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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. 

Lifestyle

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
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 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.

MEET THE AUTHOR

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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Debbie Licciardi

Monday 14th of August 2023

Hi Megan,

Where did you buy the cream dress you are wearing in the picture for this article Stop Dressing Appropriately for Your Age? It is very pretty. You probably shared it with suggestions on what to buy in an early email, but I cannot find it.

Thank you, Debbie Licciardi

Teresa

Tuesday 8th of August 2023

Thank you for this article on dressing 'age appropriate.' I have felt for years like my choices were looking like a teen or a great grandmother. I'm in my 60s and trying to dress better. Somewhere along the way I lost my sense of style.

I'd love to see an article on incorporating fine jewelry. I see a lot of fashion jewelry and statement pieces. I don't really own any of either. I have a few pieces of fine jewelry I have accumulated through the years, but feel they look so plain.

Jen M

Tuesday 8th of August 2023

Great article! I am 53 and have spent time trying to discover my personal style and money to invest in more classics pieces. One thing you said above struck a chord as I have neglected my accessories, specifically shoes and handbags. That is something I need to focus on next in this journey. Thank you for this and all the articles you post!

kitykat

Tuesday 8th of August 2023

Hmm, yes, 'age-appropriate'. I do enjoy your blog, even though, at almost 80, I'm WELL past your target. However, finding clothes that are suitable for non-working mature women is not that easy! Like the other commenter said, Nordstrom has changed. Empty like an art gallery. Even the upper mid-price at Dillard's and Macy's have poor choices. Ugly, garish prints, and oh-my-gosh everything has ruffles! Thin fabrics and poorly fitting. I'm a 10-12, depending on cut or price point, so not overweight or frumpy. Just where do I and my elderly sisters go?

Tracy Gray

Wednesday 12th of January 2022

Love this!! I have so often felt unsure of what I liked and wanted to wear because at 62 I don’t want to look like I’m dressing younger than I am and will look ridiculous. It sometimes just brings me down but I have read and reread this and it really helped. Thank you so very much!!!

Andrea Johnston

Tuesday 11th of January 2022

Meg, Thank you! thank you! thank you! This is what I have been thinking these last couple of years . I am definitely leaning into "quality over quantity", That is connecting the dots for me!

Mary

Tuesday 11th of January 2022

Thank you for this article, I am going to keep it for the next time I feel insecure about my choices. At 71 I have found it increasingly difficult to find “age appropriate” clothes and now realize that maybe my choices haven’t been so very off point.

Averil

Tuesday 11th of January 2022

Hi Meg:

Thank you for emphasizing the need to purchase better quality. I admit I often buy items because they are inexpensive, or on sale for a great price. I am trying hard to purchase better quality items. Shopping is difficult because I have a clear idea of what I want, but can’t find it in the stores or even on line. I am seriously considering hiring a fashion consultant, as I am at a loss. I always look forward to your daily posts - lots of good stuff.

Jessica Moran

Tuesday 11th of January 2022

You are awesome! Thank you for this! I feel inspired.

Michele

Tuesday 11th of January 2022

Thank you for a realistic look at this - for many, many, many years I've made my own clothing for the simple reason that anything available in the retail world (at an affordable price) in Canada (where I live) was made for 22-year-olds that worked at the beach! Working in a professional setting most of my career, choices were easy - now that I've been working primarily from home over the past almost two years, I find it difficult to manage a comfortable, pulled-together look. I hope that you'll have some suggestions for those of us that are feeling like fish out of water!

Hollis

Tuesday 11th of January 2022

What a beautifully crafted post! There is so much wisdom and grace in your words-I truly appreciate your site and presence in the blogosphere. You have given me (54 y.o.) incredible tools and resources to feel wonderful in my clothes!

Joanne

Tuesday 11th of January 2022

Hi Meg,

Bravo! Loved this post! Have been following you for about a year now and am never disappointed with your content. Thank you for your encouraging words and attitude! You're an amazing person.

Anne

Tuesday 11th of January 2022

First, I can’t wait for Thursday…I’m so excited! That is the style formula 101 post:) Back to this post, some of us middle aged women still carry body insecurities from our teens. The wardrobe challenge may take many repetitions but the process is extremely helpful. I have had a lot of growth and confidence in building outfits. I may be old but I love to wear the faux leather pants:)

Susan

Tuesday 11th of January 2022

What a lovely article and so encouraging. I read it out to my husband. His comment was - so which person is writing a men's equivalent blog. Retired so not into suits anymore, not ready to be part of the white sneakers brigade and not into MainLine/New England upscale boating styles....what do you suggest please?

