Top 10 Dress Styles for Women Over 50

Editor's Note: This post was updated in June 2013. I've included prices with some dresses, but click on photo or text for best price now. Or check out current sales on my Bargains Now page.

Here’s my list of favorite flattering dress styles for women over 50. Of course, not all designs will be perfect for every over 50 body shape or every over 50 personality. But a few styles come pretty close to being universally wonderful for older women. I've tried to give a range of dresses, from casual to cocktails.

This post first appeared in May 2011. I asked readers to tell me which dress styles they liked and which they'd never wear. I've appreciated the feedback immensely. It's clear that women over 50 are longing for the fashion world to start showing apparel on older models of average weight. I wonder if that will ever happen. I hope so.

#1: SHEATH/SHIFT




The sheath or shift is so simple and sophisticated. I know, I know--a lot of over 50 women wouldn't be caught outside their homes in sleeveless. I truly appreciate that. But plenty of women over 50, like my 53-year-old girlfriend pictured above, still wear sleeveless, especially in the summer and for evenings out. Anna Wintour, 63, looked fabulous in sleeveless and cap sleeve dresses in the documentary, September Issue (2009). Although...she often wears a lightweight cardigan, sometimes just draping it over her shoulders. I'm a huge fan of lightweight cardigans!


Where to Shop...
Where to shop for a sleeveless sheath? Just about everywhere! My favorite sheaths for women over 50 have a print, like the floral print sheath my friend is wearing. A pattern is a great way to hide lumps or bumps. For example...

Jones New York ~ Jones New York Printed Boat Neck Dress (Black, Size 12), available in sizes 4-16($139).

~ Or if you prefer a solid, there's Jones New York Bright Sheath Dress (Orange, Size 12)available in sizes 4-16 ($99)

Land's End ~ I love anything with lace sleeves, so I'm crazy about this Women's Plus Size 3/4-sleeve Lace Ponté Dress - Classic Navy, 14W ($139.99)





# 2: THE WRAP
What makes the wrap dress ideal for just about every over 50 woman is the V-neck and draping above the waist, drawing attention away from the tummy and hips. My favorite wrap dresses have three-quarter sleeves and a print (to hide those little lumps and bumps). For instance, here I am in my Coldwater Creek wrap dress (photo below). The dress's skirt is lined, which helps it keep its shape. I got this in February, have worn it several times and love it!







Where to Shop...Shopbop ~ The wrap design was created by the Diane Von Furstenberg, one of my "woman of a certain age" icons. Her wraps are famous for their bold colors and prints. If you are looking to invest in a few garments, I can't think of a better an investment than one of her wraps, such as Diane von Furstenberg New Jeanne Two Dress (was $345, now $276).

Pure Collection ~ For a wrap dress under $200, take a peek at this Silk Jersey Wrap Dress (was $248, now $186 for Flattering50 readers)





There's also a lovely blue wrap from...

Ann Taylor ~ Cross Front Shirtdress ($128, now $108)


Jones New York ~ Jones New York 3/4 Sleeve Wrap Shirt Dress (Black, Size 12) ($128) Sizes 4-16.


#3: FULLER SKIRT
Dresses that are fitted on top and flare on bottom (ie, an A-line) are a flattering choice for most older women. They're also very comfortable.







Where to Shop... 
Land's End ~  Women's Regular 3/4-sleeve Drapey Ponté V-neck Dress - Black, M is another popular dress style right now.






Or for something in a different style, take a peek at a couple of other dresses with comfortable full skirts...

Pure Collection ~ Ultra Soft Jersey Dress (was $89,now $73.50 for Flattering50 readers) in trendy deep red.

Jones New York ~ Jones New York Floral Boat Neck Dress (Petite) (Blue, Size 12) available in Sizes 2-16 (was $139)


Willow Ridge ~ Here's a well-priced dress ($34.99). For details, click on the photo and then search "Dresses."




#4: COLOR BLOCK
I'm a huge fan of color block dresses for women over 50. Color block designs vary tremendously and some are more age appropriate than others. I'm partial to the ones with dark vertical panels on the sides because they make a woman look slimmer. Here's a photo of an over 50 friend in a black and trendy emerald green dress. My friend has nice thin legs, so she can wear a short dress with leggings, a black long sweater and fur-trimmed short boots.






Where to Shop...
Jones New York ~ I love the roomy skirt and eyelet panel on this Jones New York Belted Eyelet Dress (Orange, Size 12) ($149).





Ann Taylor ~ Here's a dramatic black and white Ann Taylor Colorblocked Sheath Dress ($128)




#5: V-NECKS
At 50+, I want to draw attention away from my jawline, which, sadly, is starting to sag. A V-neck dress offers a slight distraction and is very feminine for women over 50.  Above are two examples, one for day (left) and one for night. I can't imagine wearing either one without a pretty necklace. And depending on the fit, I might also add a thin belt to the purple dress.


