Today’s guide to cocktail dresses for women over 50 was written by style expert Adrea Pflaumer. You’ll learn what’s appropriate for what occasion and what will suit your body type (spoiler, this doesn’t necessarily have to be a dress!). So put on your red lipstick and get ready to step out in cocktail attire with confidence!

*Affiliate Disclosure

When it comes to choosing what to wear to an event as a woman over 50, this article will go over everything worth considering—let’s start with the history of the cocktail dress. The concept of a “cocktail party” was a popular convention that began around the ’50s. These were often gatherings for business associates and their spouses for the purpose of making connections and impressions. Attendees dressed in sophisticated and understated attire. 

Hence, the “cocktail dress” was born. As was popular at the time, these were mostly simple silhouetted knee-length frocks made of more upscale fabrics. But today, the “cocktail dress” has come to signify something that can be appropriate for a number of different occasions, like a sophisticated St. Patrick’s Day Cocktail Party, from fairly formal to more casual, from date nights to weddings. 

For more expert tips from Andrea, you’ll love this article on the best colors to wear with gray hair! And be sure to check out Honey’s Must-Haves for Summer 2023!

What’s Cocktail Attire for Women?

Choosing the right dress depends on the time of day, time of year, and the purpose of the event. And yes, it depends upon the age of the attendees. The way a lot of younger women dress these days is very different from how we might dress. Does that sound ageist? Well, it’s pertinent. You’re going to find a lot of pretty revealing attire among a younger crowd these days.

For us, there’s that fine line between, “if you’ve got it flaunt it” and “trying too hard.” (Martha Stewart’s recent swimsuit spread for Sports Illustrated walked that line. The comments on social media fell solely into two camps: “ewwww,” and “you go girl!”) 

I guess the answer lies in how confident you feel about your body and your “look.” Confidence is a badge that carries us through a lot of forbidden territory. Still, we convey confidence when tastefulness prevails. And good taste shows that you have aesthetic sense…and common sense. So, let’s consider how to dress for different kinds of cocktail parties that show you have both. And then, we’ll look at the colors and styles that might work best for your body shape.

Cocktail Attire for Women After 50: 5 Things to Consider

#1 Level of Formality for the Event

When you aren’t sure what the expected attire will be, go ahead and ask. Your host will appreciate that you didn’t create a spectacle by showing up in khakis or a ball gown.

If you receive a printed invitation, plan to dress up. That might mean wearing something like a nicer date-night dress, or simply a combination of feminine tailored slacks with a satin blouse or top and jacket. The latter is a perfectly acceptable alternative to a dress and right now there are gorgeous silk satin tops and blouses available in a lot of yummy colors.

Whether you wear a dress or slacks pair them with lower heels or dressy sandals because you’re likely to be standing for a while. If you wear sandals, keep them simple and elegant. This is not a time or place for gladiator heels. 

If you receive an email that reads, 

“Hey, Sarah, come join us for a little cocktail party at our place this Saturday at 3:00. We’re inviting the usual suspects, and we’d love you to come.” 

…you have a lot more latitude. But still, ask the host how formal or informal the event is going to be. If you ask, “is there anything I can bring” and the answer is “sure, how about your famous artichoke dip,” that tells you it’s going to be pretty informal. You can probably wear a more casual dress. You’re just not going to show up in an LBD with pearls. 

If it’s more like, 

“Tabitha was just nominated to the National Honor Society, and we’re throwing her a cocktail party this Saturday at 5:00 before she heads off for her summer internship in DC…” 

…expect to dress up more. It’s a sign of respect and acknowledgment of an achievement. That means, don’t show up in jeans, even if you have seen Tabitha wear them to school all year. This doesn’t sound like a highly formal event, unless your friends tend toward formality. But still, a pairing of matching or separates, or a simple sheath-type dress with lower heels or flats will do just fine. Keep it low-key. Tabitha should be the center of attention, not you.

