The Most Flattering Dress Styles for Women Over 50

Six to Sunday

Dresses. The ultimate one-and-done. Little effort, big impact. Pieces that can take you from season to season with just a few minor tweaks.

While still in the throes of summer, airy dresses are our favorite pick to combat that collision of outer heat and inner heat (hot flashes, anyone?)!  But finding the right dress - the one that makes you want to twirl - can take the ease out of the piece.

To help navigate the options, we’ve simplified the search with three top styles for your wardrobe: a fitted pick, a classic shape and something more relaxed and cooler. Our criteria? Each look must work well on many body shapes and be versatile for styling.

Maybe you like to stay in your lane. Or maybe you want to step out of your comfort zone and play with new silhouettes. After all, this is what we love about midlife and midlife fashion: a time to meet yourself where you are or to reimagine your world…and wardrobe!

As far as we’re concerned, the only real rule is that you feel confident and comfortable in whatever style you choose. Because when you step out feeling great in what you’re wearing, you radiate all of the good stuff - energy, attitude, and life!

Check out our picks below, and get ready to share where you found the piece!

A great dress can make you remember what is beautiful about life. - Rachel Roy

Our Fitted Pick: The Slip Dress

Hands down, we think the slip dress is the winner in this category. It’s incredibly versatile and can be worn on its own or layered, dressed up or down. For summer, style with a kitten heel or flat sandal and transition to fall with boots and a leather or jean jacket. It comes in a variety of lengths, fabrics and price points, and looks good on everyone when the fit is right. Look for styles that skim your shape - not too tight nor too loose - and for optimal versatility find a length that falls 3-6 inches below the knee.

Three photos of women in slip dresses

Our Classic Pick: The Wrap Dress

Nothing says classic like a wrap dress. Why do we like it so much? For starters, the wrap dress V-neck cut and waistline make it an amazingly flattering silhouette for all shapes, while the fabric can be bloused or smoothed based on your preference of wear. Moreover, the classic shape allows you to be playful in print, making for an easy transition from office to a night out! Due to its great versatility, we say: invest in a good one. Opt for a simple, clean-line version like the iconic DVF dress that started it all or try one with a twist, like a ruffled sleeve or high/low hem.

Three photos of women in wrap dresses

Our “Keep it Cool” Pick: The Kaftan

Sometimes you want as little as possible hugging your frame, especially when the heat is on!  And we’ll just say it, midlife shape-shifting can feel frustrating, so why not pick a beautiful swath of fabric, and make your life easy with a loose shape and an instant mood-lifter! And for the times you want to offset the volume, grab a simple wide belt. It’s like having two dresses in one! Here’s to beautiful and cool all summer long.

Three women in kaftan-style dresses

Which is your favorite pick for summer time dress picks? Share your thoughts in comments below!

Six to Sunday
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