Stop Worrying About Dressing Appropriately For Your Age

What if I told you that we’ve got this whole conversation about age-appropriate dressing wrong?

Dozens of times a day, I am asked about how to dress age-appropriate. 

It’s the first sentence of every email I receive from readers looking for advice, “Hi, I’m 61, 32, 54 … can I wear …?”

So today, I want to share my rather radical approach to age-appropriate dressing to release you from the concept that your age is somehow restricting your choices. 

What if, instead of looking at our age as a limitation, we view it as an opportunity.

Crazy, right? 

I started my career shopping for and dressing women when I was a 22-year-old baby. Today, I’m 40, a mother of three with 20 years of experience, both personal and professional, under my belt. 

In the past two decades, I learned so much about the challenges real women face while aging. First-hand, I know that it isn’t easy maintaining our sense of self and style in a world that wants to limit us after we turn a certain age. 

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

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” wear, it’s time to embrace the world of opportunity that awaits us with each passing year. 

This site focuses on timeless, classic, ageless style.

Classic style is inherently ageless. You may have to replace a piece I recommend here or there 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 the idea of 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.

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

Age, as you’ll see, is the last piece to consider. 

How to Dress Age Appropriately

My first and only tip is to Stop Worrying About Dressing Appropriately For Your Age.

How to Dress Age Appropriately

A New Way to Think About Age Appropriate Dress

Body type is the most important factor to consider. Wear clothes that work best for the body you have right now. Take some time to learn about the most flattering shapes and silhouettes for you. It makes all the difference in the world.

Let’s use an example. Say you are 48 years old and look incredible in a pair of faux leather leggings. You already know they work for your body type. Now what?

Consider your lifestyle or the specific event you are dressing for. Can you wear them to church, temple, or any religious service you attend? Probably not.

But a girls’ weekend in Vegas or a date night out in the city? You bet.  

Now let’s make sure they look elevated. Buy the best quality you can afford, spend a little more, or find a better pair at a discount. At 22, you’d probably grab a cheap pair at Forever 21 today; you’ll buy them at Nordstrom. 

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

At 22, you’re wearing a tank top; at 48, pair them with something more sophisticated, like a cashmere sweater or tailored blazer and heels you can walk in. By pairing them with more “grown-up” pieces, you’re grounding the look to match where you are in life. 

My Best Tips to Timeless, Ageless Style

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

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

The challenge with patterns is that there are so many in retail that looks cheap and flimsy and does nothing to elevate your style. Use them with a light hand. A few dresses in the summer are fabulous. A fun pair of pants? Sure!

But as a layer or a top, they need to make sense and bring value to the outfit. And you need to LOVE It. 

Incorporating texture, instead, is a more sophisticated way to elevate your look.

Be judicious with pattern and bring interest to your outfits with textures and layered accessories. 

Invest in Your Accessories

Nothing elevates a look more than your bag and shoes. Investment is different for every person. Today, at my age, I would rather have a few better quality shoes than a closet full of heels from the DSW clearance section – which use to be my jam.

Maybe Stuart Weitzman and Jimmy Choo are your kinds of splurges, or perhaps it’s Nine West and Sam Edelman; in any case, always look to evolve the quality of your pieces.

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

If you were my best friend and found out you were shopping in the juniors department, I would say this: You’re too old. I am too old. Anyone over the age of 25 is too old. 

Is that offensive? I don’t think so. 

Here are my go-to stores and brands for our over 35, 40, 50+ clients; many includes plus, petite, and tall options in their inventory. 

“Age Appropriate” Department Stores 

Nordstrom has always been my favorite, but I’ve found them more challenging to shop over the last few years. I like some of their private label brands like Classique and Nordstrom Collection; if you like St. John, they have a decent selection that isn’t as overwhelming as shopping in their stores. 

Their shoe selection is still the best out there, as is the range of undergarments they offer. I’m less than thrilled with their in-store accessories, and their plus and petite section leave a lot to be desired.  

Service is not what it use to be, but it’s still better than anything else out there.

Lord and Taylor – their customer service is abysmal, but they have an excellent dress selection for work or special occasions in various sizes and price points.

Neiman Marcus – actually has some reasonable prices and better quality. I love their private label sweaters, especially the cashmere. They also have a great shoe selection and better separates.

Brands (that aren’t cut for kids):

Anne Klein

Ann Taylor



Banana Republic

Clavin Klein

Eileen Fisher

Lafayette 148

MICHAEL Michael Kors




Elie Tahari

T. Tahari

J. Crew

J. Crew Factory

Enjoy Getting Dressed!

Remember when fashion magazines would do Style at Every Age issues and spreads? I read them religiously. Even when I was in my late teens and twenties, I always loved what the 40-year-olds were wearing. 

Looking back, I think it was because the women, usually a celebrity, always seemed so poised. Like she wasn’t figuring things out anymore. The experimental phase of life was over. 

Her pieces were well made, they fit beautifully, and the woman carried herself with quiet confidence. 

That’s what I think we need to celebrate. The confidence, the knowing, the respect we have for ourselves, the not caring so much about what others think. 

And how lucky are we to be living in a time when we are finally celebrating women getting better with age? 

So when dressing your “age,” don’t focus on what you can’t do or what you have been told to avoid. 

Instead, celebrate where you are in life by investing in better quality, focus on fit, and include sophisticated elements that elevate your look.

Have fun and wear what makes you feel confident. Do that, and you’ll create a timeless, always appropriate personal style no matter your age.

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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If you enjoy our content and would like to help us grow, please  follow on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

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Stop Worrying About Dressing Appropriately For Your Age

28 thoughts on “Stop Worrying About Dressing Appropriately For Your Age”

  1. 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?

    • 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!

    • 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!


      • Hey Sue, I should probably note that not all pattern is the same. You probably know I wear a lot of Diane Von Furstenberg. Her patterns are unique and bold but still sophisticated. If you have a few blouses from Ann Taylor I’m sure they are lovely and add interest to your look.

        What I mean is more arbitrary pattern, meaning it’s not thoughtfully incorporated into a look, rather just “thrown on” with a pair of pants. Think those old Jones New York tanks and tops, or anything from Chico’s. Those things everyone can get rid of 😉

  2. 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?

  3. 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!

  4. 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!!

  5. 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

  6. 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.

  7. 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!

  8. 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,

  9. 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

    • 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.

  10. 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??)

  11. 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

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

  13. 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!


  14. 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?”

  15. 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.

    • 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?

  16. 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.

  17. 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.

  18. 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!

  19. 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.


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