#2 Time of Day/Time of Year

If the party is a daytime event, especially if it’s outdoors, you have a wider choice of textiles (more on that below). Also, it goes without saying, consider the weather. Warm summer outdoor cocktail parties are an opportunity to show off your tanned shoulders and toned arms if you want to go sleeveless or off-the-shoulder. And yes, we can wear off-the-shoulder tops and dresses at our age. The better part of common sense just suggests avoiding the ones with deep plunging necklines.

Midi dresses – floral, solid colors, tiered – in lighter-weight fabrics like cotton, gauze, and knits are everywhere now, and they are perfect for an outdoor daytime cocktail party. Wear them with your gold or silver sandals, flats, low heels or higher, unless the party is held on soft dirt or sand. Although sneakers are being worn with everything these days, you aren’t likely going to see them worn with a midi dress at a cocktail party.

If you’re more of a slouchy slacks type, one of the new eyelet-type blouses with soft-textile wide leg pants will work just as well. If either your blouse or dress has a lot of color or more eye-catching style (as would an eyelet blouse) keep your jewelry simple. A pair of the smaller chunkier hoops that are very popular now is a nice complement to both dresses and pants outfits.

#3 Textiles

This is the year of see-through: crochet and eyelet. Both were considered passe not that long ago but have just exploded onto the spring market. Eyelet carries a feeling of freshness and youthfulness. It’s a nice option for a daytime event in lighter colors. But it can also work nicely in black for evening cocktail party type events. Crochet is one of those weaves that a lot of younger women have embraced. If a dress comes with a matching slip dress underneath, it can be more appropriate for women our age. You’ll see many with a lining up to just above the knees, with no lining on the rest of the skirt.  

Everyone loves wearing linen once the weather turns warm. But unless you never use a seat belt, expect that linen wrinkles five minutes off the hanger. Heavier weight linens will resist this problem a little more than lighter linen weaves. And black, navy, or white linen will camouflage those wrinkles more than one with brighter colors and prints. 

Since midi and ankle-length dresses are extremely popular right now, it’s a good bet that for the holidays we’ll be seeing this trend continue, likely in the more winter-type fabrics like velvets, heavy satins, but also in softer knits and fine chiffon pleats. 

But now and likely in the fall you’ll also be seeing many variations of the Jean Harlow-type satin slip-type dress. Some are trimmed with lace and frankly, simply look like lingerie. (The marketing hype is that “every French woman owns one.”) Unless a woman over about 65 has extraordinarily toned upper arms and is very fit, I have yet to find one who can get away with such a dress. Prove me wrong. But you can certainly pair a satin blouse with tuxedo pants or wider-leg pants for a cocktail party. If you wear a satin slip skirt, however, which will cause less commotion than a full slip dress, wear it with a bejeweled or sequined sweater. That’s another cocktail “look” and will be a perennial outfit that can serve you for years to come.

Except for afternoon, warm-weather cocktail parties, avoid gauze, nubby weaves, or stiff cotton. They read as very casual. You would likely feel a bit underdressed. One exception would be a polished cotton Carolina Herrera-type blouse worn with a pencil or midi skirt and bolder jewelry.

#4 Color

Once you know what the level of formality and venue of the garden or cocktail party it comes down to color, style, and body shape. Let’s start with color. (Read more about this topic in my story, Colors That Heal Us.)

Neutrals

You can’t really go wrong with a black cocktail dress for a woman over 50. It speaks of sophistication, elegance, and understatement. Think of Audrey Hepburn’s LBD in Breakfast at Tiffany’s. Black is, of course, also very slimming. If you are concerned about a few extra pounds here and there, it’s kind of a no-brainer choice for cocktail party attire. 

If you love a black dress and like me don’t look great in black, just up the intensity level of your foundation, blusher, and lipstick. That can mitigate a lot of skin tone concerns.

