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Stop Dressing Appropriately For Your Age

Dozens of times a week, I am asked about age-appropriate dressing. 

“Hi, I’m 61, 32, 54 … can I wear …?” or “Now that I’m 50, I don’t know what I can wear.”

So today, I want to dive into this big, nuanced topic, starting with the fact that you can wear WHATEVER YOU WANT.

I have never once heard my husband ask, “Am I too old for this?”

And would beat that no man on Earth has ever uttered those words.

Certainly, with age inevitably comes change.

But that’s very different than thinking because you are a certain age you now have to dress a certain way. 

At 44, I wouldn’t be caught dead in what I was wearing at 22 because my body and style have changed, and, thankfully, I can spend a little more now than I could then.

But I would never say I couldn’t wear something simply because I’m over 40.

Happily, we live in a time when the conversation has shifted from “anti-aging” to health and vitality.

We want to feel youthful rather than look young.

So what if, instead of viewing our age as a limitation, we consider it an opportunity? Because if you keep thinking you need to follow “rules” when it comes to getting dressed, you’re just making it harder on yourself.

Stop Worrying About How to Dress Age Appropriate

Stop Worrying About How to Dress Age Appropriate

I know firsthand what comes with aging.

I’m 44, a mother of three, and I have a lot of life under my belt.

Maintaining my sense of self and style in the modern world, which is still so rooted in misogyny, is challenging.

Add to that our ever-changing bodies and increased personal responsibilities, and it’s easy to see how many of us, myself included, can get into a rut or feel like we have lost our way.

Related: How to Stop Feeling Frumpy

It’s frustrating because many options in stores seem like they’re for kids at the club or 80-year-olds in a home.

So before I get into the nitty-gritty, let me say this: the one thing I know for sure is that we’ve got this whole age-appropriate conversation wrong. 

Aging should be a celebration, so instead of thinking of all the things you “shouldn’t” or “can’t” wear, it’s time to embrace the world of opportunity that awaits us with each passing year. 

And the good news is that classic style is inherently ageless. 

You may have to replace a piece I recommend with something that works within your budget or with your body type, but the style tips and theories offered here are all timeless. 

I’ve never liked telling women what they should and should not wear. 

Instead, I hope you see this site as a guide to achieving a modern, classic style with a bit of a twist, regardless of the year you were born.

My job is to provide options to our community, which means that, based on your style and needs, not all of them will speak to you. Still, all the recommendations are under the umbrella of classic, modern style.

Over the years, I’ve created a hierarchy or checklist for clients and readers to go through when they wonder about mental appropriateness.

As you’ll see, age is the last piece to consider; even then, it’s not what you might think.

How to Dress for Your Age

Do you want to know how to dress “for your age”?

Stop thinking about it.

Instead, filter your choices through a few checkpoints and you’ll always look and feel great.

A New Way to Think About Age Appropriate Dress

Age Appropriate outfit

Body Type

The truth for most of us is that our bodies change with age, so focus on wearing clothes that work best for the body you have right now and make you feel confident.

Take some time to learn about the most flattering shapes and silhouettes for you.

It makes all the difference in the world.

Be sure to read our How to Dress Your Body Type Guide Here. 


Understanding your current lifestyle is surprisingly critical in making good purchasing decisions.

I work with many women who love the idea of an outfit or specific piece but have no place to wear it.

So, ask yourself, where am I going in this?

And can you wear it a few different ways or to a few events so you get your money’s worth?

Otherwise, it’s not an appropriate purchase.

Quality and Fit

As we age, many of us begin to appreciate quality and look for a more sophisticated style.

Buy the best quality you can afford, spend a little more, or find a higher quality garment at a discount. 

Consider fit and custom tailoring, like a hem, or having your waist taken in – spend on the small details, things we we never thought of when we were younger.

At 22, you grabbed something disposable off the rack at a discount store; today, you’ll pay a little more at a better department or speciality store so you get a better product with a longer lifespan.

Finally, by the time we turn 40 we have a clear idea of who we are. Maybe your personal style isn’t fully formed yet, but you know what you like and dislike.

