How to Dress Appropriately For Your Age

I have long hesitated to dive into the topic of “age appropriate” dress for many reasons. At first, I simply didn’t feel qualified to address the question. I started shopping for and dressing clients when I was 27 and for years I did everything possible to appear older (imagine that). My inferiority complex was fierce.  I looked and felt like a kid.

Today, I don’t like the idea of telling women what they should and should not wear based solely on age. In fact, I hate the idea of telling women what to wear at all. Instead, I hope you see this site as a breakdown of how to achieve modern, classic style with a bit of a twist.

“Age Appropriate” is an almost impossible topic to unpack without unintentionally offending someone. With that in mind I want to make a few things clear before we dive into a discussion:

– Our site focuses on timeless, classic style which in and of itself is inherently ageless. You might 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 are all the same. Promise. I think it’s more helpful for me to talk at a macro level than get into the micro because we have thousands of readers and everyone is so different.

– There is no more sure fire sign that something is right for you then when it creates a visceral reaction in your gut.  If you feel truly amazing in something, wear it and don’t worry about “rules”.

– Body type is perhaps the most important “appropriate” factor to consider, then lifestyle or the event your attending, then maybe budget, then age. I’ve worked with tons of women over a certain age, and no one body type was ever the same. I’m thinking of one client in particular who could pair H&M with DVF better than any 25 year old. That said, being over 50 isn’t a life sentence to Eileen Fisher – unless you love Eileen Fisher and if so wear it, it’s just a very specific style. You know what I mean.

With all this in mind, I have a few tried and true guidelines when it comes to (gulp) dressing your age.

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

Quality over Quantity

My soon to be sister-in-law is 28. When she wears a $30 dress, she looks like a goddess.  If I wore the same dress I would look like a tragic before picture in a makeover contest.  But I’m ten years older than she.  I also use to be able to wear a tube top without a bra, but then I had babies.  Life happens and bodies change.  I feel stronger and healthier now than I ever had, but I know my limits.
As we age, investing in better quality pieces creates a sophisticated look.

Ditch the Patterns

I take a lot of heat for this, but I am unapologetic about my thoughts on patterns. Do you have inexpensive, v-neck, 3/4 sleeve tops in your closet covered in a random pattern? Keep them if you are going for artsy and eccentric. Otherwise, most pattern, especially done in a stretch fabric, is not going to get you the classic, timeless look you are trying to create.

Ditch the pattern and bring interest to your outfits with textures and layered accessories. Texture adds depth and visual interest in, you guessed it, a more sophisticated way.

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 or Jimmy Choo is a splurge, perhaps it’s Nine West, in either case always look to evolve the quality of your pieces.

When it comes to bags, look for simple, clean designs. Avoid logos, chains, studs, patches or anything that dangles.  You don’t want your bag to fight with your outfit.

Shop in the Right Stores

I know what you’re thinking, “all this sounds great, Meg, but where am I shopping?”

Retail, especially in its current state is incredibly frustrating.  Most stores cater to the youth culture while ignoring grown, professional women with an actual budget.  I know how hard it is because I use to shop for a living. Here are my go-to stores and brands for our over 35, 40, 50+ clients:


Nordstrom – has always been my favorite but over the last few years I’ve found them more difficult to shop.  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.  I’m less than thrilled with their in-store accessories and their plus section could use a little love.  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 a nice dress selection for work or special occasions in a range of sizes and price points.

Neiman Marcus – so pricey, often pricey for no reason, but they have a good shoe selection and better separates.  I also love their private label sweaters, especially the cashmere.

Brands I turn to that aren’t cut for kids:

Anne Klien
Ann Taylor
Clavin Klein
Eileen Fisher
Lafayette 148
MICHAEL Michael Kors
Elie Tahari
T Tahari
J Crew
J Crew Factory

I use a site called to look for a specific item across all of retail.  It’s incredibly helpful because you can sort and filter by size, store and brand for a narrow focused result.

Because this topic has been so popular lately, we are working on a weekly or bi-weekly series where we break down certain wardrobe classics and offer options based on age.  I’m still working out the details, but we’ll have it up in a few weeks!


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.

  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?

    1. 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!

    2. 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!


      1. 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!!

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