And then, there’s white, or ecru, or tan, or khaki. White is a more upbeat, “forward” choice than the others. It connotes purity if that’s what you’re going for. Ecru, tan and khaki (the latter would only be suitable for a more informal daytime affair) are variations but have the same psychological effect. Those other shades, which contain some mix of yellow and black, are more conservative neutrals. You won’t stand out as much as you would in white. But they might suit your skin tones better, creating a very harmonious look. And harmony is always a good choice for any look.

The Color Spectrum

Reds — in all shades from deep scarlet to brick red —are simply intrinsically feminine and romantic. Red is the color that vibrates highest on the light spectrometer. It conveys energy and sensuality. In its lighter versions (the pink and peach range) it is fresh and less intimidating. If you want to convey any of those qualities and you expect that the other guests will be wearing more showy attire, red is your color. Being old-fashioned, I still wouldn’t recommend a red cocktail dress for a wedding. Pink, sure, go ahead.

There are blues, and then there are blues. What a navy cocktail dress expresses can be very different from what a sky-blue dress conveys. In general, all blue shades carry some element of power. Surprised? Well, navy says, “I am in charge.” A vivid sky blue says, “I am bright and energetic.” Pretty much anything in-between is an adaptable choice for a cocktail dress.

Green speaks of the earth, new beginnings, and growth. That makes it a very good option for events like graduations and even weddings! 

Lastly, yellow is a wonderful color to demonstrate cheerfulness and positivity. It’s a terrific choice for a summer gathering, especially in print. And you will definitely get noticed … because it will cheer up everyone else.

Our Memories… Our Clothes

#5 Style and Body Shape

But frankly, there is only one rule of thumb for a cocktail dress that must be observed, and it applies to all your wardrobe choices: eliminate the negative, emphasize the positive. For example, if above-the-knee balloon skirt printed dresses are all the rage right now (they aren’t but it’s an exaggeration to prove the point) but you have chunky or less-than-shapely legs, resist the temptation. Whatever part of the body is emphasized, that is where the eye goes. So, if you don’t want to emphasize your hips, bust, shoulders or waist, don’t wear something that has a clear demarcation line there: hemline, sleeve length, seams, gathers, darts, and patterns. 

And it should go without saying, but a good tailor is your best friend. (As a petite, I’m likely paying off my tailor’s mortgage.) A good tailor will tell you honestly where your dress should be hemmed and how long the sleeve should be.

Now, bodies tend to fall into sometimes unflatteringly-named shapes: Apple (for someone with a larger middle), Inverted Triangle (for someone with broader shoulders and narrow waist and hips,)  Rectangle (someone with similar width shoulders, waist, and hips,) Hourglass (has similar sized shoulders and hips, with a narrow waist,) and Pear (for those whose hips are the widest point on their body.) But they do tell a descriptive story, so we’ll use those labels. 

Actually, a lot of us have bodies that are combinations of these categories, especially as we gain or lose weight. So, let’s look at some of the popular styles around right now and describe which body types they work best for. If you straddle more than one shape, consider the recommendations for both.

Choosing From Garden Cocktail Attire or Resort Cocktail Attire for Women Over 50—Fit and Cut

Sheath dresses: 

Many women – especially those with rectangle, hourglass, or inverted triangle bodies can look sophisticated and elegant in a sheath. The V-neck, ¾ sleeve sheaths are especially flattering. 

If you have broad shoulders just avoid boatneck or off-the-shoulder styles. 

But if you are carrying a noticeable amount of weight in your bottom and hips, this probably isn’t your best choice. It tends to pull awkwardly around your bum, regardless of its cut or textile. But the next option is.

Fit-and-flare: 

The original 1950’s cocktail dresses were often in this style. The bodice was fitted, the sleeves were often ¾ length, and the skirt was either gathered or seamed to flare out and skim over the hips. And they created a flattering waistline, making them a nice choice for women with Pear or  Apple shaped bodies. This is a very nice option too for Triangle shapes as it creates the illusion of curves.

