The New Rules for Dressing In Your 50s in 2024

It’s getting real, ladies. I know that I felt like I was kind of cruising along, minding my own business, and then bam! 50 hit and I felt like everything changed overnight. Maybe it wasn’t 50 for you. Maybe it was 52, or 55, or 57, but I think that most of us get to a point sometime in our 50s where things seem to shift, and what worked before just seems to stop working.

So what do we do? We reevaluate, reassess, and move forward with the confidence that comes from understanding our silhouettes, embracing our best colors and owning our personal style. I polled the fabulous 50-something women in my Ageless Style Community, and heard so many varied and helpful perspectives on style in our 50s. And, of course, I add to the conversation with some tips of my own.

I’ve identified some style staples and tried and true pieces that my clients and other ASC members have relied on, and put them all in this 50s catalog.

50s Stores

As you’ll see from the comments below, the list of stores we shop at in our 50s is long, but some of the names that came up most frequently include Loft, White House Black Market, Talbots, Chico’s, Quince, and J. Crew.

Highlights & Challenges

The 50s often brings with it a bit more money and more time, along with a greater acceptance of our personal style and lifestyle. Cons, however, can include many of the same things (more money and more time leading to more choices and overshopping), as well as the changes that come with menopause. Many women also find that they are not as intrigued by the options in stores.

Elevate Your Everyday Outfits

Upgrading your style doesn’t need to be hard. Looking better can be as simple as upgrading and updating a single element in your go-to look. Rather than thinking that a style update involves going from jeans and a t-shirt to silk and pearls, and then they give up because the upgrade doesn’t suit their lifestyle. Instead, ask yourself how you can make your regular go-to outfits cuter. Instead of a baggy t-shirt and leggings, for example, try the same leggings with a button-front top and make sure your shoes are cute. Little tweaks, often in the styling, the fabrics, or the accessories, can be all it takes to love your look again.

Start Thinking Long-Term

Rather than relying on the quick hit that comes from buying a fun find on sale at Marshalls, put that money aside instead and splurge on a piece you will have for years. A fabulous linen blazer, a chic but comfortable pair of shoes, or the perfect pair of jeans are all worth investing a little more.

Invest in Undergarments

There has never been a better time to start paying attention to what you wear under your clothes than in your 50s. Consider buying shapewear a size or two up just for a smoothing effect under clothing, and getting a bra fitting every year. Invest in a good quality bra and it will elevate (literally) all of your outfits.

Put Fast Fashion In Its Place

Fast fashion is fine for the occasional fun trend find or the basic tee, but consider upgrading your core wardrobe pieces from brands that offer a little more quality, elegance, and attention to detail. Buy less, buy better should definitely be our fashion philosophy in our 50s.

Play Up Your Favorite Parts

Whether you love your legs or your eyes or your hair, maximizing your favorite parts can boost confidence and help you love the way that you look. When we shift the focus away from hiding the things we don’t love and put it towards highlighting the parts that we do love, our perspective shifts.

Learn to Layer

Layering artfully is a skill worth mastering, as the right layering piece can make you look longer, leaner, and more stylish. A dark or contrasting layer over a monochromatic base outfit is a shortcut to a stylish and flattering look.

Shop Contemporary Brands Not Mature Brands

The older we get, the more we should stay away from the over 50 brands. It makes sense if you think about it. Why, when we most want to look modern, chic, and stylish would we invest in brands designed to do the opposite? It just doesn’t make sense. Try shopping at a more modern store that has the same general style. Instead of Talbots, for example, shop Loft or J. Crew. Instead of Chico’s, try Anthropologie. Instead of J. Jill, shop Garnet Hill or Jenni Kayne.

The Fab 50s Ladies

I polled the women in their 50s in my Ageless Style Community, and here is what they had to say about style in this decade.

Ashley

“I used to work for WHBM, but now I feel that it is mostly workwear. I am semi-retired and want more usual, comfortable, cool clothes now! I shop at Loft, WHBM, Chicos, and Talbots – mostly from thrift or consignment stores.”

Tanya

I am 50 and love shopping in small boutique shops. Most of my clothes are from Colombia or Brazil, since I live in Panama. When I am in Florida, I always love stopping by WHBM to buy jeans and tops. I also love buying unique pieces from Trina Turk and Lilly Pulitzer.