Janice Jackson

Sunday 10th of January 2021

I love your blog. I don’t alway get to read it everyday. I try to read is often as I can. For a while I haven’t been able to read is often as I like to. I’ve had some health problems. Thankfully not COVID. I’m trying to catch up. It might take me a while but I will do my best.

Robin Skiles

Sunday 10th of January 2021

Hi, I clicked on the Summer Session but its link is to the Fall Session so I didn't sign up. If you are taking sign ups for Summer, let me know. Very interested!

Lynn

Monday 27th of July 2020

I used to wear a lot of classic tailored pieces, but after many years frankly they are boring. I now experiment more with my style. I am petite and in the past year I have found better and more stylish fitting clothes in the junior department. Probably because they actually have darts and tailored seams which seem to be non-existent in the women's department.

Gail Delsa

Saturday 25th of July 2020

You handle comments beautifully. What wonderful gifts you have. Thank you for sharing.

BETH j

Saturday 25th of July 2020

I am a loyal follower and have bought many of my favorite pieces from your recommendations. I find your blog authentic, practical and supportive. You are incredibly talented! I just loved your response to Sheila A. and wanted to express my encouragement and appreciation for the hard work you clearly do every day! You’re a great role model for women everywhere.

Sheila Al-Ansari

Friday 24th of July 2020

Hello!!!

I'm sorry. I really am. But age appropriate dressing?? Pop a cashmere sweater over your tanktop??? Have I blinked and gone back to 1955?? I'm 64. I wear exactly what I want. I buy anything I like from any store. I have long hair. I wear Doc Martins. Clothes should reflect who you are not who other judgmental people think you should be because you're over "a certain age". Rules? There are no rules. A plus of being older is that you have earned the right to not give two hoots what other people think about you and be free to be you. So....wear mad patterns. ripped jeans, ball gowns, pencil skirts, high heels if you can, ANYTHING GOES.

Candice B

Thursday 28th of October 2021

@Megan Kristel,

I have to agree with her. I'd come here hoping you wouldn't use age as a "thing". You say that out one side but then say consider your age. I agree with the dress to your body type and lifestyle/occasion but those should be your only consideration. Lots of good advice but by even considering age you negated your previous statement.

Megan Kristel

Friday 24th of July 2020

Maybe calm down and reread the post because it's clearly about celebrating age, not letting it limit your choices, and encouraging women to wear whatever they want.

The good news for you is that this site isn't for everyone. I provide tips, tricks, and recommendations for women specifically looking for advice on creating a timeless, classic, modern style. So if you want to run around in a ball gown with Doc Martins, by all means, go for it. That's not what our readers are trying to achieve.

And please think before you come to a site you have never commented on before, barely read a post written to provide encouragement and positivity, and dump your negativity. Seriously, in the current state of the world, how do you even have the energy?

Mrs. Todd

Wednesday 22nd of July 2020

Thank you so much for this! I’ve been editing my closet and adding quite a few of your suggestions for quite a while. Today is the day I set up my closet for “shopping” for outfits from what I already have. Now I’ll add my jewelry to the list. I love the question, “What are you waiting for?”

Tammy Stokan

Wednesday 22nd of July 2020

What a terrific post! I have learned so much from you and while I was always a style conscious dresser, I struggle with shopping and selection but also had a closet of clothes but nothing to wear.

Purging, refining and replacing have been a fun project and for the first time in years, I have a wardrobe that has versatility, style and function covered! As someone who hit that 50th Birthday earlier this year, I appreciate this post. I am not ready to be twins with my Mom and feel that I am a much younger version of 50 than she was at that age.

I will enjoy being the “50 is the new 40” era and live my best version of it with classic and timeless style!

Tammy

Betsy Cornell

Wednesday 22nd of July 2020

I'm going to print this and put it in my fashion journal. Timely and fresh, you're sharing some great tips. Thanks!

Debra Masella

Wednesday 22nd of July 2020

Megan - every single word and thought in this rings completely true to me - love it! You are absolutely right about the bullet points and I could not agree more! Thank you for a thoughful and well said piece

susan klusmann

Wednesday 22nd of July 2020

I am always so happy to see your wisdom pop up in my inbox. Especially this one!! However, I am 73, exercise faithfully, a size 4 often (not with the covid/chocolate 5# so much!), and nothing can cover the fact that my arms cannot go out in public, my feet have bunions and a hammertoe-and I live in Texas where it is hot. Raging hot this summer. Do I just say what the heck and wear sandals anyway? I would love a post featuring classic, cool tops with at least an elbow sleeve and your advice on sandals. Strangely, I have always had a classic style but now look for a bit of an edge, but so often that is shapeless- I am a pear shape, and that is not my best look, but due to gravity, tucking in is getting less flattering as well. I know I am not alone in this quest!! thank you so much- Susan in Texas (did I mention hot??)

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