little black dress

Top 9 Dresses for Women Over 50 That are Classic and Chic

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Dresses are a must-have for every wardrobe. Not only are they feminine, but they’re more versatile than you think-not just reserved for fancy occasions. But for most people, what comes to mind when they think of dresses for women over 50, are usually outdated prints, unflattering silhouettes, and shapeless floor-length denim. And well, they’re not always wrong.

If you’re hesitant to wear dresses because you think they’re too fussy or you don’t know which ones you should have, this post has dress styling tips as well as the top 9 dresses for women over 50! No one will confuse you for old-fashioned or dowdy in these picks. These dresses will have you looking like a sophisticated and classic woman over 50 in no time!

A few things to keep in mind before you shop

Body Type

You want to highlight your best features, after all! Think about your body and what you want to highlight or minimize. If you aren’t super confident about your upper arms, then look for long sleeve dresses when it applies. Once you feel happy in what you’re wearing you can just feel your confidence levels increase. Some universally flattering dresses for every body shape are a wrap dress and a fit and flare dress- but oops, I just gave of the dress styles away. We’ll get to them soon!

Generally, the best lengths for women over 50 are knee-length, then midi, then maxi. To dress chic and classic as an older woman, try to steer clear of mini dresses.

Take into account your personal style as well. If you really can’t see yourself wearing something, then don’t get it! You don’t need it to take up space in your wardrobe and add clutter to your home.


Generally, solid colors are best for these classic pieces so you can wear these again and again, in different ways to different occasions. Not only do solid colors (or very subtle prints like houndstooth or tweed) add versatility to your pieces, but they keep the classic aspect as well.

On the topic of colors, when shopping for a new dress, look for the colors that flatter your skin tone the best. If you shine in black, get more black options! If you are a redhead and glow in camel, then look for a dress in a camel hue instead.

Though you want the majority of these dresses for women over 50 to be in neutral colors, there are a few different styles that you can have some fun with.

Top Dresses for Women Over 50 That are Classic and Chic

This list of dresses for women over 50 includes the top dress styles for your wardrobe. Whether it’s for a special occasion, work meeting, or casual event, these are the best dresses that are the most flattering for your age and provide the most versatility.

1. Sweater Dress

A sweater dress is one of the best options to have for fall and winter. A midi-length sweater dress will look great with knee-high boots or other equally stylish boots. A sweater dress can also work for casual outfits too. Just pair some white sneakers and a moto jacket with it and you’re good to go!

This style is great for a woman over 50 because even though it’s a classic, it’s “in” at the same time, updating your wardrobe. Plus, not only is it cozy to wear for the cooler seasons, but it’s comfy too!

This dress is best chosen with long sleeves. If you prefer a more fitted style, opt for a figure-hugging sweater dress. But generally, something that grazes instead of clings is better for older and mature women.

If you feel like switching up your look, experiment with adding different scarves, jackets, and tights.

2. Shift or Sheath Dress

These two are easily confused, but for good reason. They are pretty similar, so you probably don’t need both styles in your wardrobe. Nipped in at the waist and structured towards the knee, a sheath dress is more fitted. Whereas a shift dress falls straight from the shoulders, with just a few nips at the bust.

A sheath dress is sometimes best worn for work or professional occasions, as it looks more professional and polished. With a dress like this, make sure you have the perfect fit. Banana Republic has a lot of great work dresses like this.

A sheath dress is great for an hourglass body type and the long lines can elongate your figure and hug your curves. Sleeveless styles are great for layering a blazer over too.

A shift dress is a bit more casual, as the silhouette isn’t as structured. This one can more easily be dressed up or down. If you find that you need a good work dress, choose the sheath dress. If you want a classic dress that can be dressed up and down, choose the shift dress.

3. Little Black Dress

A fashion staple, you can’t talk about classic style without mentioning the LBD. Some of the perfect shoes for this style of dress when you want to be dressy are high heels, block heels, and kitten heels, and thankfully, there are many different heel heights out there if when you think of high heels you immediately think of sky-high stilettos. And pain!