Sara

I shop less at Costco and Old Navy. I shop more online: Quince, Nordstrom Rack, Amazon and try on at home and return what doesn’t work I have become much more picky about my clothes and my purchases. If it’s not great it goes back. I don’t want anymore clothes that just hang in my closet. Thanks to Nada Manley. I’ve learned so much about how to dress in a way that helps me feel comfortable and confident. 

Cathy

My go-to stores are Ann Taylor, J Crew, Madewell and I fill in with Loft and J Crew Factory. I’m more intentional with my shopping these days. Historically I’d buy a lot of items primarily because they were on sale. It has taken me far too long to realize that I’m not actually getting a bargain if the tags are still on.

Shannon

Current favorite places to shop: Loft. Quince. J. Crew. Heart of Haute (vintage-inspired clothing). I am working on not buying as much, buying better things, keep on learning what suits me best, what suits my lifestyle and climate. I can’t think of anything I don’t love about shopping in this decade but the amount of stuff out there and going through it to find the right things can be overwhelming.

Sarah

Yes. I shop primarily on Ebay and thrift stores. I love the thrill of finding a good deal. I don’t make a lot of money so it’s a great way of finding higher quality items without going into debt.

Mathilda

Turned 50 in December, actually don’t know where to shop 

Becky

“I will turn 57 next month. I shop at lower to mid-price retailers like Target, Walmart, Amazon, and even Aldi. I also love Lands’ End. I lost some weight last year, which I hope to continue this summer. And now that my 3 kids are grown and I’m no longer working full time I can focus more on my style. I love the current focus in fashion on ladylike elegance. I don’t love how hard it is to find a good fit, particularly in sleeve and pants length- I’m only 4’11.75”.”

Kristine

58 in a week. I shop outdoor sites for my personal life because I’m an outdoors woman. For work and evenings I like Everlane, Petite Studio, Banana Republic, Abercrombie, J Crew, Chicos, etc. today I have on SDeer pants that I love. They are cropped style but on me they’re full-length.

Kimberly

I’m 51 & get asked often where I shop & it’s everywhere! LOL I am finding that I’m gravitating away from the retail box stores though—only will shop there for basics. I love the variety (and deals) at Marshall’s & Ross so I frequent those places most… 

Wendy

Don’t like how most people nowadays dress frumpy, how it’s so hard to go into a store and find something that fits. How there are no set rules as to what you can wear and not wear at a certain age. I sometimes seem to be more dressed than the rest of the group. I am coming to find out that it is part of my personality to look put together but not overdone.

Susan

Shop at Kohl’s, Macy’s, Lands End, Lee/Wrangler factory outlet, and occasionally at LLBean.

Change: In the beginning of the decade, all my clothing money was spent for my children and almost none for me. Requests for Vineyard Vines clothing for them ate up the budget. Some of my shirts and sweaters are 20–30 years old.Now, at the end of the decade, my adult children can buy their own clothes, and I can finally buy some pieces for myself. My weight has fluctuated up and down by 60 pounds. I treated myself to more clothing when my weight was down than I do when my weight is up.

Love/hate: My boss used to be the best dresser at the plant. Now that she’s retired, I’m the best dressed woman in the plant. I like maintaining a minimum standard. I hate that some of the younger employees come to work in ripped jeans or sweat pants and slouchy sweatshirts.

Geanna

I don’t really shop…at least not yet.

Like Susan, I spent most of my clothing budget on my children (we have 5) and hardly any on myself. Most of my clothes are 15–20 years old. Now that the youngest is ‘somewhat’ grown, I can finally focus on my wardrobe and invest in some quality pieces for myself. My weight has fluctuated up and down by 60+ pounds (down 40+ now), so I am focused on understanding why and working on that before making clothing purchases. Also, I want to learn as much as I can about who I am in this phase of my life and what I want that to look like.

I have a love/hate relationship with today’s fashion trends. I love the freedom people have to express themselves, but I also feel that some people don’t make much of an effort, and it shows.

What are your thoughts on style in your 50s? And how can we make this our most stylish decade ever? Let’s discuss in the comments!