If you’re more Hourglass shape this will simply echo and emphasize your body in a lovely way. A V-neck version will also elongate the look of your torso if you tend to carry weight in your bust line or have a short waist. If it has a higher waist, it will skim over and de-emphasize an Apple waist.

Halter, Choker, or Cross-over neckline: 

All of these are good options for an Inverted Triangle body as they draw attention to the face instead of the shoulders. They are also more flattering on women with smaller busts. The way they drape from the neck emphasizes the bust area can make them a less than optimal choice for a larger-busted woman. They will throw you off balance, visually, if you are a pear shape or Apple.

Off-the-Shoulder: 

This can be a lovely option for a pear-shaped body as it draws attention to the upper body and creates a wider look for the shoulders. A lot of women who are this body shape tend to have sloping shoulders but also long lovely arms. It’s a nice way to emphasize your arms. Any off-shoulder dress reveals the clavicle, which is a beautiful part of the body.

Wrap Dress: 

It’s simply universally flattering, which is why Dianne Furstenberg garnered millions of grateful fans by designing it. For a Rectangle it gives you shape. For a Pear it emphasizes your bust. For an Apple it emphasizes the bust and gives you a shapelier waist line. For an Inverted Triangle it draws attention to the waist, but look for one with a more flared skirt. A fitted skirt wrap dress will emphasize the size of your shoulders. And for an Hourglass it’s just a no-brainer. It emphasizes all your assets: bust, waist, and hips. 

Asymmetrical top or hem: 

If the bodice is one-shoulder or has an emphasizing detail at the shoulder it works similarly to an off-the-shoulder dress. That means it brings the eye up to the shoulder area, but because of the asymmetry, doesn’t emphasize the breadth of the shoulders as much. An asymmetrical or asymmetrically ruffled hemline, especially if the top is also, creates the illusion of an hourglass body. But it’s tricky. It will show off your shoulders and your legs, so be prepared to do that. But asymmetry at the hem will make your legs look longer.

Midi or Maxi: 

The only caveat here, as these are wildly popular right now, is to make sure they don’t end at the widest part of your leg if you have fuller lower legs. The hem can be either just above or just below that area and will de-emphasize the fact.

Final Considerations For Women Over 50 When Choosing a Cocktail Dress

One last point. The idea of a real cocktail party seemed to fade a bit during our baby-boomer and millennial child-rearing years. It was replaced with smaller and more intimate dinners with close friends, especially those who had kids. 

But that’s too bad, because throwing a cocktail party can be a very nice way to make new contacts and friendships, especially if you are new to an area, have just downsized, or have moved into a retirement community. It’s also just a great way to bring a mix of people together. Inviting guests from multiple generations and of varying interests keeps us youthful and engaged, and aware of new ideas, events, artists, and cultural trends. And, it’s a fun reason to dress up! Pour a glass of champagne and celebrate with your new friends.

Cheers!

About the author:

Andrea Pflaumer is the author of two books: the Amazon best-seller Shopping for the Real You: Ten Essential Steps to a Perfect Wardrobe for Every Woman: Fashionistas, Fashion-phobes, and the Over 50 and She’s Got Good Jeans – a guide for how to shop for and where to find the perfect jeans for your body and budget.

She does in-person and online wardrobe and shopping consultations for women worldwide and blogs at Shopping for the Real You. Her free course, Lazy Person’s Guide to a Perfect Wardrobe is available on GoHighbrow. Andrea hosts two video series: Vital, Vivacious, and Visible after 50 and Shopping for the Real You: Expert Edition. She interviews women in the areas of fashion, beauty, and wellness on her Shopping for the Real You YouTube channel. She is a regular contributor to several national and international publications for women over 50.

*Honey Good may receive a small commission for items purchased through links on this page. This helps with the cost of maintaining this site.

How to Dress a Plus-Size Body at Any Age!