice pair of fancy shoe. A few spritzes of antibacterial shoe spray are good enough for me. I think all the options above look adorable on your Jillee! Please keep them coming.

  • Hello Jillee,

    All three dresses look lovely on you. May I make a suggestion, lose the shrugs and scarf (said with the best intentions only).

    You are a very attractive woman with a nice figure. In my opinion, you would look much nicer wearing only the dresses.

  • I’ve been a little hesitate to do much order of clothes on line, due to the variance in sizes among the different brands. Is it easy to return things that don’t fit? Do you have to pay return postage?

  • Jillie, you are the cutest thing going. Love you in red or red accents. I just started wearing fit and flare styles when I am not wearing tunics and leggins. My hair is long also and I think it takes a certain type of personality to wear that as we get older. I am tall and can wear just about anything but midi length. As my daughter says to me and I in turn to you “Go for it”

  • In my opinion, find a knit black dress that fits your body and personal style. Then add color with your accessories. I find that my three black swing dresses, one long sleeve a second short sleeve and the third sleeveless, not only feel great but receive compliments every time I wear them. All three purchased on line with 40% off and free shipping from Old Navy and less than $14.00 each. It took me one season to find all three but has been well worth it. I even picked up extra dresses for the future and packed them away! I know a good look when I see it. For the record, 65 years old, 5’4″ and 137lbs. Used clothing is a great option that saves money and often makes it possible to buy fantastic clothes which when new are beyond your budget. Almost all of my shoes are used and were purchased on line. And I have a tricky size to find. Find a good shoe repair to bring the heels and soles up to snuff if needed. Buying second hand pays off big. And it is fun to know how much you saved and how great you look!

    • I agree with your concept, however, if I wear a black dress I look like I am going to a funeral. Black drains my colour, not everyone looks fab in black (pants and skirts are fine). I choose navy. Think of the different accessories you could pair. I just thought I would throw in a suggestion.

  • I second the praise for ThredUp! I’m on a tight budget, and needed a few hot-weather dresses for my son’s wedding in Costa Rica. With coupons and first-time discounts, I bought beautiful several silk (!) shifts and a couple of other pieces for about $100. They have literally thousands of items–you WILL find something! A great company. And readers, please set your politics aside for five minutes–this post is about affordable, stylish CLOTHING, for heaven’s sake. Haters are welcome to look dowdy AND pay full price, if it makes them happier. Thanks for a great post, Jillee!

  • I’m terribly short and slightly overweight. I have a difficult time trying to find things that look good on me. I don’t buy clothes on line as I have to try on everything and would end up spending money to return most of them if not all. I actually prefer a skirt and blouse or a nice pair of dress pants with sparkly top and a pair of low heels. Most dresses the last 10-15 years are WAY too long for me and can’t be hemmed because trying to cut off 6 to 8 inches ruins it’s shape.

    • Check the petite sizes section in stores. That’s what I have to do. A lot of the styles don’t require hemming and some just slightly. Believe me, I know how frustrating it can be.

    • I agree. I usually wear lovely “evening pants” and sparkly or fancy overblouses and low heels because I am past the age of wanting to be trendy and in pain! This works well when traveling or cruising. No dresses for me. Everything, even petite length has to be hemmed to the right length for me.

  • I love all three dresses on you and the cover-ups. You look super nice, elegant with a touch of playfulness, which I think is perfect for the holidays. In my opinion you can mix and match all six pieces, I think the red scarf would look beautiful with the white. I love the blog, such good ideas on so many subjects. See you tomorrow.

  • The Fit and Flare Dress, would be the best for my wife,as she is very short, and has little bite of a wast, I think they call them c hailed Bering hips. She is only 4’10” and I am 6’8″. You look very good in all of them,pays to have a bite of height. Are you going away for Xmuss, Hope you have a good one for you all All owner love from Down under Lofty & Cheryl Have a safe time Jillee.

  • Great styles. I have a hard time wearing shorter dresses. I’m Petite and my weight tends to fluctuate. I’m by no means an old bat. I try to wear longer dresses that don’t require me to wear full length nylons. I tend to get an ugly rash on my legs due to food sensitivities and some of them make me feel bloated. I have over the years bought holiday type sweaters when they go on clearance after the holidays. I can pare them with longer skirts which are more physically comfortable to wear and I don’t feel as self conscious about the rash.

  • I think that choosing a dress for shape takes precedence over age. Age basically needs to be long enough. Dresses for one’s shape calls for a bit of knowledge of we don’t have perfect figures.

  • Love your blogs Jillee. I don’t mean to sound critical but just want to ask that when you show us dress ideas you could maybe include a pic of you wearing the dress without a shrug, shawl etc please. The fit and flare spotty dress looks lovely for example but I’d like to see how it looks on you, not covered up with a big shawl which (in my experience) always gets discarded during the evening. In my mind, most of these pics look like someone not very comfortable in how they look in the dress they’re wearing.

    • I fully agree with Beth. But also, and personally I think even more important than Beth’s point of covering up, is simply that shrugs don’t look good on anyone. Well, perhaps the cute little 8-10 year old, but otherwise…. Some of you may like them, but I find them to be terribly unflattering and while I don’t follow fashion trends closely, it seems I rarely see shrugs being worn. (That may be the reason they are being sold on Thred Up – people getting rid of them).

      • Hi Susan, I disagree about ranking the importance of the points made by Jillee’s followers. I don’t have an issue about people choosing to cover up and have no point of view as to whether shrugs etc are flattering. My point is simply that the item is about dresses suitable for older women so I’d like to see the whole dress, e.g. the sleeves aren’t shown on any of them.

      • It looks to me that all these dresses are sleeveless. Upper arms are often an area many women don’t like about their figures, hence the use of shrugs and other cover-ups. I know MY chubby upper arms are not for public viewing.

      • Me three Karen I’m no lightweight and my upper arms and elbow dimples are just not for public display!

      • Beth, I have no idea what you are referring to in terms of “I disagree about ranking the importance of the points made by Jillee’s followers”. I was merely agreeing with you in terms of your statement ” want to ask that when you show us dress ideas you could maybe include a pic of you wearing the dress without a shrug, shawl etc please”. If you read carefully,you will see a “but…” after I agreed with you. Meaning…I agree with that, but…and gave my opinion on shrugs. In short terms, I hate them, think they are ugly and unflattering, but if others like them, fine.
        Anyway, have a nice day and everyone – please try not to be so quick to attack. Treat people nice at the grocery story, shopping mall. Our world is filled with so much ugly. Can’t we disagree and still be nice?

      • Oh dear Susan, an online squabble? I did read your comment, carefully “..even more important than Beth’s point of covering up” (which I was trying to explain wasn’t my point). You appear to say you feel your point of view re shrugs, cover ups etc is more important than my request, simply that Jillee might please show us her in the dresses with no cover up, as the article is about the dresses i.e. not a debate about the fashion status of the accessories or whether one should/shouldn’t cover up. I’ve no intention to offend or contradict anyone and apologise if I have, just wanted to clarify my simple point and request.

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