style in your 40s, 50s, and 60s

How to Have Style in Your 40’s, 50’s, & Beyond

Please note that this post may contain affiliate links and any sales made through such links will reward us a small commission – at no extra cost for you.

It seems like the fashion world is specifically geared towards younger women and not very often (though more often now) would you see a woman over 40 in a fashion magazine. And I say that’s a real shame because even though I’m only in my mid-twenties, I’ve always admired and gathered inspiration from women who are older than me. For this post, I found some amazing women on Instagram (all over 40!) who so kindly sent me some of their favorite looks to use as examples on how to have style in your 40s, 50s, & beyond so you could be inspired too!

Wisdom generally comes with age and so does perfecting your style. These women have been around for many waves of trends and though they may pick and choose what they like from trends, their style is generally solidified and they are confident in who they are. They have a unique sense of style they’ve developed over time and it seems to always have the perfect mix of timeless yet stylish. How could you not be inspired by that?

How to Have Style in Your 40s, 50s, & Beyond

Add a twist to the classics

I love a basic black blazer as much as the next girl, but let’s say you’ve worn blazers for 30+ years already. You may be wondering how can you keep classics feeling stylish and not stale.

The answer? You’ve got to add a twist!

Let’s use the blazer example for instance. There are many things you can try to jazz up this classic.
Find one in an oversized fit or an extra-long length (like this one).
Roll up the sleeves so a pop of pattern peeks through (like this one).
Get one in a bold color (like this one).
Find one with an interesting print (like this one).
Jazz it up with brooches and/or snazzy buttons (like this one).

Take Shannon for example. I love how Shannon’s look is classic yet bold at the same time. You can see her personality shine through with the bright orange blazer, yet since it’s such a classic piece it reads as a nice statement and not “too” trendy.

style in your 40s, 50s, and 60s
via Shannon @oysterstopearls

You all know that a white button-down belongs in every woman’s wardrobe (read about the staples you need here), and it looks perfect paired with these light washed straight leg jeans. Frayed hems add a touch of playfulness and youthfulness to the look, without going “all-out” on jeans full of rips from the crotch to ankle (avoid pairs like this), which personally, I don’t think is all that great- no matter your age!

Be thoughtful with your accessories

Less can be more but that doesn’t mean you have to leave the house with an empty and boring look. Accessories really are key and this is great news because you don’t have to be a certain height, weight, or age to rock them. I’ve talked with many older women who are unhappy with their weight and want to look good but don’t want to buy any new clothes. Does that sound like a dilemma you’re having? Here’s what I say…throw a scarf on, girl! Meaning, accessories are for everyone and it doesn’t take much to add style to your look.

Take Renia as an example. I love her simple yet thoughtful approach to accessorizing her look. Classic black sunglasses with a touch of gold? Perfect. A simple pearl necklace? Yes. A timeless leather watch? Love it. And of course, you know how I feel about Chanel…. *heart eyes*

These accessories *need* to be in your wardrobe. Add them to almost anything to enhance your look. Related: 8 Classy Accessories to Improve Your Outfit

style in your 40s, 50s, and 60s
via Renia Jaz @venswifestyle
newsletter sign up free printables

Pair dressy with casual

One fabulous way to be stylish and wear the clothes instead of the clothes wearing you is to mix different clothing styles. Such as feminine + masculine or in this case, polished + casual. Alexandra pairs a tailored blazer and simple yet classic jewelry with casual jeans and sneakers. Not only is this a great outfit juxtaposition but it’s versatile too, allowing you to wear your more polished pieces “on the streets” and not just for work events.

Do you have some fancy work chinos? Pair them with a graphic tee and sneakers!

style in your 40s
via Alexandra @alexajanke

Embrace playful silhouettes

Do you think flirty dresses are reserved just for the “younger” crowd? Think again. In fact, there’s a level of confidence and style that exudes from an older woman that’s confident enough to rock a summery flock. Dressing for your age isn’t synonymous with looking dowdy, as long as you keep some key style tips in mind.

A knee-length or midi length would be best to look age-appropriate. If the length is on the shorter side, long, billowy sleeves balance out the proportions as well as add a playful touch. Have fun with fashion and embrace ruffles, colors, and interesting details. Fashion is not a “young person’s game”, ladies! I like this dress and this dress for age-appropriate options.

Consider pairing your flirty dress with flats, sandals, or even sneakers. If you prefer to wear heels, air on the side of less height if you already have a shorter dress.

Don’t want to show off your bare legs? Try to steer clear from nude tights at least. Instead, look for a flirty dress in a midi length and add some height and appeal with a taller shoe- such as a wedge. When your dress is longer you can get away with a higher heel. I like this dress, this dress, and this dress.

style in your 40s, 50s, and 60s

Dabble in unconventional materials + pay attention to details

I call this unconventional because I would assume that most older women think they couldn’t possibly pull off something like leather pants. So wrong! Maybe you don’t go skin-tight, but you can totally rock something.

Renia shows us a classy way to wear leather/shiny pants in a sophisticated culotte style. Her layering adds style as layering always does and a pop of chartreuse is unique and unexpected. The devil is in the details and that’s something to pay attention to whether you’re 25 or 65. Though mixing metals can be done, I love how Renia keeps the touches of gold throughout her outfit with her sunglasses, chain collar, and shoes. The chain from her collar matches the chain on her shoes and that’s just icing on the cake.

She shows us that you can most definitely rock heels past 40+. I hope you’re getting a theme throughout this post so far- part of having style in your 40s and beyond is about making small adjustments to what you’ve always worn. Perhaps you don’t wear stilettos but you can wear a sophisticated slingback heel and still get the same effect!

style in your 40s, 50s, and 60s
via Renia Jaz @venswifestyle

Know that classic never fails

If you’re a faithful reader of this blog then you know that classic fashion is something I talk about extensively here so I apologize for going over it again (but not really hehe).

One foolproof, guaranteed way to dress like an amazing, stylish, and timeless woman at 40, 50, or 60+? Go classic.

This means neutral colors, timeless prints, and classic pieces. Everything that Alexandra is wearing below is in style now, was in style in the past, and will be in style in the future. You can never go wrong with soft, creamy shades as well as a plaid scarf. Riding boots date way back to the 10th century and though they’ve evolved over time, that’s a style you can definitely count on.

Want to know other styles you can count on? Check out the posts below:
40+ Classic Outfits for Any Age
How to Have a Modern-Day Grace Kelly Style
Capsule Outfits That Build a Timeless Wardrobe

style in your 40s
via Alexandra @alexajanke

Take chances

It might seem a little opposite to wrap up with this point after just talking about being classic, but it’s important to know that you can do both. Yes, it’s totally okay to know what you like and feel comfortable in that, but it doesn’t mean you have to stay like that for the next 30 years. Take fashion chances. Try something risky! Try something new.

Wear the glam earrings during the day. Belt your puffer coat. Borrow from the boys and wear a men’s tie or suspenders (I’ve tried that!). Paint your nails black. Get some knockout boots or a statement skirt.

The classics will always be there for you. Start small and work your way up or just add one unique piece to a classic look. Related: How to Mix Staple and Statement Pieces

Developing your personal style and the thing that makes you you, is what ultimately sets you apart as having style in your 40s, 50s, and beyond!

style in your 40s, 50s, and 60s
via Renia Jaz @venswifestyle

Did you like these fashion tips on how to have style in your 40s and beyond?
Then I just know you’re going to like these next posts:

What my 58-Year-Old Mom Has to Say About Fashion
How to Dress Like a French Woman Over 50
Fashion Over 50 | Aging With Grace & Accepting the Size You Are Now

my chic obsession signature
look stylish past 40


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.