Best Cocktail Dresses For Women Over 50: Styles That Wow

I don’t know about you, but I look forward to a good dress-up moment from time to time. It seems like the occasions don’t come around as often as they used to, now that I am aging gracefully. When they do come around, I know that I like to feel confident, polished, and age-appropriate. So when an invitation comes along that calls for cocktail dresses, I get a bit excited.

As we age, finding the right cocktail dress that we can feel wonderful in can get tricky. We want to look fresh and stylish, yet love the dress we are wearing so that we look forward to wearing it more than once. I am a believer that sometimes we need to create another occasion if we feel fantastic wearing something. So, I am going to round up some cocktail dresses that are flattering for women over 50 and share some great tips to help you find the perfect dress for your special occasions.

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Serious About Styling | SAS For Short wearing one of the Cocktail Dresses For Women Over 50 in red
Dress | Sandals Use code BETH15SPRING25 for 15% off

4 Cocktail Dresses For Women Over 50: Age-Appropriate Styles That Wow

In our 50s and beyond, we can wear cocktail dresses to a variety of special occasions. Social events like birthday and anniversary parties, fundraisers, weddings, and elegant dinner parties. One thing that I have learned over the years is to choose dresses that last season after season. Prioritizing quality over quantity is always my motto. If you have a great timeless dress that flatters your figure, just change it up with accessories and maybe even your hair for the evening. Most likely you won’t see the same people at every event, and even if you do, they won’t remember what you wore.

Here are four styles of cocktail dresses women over 50 that work for us. You just have to figure out which style flatters your body and makes you feel the best, and then I will give you some great styling tips for each of them.

The Fit-and-Flare Dress

Serious About Styling | SAS For Short shares a blue fit-and-flare dress which is one of the Cocktail Dresses For Women Over 50
Dress

The fit and flare dress works to define the waist, balance proportions, and always feels feminine. It is a great dress style for women who have hourglass and pear-shaped figures. This style looks best when it hits at the knee or midi length. You can find this classic style sleeveless, with cap sleeves, and short sleeves. Subtle prints or solids are always attractive fabrics for this dress style.

The dress in the photo above is a favorite of mine. Adreanna Pappel makes this dress season after season in classic black and several bold colors. You can wear it for multiple occasions easily by changing up your accessories for the season. In cooler months, make sure you have a beautiful wrap with you to add a little more personality while staying warm.

Here are a few other fit and flare cocktail dresses that caught my eye.

The Sheath Dress

Serious About Styling | SAS For Short shares a black sheath dress which is one of the Cocktail Dresses For Women Over 50

A classic sheath dress is just that….classic and timeless. This elegant style will always wow because it elongates the silhouette. This dress style is great for petites and for rectangular body types. When shopping for a classic sheath dress, look for a high-quality fabric that has a bit of stretch to it. That bit of stretch will ensure that you are comfortable in the dress so you can have a great time.

The sheath dress above is call the Jackie O and I am sure you could picture her wearing it. The dress also comes in a cap-sleeve version. I know many women in their 50s and beyond like to have a little sleeve coverage.

Here are some other great options for a classic sheath dress for your soirees.

The Wrap DRess

Serious About Styling | SAS For Short shares a photo of a woman wearing a wrap dress
Dress

The wrap dress, or a dress with rouching that looks like a wrap dress, is another flattering silhouette. It will flatter your bust, tummy, and hips. This dress style works well for most body shapes, especially apple and curvier figures. If you notice the wrapping on this particular dress draws your eye up.

This wrap/faux wrap style dress comes in various lengths and sleeve lengths. Just make sure that it hits you correctly at the waist for the most flattering fit.

The A-Line or Empire Waist Dress

Serious About Styling | SAS For Short shares a photo of a woman wearing an S-line dress
Dress

A-line dresses or empire waist dresses are very comfortable and can be very forgiving. This dress style tends not to be clingy. They work great for busty or pear-shaped figures. Look for fabrics with texture and sleeve details for extra visual interest.