Is there a look you aspire to create?

A way you want to live?

These are the decades to do it in.

There is no such thing as age-appropriate

Our lifestyles, bodies, and personal style profiles are wildly different from when we were younger.

And that’s ok!

In my twenties I ran around in low slung jeans. I don’t do that now, not because I’m 44 but because I three C-Sections. If I still had rock hard abs, maybe I would still show them off.

Our tastes evolve with time for most of us, and we don’t like the same things we did in our younger years.

We’re also a whole lot smarter.

Remember the days of going out for the night in the cold, wearing sky high heels and no coat?

Can you imagine doing that now? We didn’t always make great choices … at least I didn’t.

With age comes wisdom, and now I know it’s not worth traumatizing my feet and getting frostbite.

And guess what?

Young women now have more sense than we did because they have no problem wearing their sneakers with their party dresses.

My Best Tips to Timeless, Ageless Style

How to Dress Appropriately For Your Age - The Well Dressed Life

You can see that age is simply the catalyst for changes that affect how we want to look and dress.

Quality over Quantity

Get comfortable with the idea of investing in yourself. 

Buy the best quality you can afford. 

Start to think strategically about the items in your closet so you get more wear out of fewer, higher-quality pieces. 

Be Cautious with Patterns

I’m not telling you never to wear a pattern. I love some bold patterns, especially in the warmer weather. 

The challenge with patterns is that so many in retail look cheap and flimsy and do nothing to elevate your style. 

Use them with a light hand; remember, you must LOVE them.

Don’t wear prints and patterns to “spice up” your outfit.

Instead, incorporating texture is a more sophisticated way to elevate your look.

Invest in Your Accessories

Nothing elevates a look more than your bag and shoes. 

Investment is different for every person. 

Today, I’m at a place in life where I would rather have a few better quality shoes than a closet full of heels from the DSW clearance section – which used to be my jam in my youth. 

When it comes to bags, look for simple, clean designs. 

Avoid logos, studs, patchwork, or anything that dangles, like charms and chains. 

You don’t want your bag to fight with your outfit.

And wear your better jewelry every day – what are you waiting for? 

Shop in the Right Stores

The only time our actual age comes into play is when it comes to where to shop because stores and brands target specific, age-driven demographics.

So, if you were my best friend and I found out you were shopping in the junior’s department, I would, without hesitation, tell you you are too old to be there.

The clothes in junior departments and youth-focused stores are cut for the bodies of teens and early twenty-somethings.

Plus, they are cheaply made and have minimal size ranges.

But, these days, the real challenge is finding clothes for grown women that hit the sweet spot of being sophisticated, fresh, modern, youthful, practical, and stylish.

The good news is that we provide daily inspiration, recommendations, and advice to keep you looking as ageless and timeless as possible.

Stop Dressing Appropriately For Your Age

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Haydee Betancourt

Friday 25th of October 2019

Hello, I stop by accident on your website and to bee honest, I just love what I have read so far. I read you're suggested list of the essential pieces you need to have in the closet and going to look for it. One thing, from the list can you show some samples of the Clothes ?.Also the underwear and bra (quantity, quality brand etc... I like your advice, Thank you

Megan Kristel

Saturday 26th of October 2019

Hi there, thanks! Examples of the clothes on the essential list are within all of our posts and vary depending on the person, their budget, style and body type.


Wednesday 16th of October 2019

Megan....I am finally beginning to understand what I have been missing! I have been "lost" in the 80's forever... however I have been uncomfortable with my go-to jeans and tee shirts..I have loved learning what I like with you. Thank you so much, Valerie


Wednesday 16th of October 2019

Hi Megan! I love this post, and can relate as I just turned the page into my 50s... My go-to store is Banana Republic and find that their classic and diverse options in blazers and pants (Sloan cut, etc) are perfect for work and other social events! So much so that I have invested in 2 pairs of the Black Sloan cut pants because I wear these black pants so often - and I never have to worry when one pair is at the dry cleaners. Speaking of which, BR is now offering many pants that are now Machine Washable : ) which saves on the bank account! Another reference for Ann Taylor...this past summer I was struggling with finding shorts that were appropriate for my age - it was finally time to retire the Lilly Pulitzer shorts - LOL (and the state of my legs - although I am doing yoga and exercizing - we all know that the thigh areas change with age...). Anyhow - they had the BEST pair of shorts - high-waisted, not too short and with a fabric belt in a quality fabric! I tried them on in Black and ended up buying them in 2 different colors! Thank you so much for your blog - I have purchased many items based on your suggestions and always look forward to the next one!