Here I am in a jersey dress with a v-neck and an empire waist. It was feminine and ultra-comfortable for a recent dinner cruise on the Seine, celebrating my wedding anniversary.







Where to Shop...
There's a wide variety of dresses with V-necks, as I'm sure you can imagine.

Jones New York ~ There are wrap dresses, like Jones New York Lace 3/4 Sleeve Dress (Yellow, Size 12), available in sizes 2-16 ($139).


Land's End ~ Or a tie-waist dress, like Women's Regular Knit V-neck Tulip Dress - Fresh Grass, XL ($64) in sizes XS-XL.








#6: THE LITTLE BLACK DRESS
At our age, too much black may be too harsh or severe looking. Sometimes, but not always. I see plenty of over 50 women, like the one below, who look quite elegant in a basic black dress. And I love the 3/4 sleeves.








Where to Shop...
I have a sleeveless black sheath with black sequins that is a lifesaver when I have to pull together something for a dress-up occasion. I highly recommend a LBD--it solves so many "what to wear?" dilemmas.

Shabby Apple ~ If you prefer sleeves, take a peek at Frankie ($90)







~ Or take a peek at the Bette D. ( was $88, now $65 in Sizes L and XL).


Shopbop ~ Pencey Standard Drape Dress ($121) in sizes XS-L.




#7: SHIRT DRESS
Shirtwaist dresses are so retro! The structured design with belted waist is perfect for many over 50 figures. My only concern is making sure you don’t look too matronly or Newport-bound. Color, fabric, design and the right accessories will keep the shirtwaist from looking too frumpy. My khaki green shirt dress (below) came with a tie for the waist. But I like it much better with a leather belt. I wear the dress with a black camisole top, tights and tall black boots. I also like to wear it over my black skinny jeans and black booties.

Where to Shop...
Ann Klein ~ If you like the shirtwaist style, but don't want to look like an aging Preppy, a fun, sophisticated tropical print, like Anne Klein Palm Tree Print Belted Dress (Orange, Size MD) ($99) might be perfect.





Jones New York ~ Jones New York Relaxed Shirt Dress (Green, Size 16) ($79) in Sizes 4-16.

Pure Collection ~ Silk Linen Button Through Dress(was $188, now $144 for Flattering50 readers.)


#8: DRAPING
Draping is a great distraction, whether it's around the neckline or waist, or in the skirt. And it's so soft and feminine looking! Here's a Jones New York Side Drape Dress (Orange, Size 12) ($128) (Sizes 4-16 and in Green, too) that I'm just crazy about.









Where to Shop...
There's a lot of variation in the way a garment is draped. As a result, you'll find that some draping is great for daytime and other designs that are perfect for evening affairs.


Pure Collection ~ Silk Jersey Draped Neck Dress (was $248, now $186 for Flattering50 readers).



#9: SLEEVES
I’m not going to put a moratorium on sleeveless dresses now that I’m post-50. There are just too many beautiful sleeveless dresses for women over 50. But you can be sure I'm going to grab a well-designed dress with sleeves whenever I can. Finding a sophisticated dress with sleeves for evening activities can be pretty challenging. That's why I'm using this Jones New York Printed Dress (Blue, Size 12) ($128) with three-quarter sleeves as an example. The rhinestone brooch offers simple elegance, not over-the-top glitz. It's available in Sizes 2-16. Sorry about the skinny models!







However, with all pretty sleeveless spring dresses, I might just throw a little cardigan or jacket over my shoulders. I love, for instance, a suit dress combination like this Jones New York Tweed 2 Piece Dress (Black, Size 12) ($168) in sizes 4-16.





Where to Shop...
Shopbop ~ Here's a Diane von Furstenberg New Julian II Dress (was $365, now $292.00) in trendy black and white.

Jones New York ~ For a long sleeve dress you can wear to work or an afternoon wedding, I like... Jones New York Floral Dress (Blue, Size 10), available in sizes 2-16 ($134)



#10: FEMININE ACCENTS

I could write, and maybe I will, a whole post on feminine dress details—ruffles, peplum, light beading, lace, crepe or sheer fabrics, tiers, or ruching. As we age, it's important to continue to express our wonderful female energy, compassion and sensitivity in what do as well as what we wear.

Recently, the over 50 wife of a friend came to a party in a black loose dress with cut-out shoulders (like the one on the right, though you can't see the cut-out shoulders very well). I thought: "What a great solution to the aging arm dilemma." I love the dress on the left, too, and know several very trim over 50 women who would look fabulous in it. I'll stick with the loose and easy dress on the right.



Where to Shop...
Dress with a peplum waist are feminine and flattering for women over 50. Here's one from...

Ann Taylor ~ Pintucked Asymmetrical Peplum Dress ($98) in sizes up to Size 18.


For more dress styles, take a peek at Summer Sale On Dresses For Women Over 50. And...here's some links to shopping bags: