Dresses for Women Over 50

Spring Dresses

Dresses are one of the most versatile pieces of clothing to wear, for ease, comfort and self-expression. That doesn’t mean every stylish dress on the rack is perfect for every age.

While wearing something “too young” for your age can be a misstep, wearing pieces that scream “I’m over 50 and therefore dead to fashion,” isn’t the answer either. Experiment with today’s trends, keeping your favorite staples modern and fresh, and whatever you do, don’t toss out your body shapers! There’s no reason to say goodbye to great fashion just because your post-baby-belly isn’t rock-hard abs.

The merry-go-round of rotating trends brings back retro styles from just about every decade past. Use this to your advantage, pull inspirations from your favorite fashion-chapters past, and then push the age envelop to redefine what is appropriate for your closet. With an updated rulebook, dresses for women over 50 are aplenty.

 Your experience in fashion, as in life, will guide you away from many mistakes made by 20-somethings.

The current rulebook for fashion after 50 demands sleeves, longer hemlines and less bare skin. That, however, can become a recipe for a boring closet fast. So instead, let’s talk about how to safely break the rulebook, like Michelle Obama broke twitter in 2008 with her insistence on one-shoulder designs, *gasp*!

When you examine yourself in the mirror, are there any of these axioms that simply don’t apply to you, but instead feel forced by tradition? Let’s examine these perceptions on stylish dresses for the 50+ woman, and find a way around dating yourself by adhering to a rule that doesn’t apply.

Don’t show too much skin: Perhaps you’ve spent a small fortune on skincare, or always take the stairs instead of the elevator….why not showcase all the effort you’ve taken to preserve your great legs, or voluptuous décolletage? Choose your favorite skin to flaunt that feature. For example, a woman’s back is invariably one of her most alluring features, yet easily forgotten simply because it goes unseen in the mirror.

Sleeves-all seasons, all day long: Why force a sleeve when you can have an excuse to accessorize!? A sleeveless shift dress can be worn over a long-sleeved mesh bodysuit to add a personalized flair to the arms, disguise any imperfections and be body-slimming in one simple step. Add a ¾ sleeve bolero jacket, with the mesh sleeve peaking out and you’ve added a sexy flair and warmth in a very unique-to-you way. That’s only a couple of the many ways you can rethink the sleeve by thinking outside of the rule-box.

Length: Creative layering including hosiery, palazzo-pants or leggings can disguise any flaws. That will add another option to mix-and-match your favorite staples while allowing for shorter hemlines. Plus, accessorizing a short skirt in this way extends the visual length of your legs, especially when forgoing the heels. Otherwise, there are plenty of stylish dresses in today’s trends that allow for a longer skirt, like maxi or wrap dresses.

While we break those rules above, let’s consider a few new ones that are often unsaid.

Choose your prints wisely: So often I see a print on a friend and think, “Even my grandmother wouldn’t wear that!” Quite often it is a floral print in some predictable, dusty Victorian-era color scheme. Yes, it’s a lovely color-scheme. Yes, roses are quite nice. They should have never been combined on anything other than a wallpaper in 1886. When you choose your floral patterns opt for bright, cheerful colors and a more fun or artistic interpretation of flowers than the literal, painterly stalwarts.

Choose your fabrics wisely: Lace is lovely. Every woman should have a bevy of beautifully feminine, lace…lingerie. yes, women over 50 should absolutely own several pieces of racy lace undergarments. It’s good for the soul. Many dresses incorporate lace in all the wrong ways, as an easy way to cross off the ‘over-50 design-checklist.’ Instead of the matronly ‘mother of the bride’ floral-based lace designs, opt for a lace with a modern, geometric aesthetic. The lines lengthen and slim any area where the lace is applied.

As you can see, with a little creative thinking, it can be easy and fun to throw caution to the wind, just so long as you know which way the wind is blowing! Below you’ll find a selection stylish dresses for women over 50 handpicked for your closet.


Escada Divisu Floral Print Shift Dress

Escada, Divisu Floral Print Shift Dress, $1,395

Lela Rose Flower Button Boatneck Sheath Dress

Lela Rose, Flower Button Boatneck Sheath Dress, $1,290

Chiara Boni La Petite Robe Egea Floral Ruffle Sheath Dress

Chiara Boni, La Petite Robe Egea Floral Ruffle Sheath Dress, $700

DVF Lily Cinch Sleeve Midi Dress


DVF, Lily Cinch Sleeve Midi Dress, $498

Lafayette 148 New York Ensley Boatneck Shift Dress

Lafayette 148 New York Ensley Boatneck Shift Dress, $498

Swirl Print Dress

Reiss, Swirl Print Dress, $425

Sea Pia Floral Wrap Dress

Sea Pia Floral Wrap Dress, $365

Wrap Front Midi Dress

Reiss, Marlig Wrap-front Dress, $345

Elie Tahari Heidi Lace Eyelet Hem A-Line Dress

Elie Tahari Heidi Lace Eyelet Hem A-Line Dress, $298

LAcademie Tuscy Dress

L’Academie, Tuscy Dress, $198

Gal Meets Glam Edith City Crepe Fit & Flare Midi Dress

Gal Meets Glam, Edith City Crepe Fit & Flare Midi Dress, $178

Anthropologie Elm Collared Dress

Anthropologie Elm Collared Dress, $170

Arno Textured Shirtdress

Arno Textured Shirtdress, $150

Eileen Fisher Stretch Organic Cotton Tee Dress Color

Eileen Fisher, Stretch Organic Cotton Tee Dress, $125

Anthropologie Waisted Cupro Dress

Anthropologie, Waisted Cupro Dress, $98

Chelsea 28 Faux Wrap Tank Dress

Chelsea28  Faux Wrap Tank Dress, $88

Wayf Blouson Midi Dress

Wayf, Blouson Midi Dress, $69

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