Johnsie Krause

Tuesday 15th of October 2019

What do you think of Chico's brand

Mrs RW

Tuesday 15th of October 2019

Thanks so much for this. As someone also turning 40 in a couple of months, I've really been looking for ways to elevate my style. I look pretty young for my age so can still get away with some teeny bopper stuff, but I'm ready to be seen more in line with my true stage in life.

Gail Green

Tuesday 15th of October 2019

Great article. I want to thank you particularly for the comments about Nordstrom’s. I’m a retired healthcare executive and bought a lot of my professional attire there. I now live in a city with 2 Nordy’s and find the stores have changed (negatively) with a ton of ‘open’ floor space, poor to lacking inventory etc.. I thought I had lost my mind but you saved me! LOL Thanks again for this article and for your blog. Best wishes. St Louis


Tuesday 17th of April 2018

I love this post! Like the other comments I would love professional looking summer items. Love your blog!


Monday 16th of April 2018

Thank you for this, you NAILED it! Your advice is specific, logical, and most important, actionable. Body type, lifestyle, budget, age -- I will write this on a post it and refer to it when I shop :) Love your blog so much, keep your awesome tips coming!!

Megan Kristel

Monday 16th of April 2018

Thanks Kristin! What a nice comment to read on a Monday morning! :)


Thursday 12th of April 2018

Thank you Megan. Great tips... Like C, tips on summer casual dressing would be great. Especially comfy sandals/shoes that don't make my feet hot or look really frumpy. I'm starting to think I'll see a unicorn before I find a cute comfy sandal!


Thursday 12th of April 2018

I find it much harder to dress in summer for some reason, perhaps because in winter I can layer more and create interest. In summer, I feel less put together and that I'm dressing too young. And it's super hot where I live so I'm mostly in sleeveless tops or dresses. Any tips on summer-casual specifically for the 35+ crowd?


Thursday 12th of April 2018

Hi Meg, I'm looking forward to your upcoming posts on more on age-appropriate outfits. I'd love to see some suggested pieces for women in their 40s who are young at heart (like me). I'm newly single and I go out places where women are much younger than me (clubs, lounges, etc). I don't want to look like a Talbot's model yet I don't want to look like I'm trying too hard. And every 40-something woman seems to be stuck in the skinny jeans-blazer-heels look for going out. Any suggestions? Elyse

Sue C.

Thursday 12th of April 2018

Hi Meg!

I love your blog so darn much, buuuuut... I have to disagree with you about patterns. I have several wonderful pieces from Ann Taylor (a store you listed above as a go-to!) that are FABULOUS! They're tailored well and look timeless yet modern. I mean, c'mon... it's Ann Taylor!

BTW... if you haven't seen or heard of them, check out Boden Clothing. I came to know Boden when I was working in financials in NYC. My UK office counterpart would come to visit and always looked sharp yet comfortable and cute, and she was in her 20's at the time and I in my mid 30's. Even though I can only afford it when it's on-sale, I absolutely LOVE their things to this day (I'm now 52 - that's 25 backwards!!) :-) It's kind of like the Europe version of Ann Taylor with a little Loft adventure, and J-Crew mixed in for contemporary and modern taste. Thankfully they distribute here in the U.S. too!


Megan Kristel

Thursday 12th of April 2018

Thanks Elyse! It's funny, I was just at dinner with Lauren last weekend, and there was a parade of over 40 women at the bar, all in some combination of blazers, skinnys and heels. I post on some other options is on the calendar. Stay tuned!

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