However, pointed-toe flats can give off a dressy look as well and ballet flats can look chic.

Related: How To Master Fall Fashion for Women Over 50

4. Sundress

You may think that younger women have the claim on a sundress, but it’s not true! An easy and fun sundress belongs in an older woman’s wardrobe as much as it does a younger woman.

Some of the best sundresses are versatile enough to wear all spring and summer, but fun enough to make a statement too! For your best sundress, look for easy and flowy, such as a linen smock dress, white eyelet dress, or something with a floral print.

A great way to wear your sundress in the warmer months is with strappy leather sandals and a straw bag. In the spring season when you can’t wear sandals yet, pair your sundress with mule slides, white sneakers, flats, or closed-toe espadrilles.

5. Wrap Dress

Wrap dresses are iconic for a reason. Whether you’re 25 or 55, this style of dress is universally flattering and is perfect for crafting a classic look.

Spring, summer, fall, or winter, this is a great option that you can wear the majority of the months as well-with just a few different styling tips! A wrap dress can look especially great on a pear body shape too.

Related: How To Wear a Wrap Dress Like a French Girl (in All Seasons!)

6. Party Dress

Party dresses and cocktail dresses don’t get worn all the time, but it’s still worth having one in your closet that you can break out last minute for any cocktail parties or special events.

Since you already have a little black dress, why not have some fun in this area and try out something with brighter colors? Or this formal dress could be made of lace or have sequins on it. A slinky slip dress totally works as party attire too.

It could have long sleeves or be sleeveless. If you already have a sleeveless dress but you don’t want to show much skin, you can easily add a sheer cardigan or a sequin jacket for some added party style.

7. Animal Print Dress

Everybody needs a little bit of “vavoom” in their wardrobe! An animal print dress is great to wear when you’re feeling bored or just want to jazz up your everyday look. Animal print, like a leopard print dress, looks great in the fall and winter as much as it does in the summer.

Maybe leopard print isn’t your thing, but what could you get that would fit into your signature style and be fun to wear at the same time?

8. Fit And Flare Dress

Sometimes called skater dresses, a fit and flare dress is a great dress style for many body types! This style creates definition around the waist (fit) and flows out (flare) minimizing your bottom half instead of clinging to it. Not only does it help to create curves, but it can help define what’s already there.

Just like the wrap dress, this is a universal and versatile style that will be a great addition to every woman’s wardrobe.

9. Shirtdress

Carolina Herrera, fashion designer and style icon, was frequently seen wearing a button-down shirt with a skirt. This iconic look became her signature style, thus resulting in her collection of many chic shirt dresses.

A utility shirt dress, or just a plain shirt dress, is a classically chic style and a great way to look more put-together.

Fashion tips to get the most out of your dresses

  • Layer

The best way to switch up the look of your dress is to style it with layers! You can knot a button-down over a sundress or add a cardigan to a sweater dress. Think of all the layers you have in your wardrobe (trench coat, cardigan, blazer, moto jacket, denim jacket) and then mix and match with these 9 different dresses!

  • Accessorize

Want to jazz up a dress and make it feel new again? Accessorize! From brooches to necklaces, watches to scarves, there are so many pretty little things you could add to your dress to make it feel fun and different.

  • Switch out your footwear

Another way to get the most out of your dresses is to switch out your shoes. If you always wear heels with your shirt dress, try wedges. If you always wear flats with your shift dress, try sneakers. You can make a dress work for a completely different occasion just by switching out your shoes.

The types of dress styles out there are endless. From empire waist to peplum to tiered, we’d be here all day (and more) if I tried to list them out. But more importantly, even though those can all be great dresses, they don’t necessarily fit the top 9 (though your list might look different). But if you’re looking for a list to get you started on adding classic and chic dresses to your wardrobe, then start here!

From pencil skirts to camel coats, keep reading for the best clothes for women over 50!

Up Next: The Best Clothes for Women Over 50 Years Old To Wear

dresses for women over 50


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.