Serious About Styling | SAS For Short shares a pink dress which is one of the Cocktail Dresses For Women Over 50
Dress | Pumps

How To Choose A Cocktail Dress For Women Over 50

One of the things I like most about aging gracefully is that I know myself. I know what makes me feel good and confident when I walk into a room. A dress that enhances how I look and aligns with my personality. That is something that each of us should look for when we are choosing a great cocktail dress.

Several years ago, a stylist friend reminded me that this is what I should ask myself when trying on clothing. When you walk into a room, is everyone going to see your dress, or are they going to see how great you look in the dress? So here are my tips for finding the perfect cocktail dresses fow women over 50 and then you can ask yourself THE question.

Think About The Event

Here are a few questions to keep in mind. Does the invitation include a dress code? Is the event you are shopping for formal or more relaxed? Is it indoors or outdoors? Will there be dancing? How long will you be standing, or will you be able to sit at times?

Consider your body shape

Whether we like to admit it or not, as we age, our bodies evolve. We need to make sure that we highlight our assets and make sure our dresses skim over the areas we don’t like as much. There is nothing better than a cocktail dress that flatters your figure for a boose of confidence.

Prioritize fabric and fit

So many times, as a petite, I have to shop for regular-sized cocktail dresses. So when it comes to fabrics, I always look for structured fabrics that hold their shape without being stiff. Also, I make sure that the dress can easily be altered. You always want to make sure that the dress fits well on the shoulders and bust. Tailoring the waist, hips, or length is an easier alteration.

Stay true to your personal style

There’s a cocktail dress out there for every style—classic, modern, romantic, boho. You want to feel like yourself in this type of special occasion dress so that you can enjoy the event and everyone sees YOU looking fabulous and confident in the dress.

Serious About Styling | SAS For Short shares a photo of her wearing a black cocktail dress
Dress

How To Style A Cocktail Dress For Women Over 50

Now, let’s style some cocktail dresses like a pro. There are four things that we need to complete our looks.

  • Comfortable shoes
  • Jewelry that enhances
  • A clutch or small handbag
  • Layer to keep warm. My preference is to always have a light wrap that complements the dress. This wrap comes in so many colors and works like a charm.

Fit and Flare Cocktail Dress Outfit

A fit and flare dress gives off a feminine vibe. That is why I like to pair it with strappy sandals and a clutch that has a little bling. The beauty of a navy dress is that you can pair it with gold or silver.

Serious About Styling | SAS For Short shares a collage of a blue fit-and-flare dress and accessories
Earrings (L) | Handbag (L) | Sandals (L) | Dress | Earrings (R) | Handbag (R) | Sandals (R)

Sheath Dress Cocktail Dress Outfit

This look is a bit more conservative. It would be appropriate for a business event.

Serious About Styling | SAS For Short shares a collage of sheath dress with accessories
Handbag (L) | Slingback (L) Dress | Earrings | Handbag (R) | Slingback (R)

Wrap Dress Outfit

A wrap dress or a dress that has ruching so that it looks like a wrap dress is a great optical illusion. I like the dress in this collage because not only does it have a beautiful neckline that draws the attention up to your face, but the fabric draping and waistline detail do the same. This is a dressier look, but getting a dress like this in a color that looks fabulous on you will last you for years and you will feel great every time you put it on.

Serious About Styling | SAS For Short shares a collage of blue wrap dress with accessories
Earrings (L) | Handbag (L) | Sandals (L) | Necklace | Dress | Earrings (R) | Handbag (R) | Sandals (R)

A-Line Dress Outfit

A-line dresses or Empire waist dresses are quite easy to find. Many women love to wear this style because it is forgiving and flattering. I like this dress because the fabric has not only pretty, feminine colors, but also because of its texture. A pretty jacquard fabric is hard to beat.

Serious About Styling | SAS For Short shares a collage of a floral dress with accessories
Earrings (L) | Handbag (L) | Sandals (L) | Dress | Earrings (R) | Handbag (R) | Sandals (R)

Thanks, Let’s Keep In Touch

Thanks so much for stopping by. Have fun shopping for a cocktail dress. Remember that you want something that fits you and your personality. We want to feel great in our choice so we can enjoy the soiree. Let me know your favorite cocktail dress style in the comments section below. If you are petite and over 50, you should check out my top 10 places to shop for clothes.

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