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What Are the Best Dresses for Older Women of Every Size and Shape?

By Stephen Hadley August 17, 2021 Beauty

Fashion should be – and is – for everyone. The idea that only the youngest, thinnest women deserve all the style attention is dead wrong. And thankfully, there are more options available to women of all ages, sizes, and shapes than ever before.

Even so, it can be so hard to find a great dress, especially if your tastes have matured as you’ve gotten older. You don’t want a boxy, severe dress that makes you look shapeless and masculine. But maybe you’re not thrilled about the short, low-cut dresses you tend to find in local stores.

The good news: you can look stunning in a dress that fits your personal style perfectly, no matter your age, size, or shape. Here’s how.

What to Look for

One of the major concerns for women over 50 is finding the right length. If you’re all about strutting your stuff in a shorter-length dress, go for it! But you may find that you feel most comfortable and confident in a slightly longer dress that’s still flattering and feminine.

If so, try a tea-length dress. Since the hem falls just below the knee, that length is versatile for everything from casual to formal.

Not thrilled about wearing sleeveless dresses but still want a clean, simple look? Try cap sleeves. They cover your shoulder but still show off your arms. Another great option is a ¾-sleeve dress. This flattering length provides coverage for your upper arm but still shows a bit off and is easy to accessorize.

What if you find the perfect sleeveless dress, but you were really looking for something with a bit more coverage? No problem! Wear that perfect dress with a casual or dressy jacket. A ¾-sleeve jacket over a gorgeous dress is a stunning look.

Beyond the cut and design of the garment, pay attention to the fabric it is made from. Easy care, easy wear fabrics ensure you don’t have to deal with frustrating washing instructions or frequent trips to the dry cleaner.

Fabric blends that include a bit of stretch are flattering for any body shape. A little stretchiness brings a beautiful drape that accentuates your figure in a dress that keeps its shape.

Define Your Signature Style

Before you find that perfect dress, think about your signature style. What do you love to wear? Which dress styles stand out to you when you see others wearing them?

Prefer an Understated, Simple Style? Or a Perfect Travel Dress?

Travelsmith has a beautiful selection of dresses in colorful cotton-blend knits for under $80.

Soft Surroundings doesn’t advertise as a travel wear site but has a lot of very wearable wash-and-wear maxi- and midi-length dresses in prints and solids for under $80, and they are a bit more fashion-forward in style.

Love Bold Looks That Make a Statement?

Try a wrap dress with a big, floral pattern or a vivid color. Wrap and faux wrap dresses were made popular by Diane von Furstenberg several decades ago and are another great option for older women. They have a flattering, feminine drape that works with most body shapes.

Make sure the neckline is comfortable and right for you. If you prefer a look with more coverage, go with a wrap dress with 3/4 sleeves.

A dress from Diane von Furstenberg can cost anywhere between $200 to $250. That’s not feasible for everyone, but there are several retailers that offer some great ones at more affordable prices.

Leota has a wide range of ¾-sleeve, knee-length wrap dresses, mostly prints, and some solids – all for around $100. Audrey Whitmore also specializes in wrap dresses that are price pointed at about $105.

Are You a Creative and Artsy Type?

Go for unique or vintage dress styles. One place to look is Etsy? The website features creators that sell their hand-made creations. Look for your perfect one-of-a-kind dress! You can specify whether you’re looking for handmade or vintage-type items… or actual vintage items. The prices vary wildly, but you can find some real deals here, sometimes made to order.

Are You a Vintage Fan?

If you love vintage styles – as in the 50s and 60s style, not as in resale shops – you might be surprised to find some of your favorite prints re-imagined again at ModCloth. They offer a full range of sizes and styles, but you have to scroll a bit for the long-sleeved dresses.

Want a Versatile Dress That Works in Formal and Casual Settings?

Get a flattering sleeveless dress that you can wear with a variety of jackets and cardigans.

How About the LBD?

The Little Black Dress should never be underestimated – for everyone from petite older women to plus size women over 50. Go with a slightly longer length – falling just below the knee – if you prefer. For more coverage and comfort, you could add a jacket or cardigan. An open-front kimono sleeve jacket can step a casual dress up to formal.

Enjoy the Versatility of a Beautiful Dress

The right dress can work for everything from lunch with friends to professional events. Don’t be hindered by what might seem like a lack of options. Identify your signature look and compare dress styles to find what’s right for you.

If you’re struggling to find the right plus size dress, consider boutique and handmade designers who work specifically in plus sizes.

Think Inside the Dress

An ill-fitted bra can make or break the look of your beautiful dress. When was the last time you got fitted? You can go to a specialized store, like Victoria’s Secret, to get fitted for the perfect size bra for you. You should think of doing this every time you have a weight fluctuation. Your breasts will be supported adequately in a well-fitted bra and your dress will automatically look better.

How do you determine whether a dress style is right for you? Do you have a favorite style? Which dresses make you feel most feminine in your 60s? Please share in the comments below.

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The Author

Stephen Hadley, founder of Generous Fashions, has been exclusively creating plus size clothing for women (XL to 4X) since 2002. He designs fabric and garments for and his Etsy shop, which offers Sixty and Me readers a 10% discount here Sign up for the Generous Fashions newsletter for new arrivals and member discounts.

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