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

BOSS

Boden

Banana Republic

Clavin Klein

Eileen Fisher

Lafayette 148

MICHAEL Michael Kors

Talbots

Tuckernuck

Everlane

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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Wear to Work: 5 Black Dresses for the Office that Aren’t Boring

Wear to Work Outfits - 5 Black Dresses that aren't boring

Ten years ago I bought a dress off the clearance rack at Banana Republic. I remember it was on sale for about $40.  It was sleeveless, with a slightly scooped boat neckline, and made from a double-knit cotton with a nice amount of stretch. The waist had a seam detail with deep knife pleats along the top, and, best of all, it had pockets.

It was one of those magical dresses that fit me no matter my size or the state of my body. It took me to cocktail parties, business meetings and hundreds of client appointments.

I only recently retired it and sent it off in my Thred Up bag.  Unbelievably, after all those years and all those wears,  I still received a few dollars for it at resale.

Talk about price-per-wear! The dress owed me nothing.

That’s the beauty of a little black dress, it has some major staying power, even with some extra style details. In fact, that’s what I think gave that simple, inexpensive dress such longevity: it’s subtle yet significant details.

I’d love to replace it with something equally timeless and interesting. So I started looking and found several beautiful options, many also on sale at a can’t beat price.

Today, I rounded up five the best black dresses that have the same timeless quality as my magic dress did.

Note: Because of the time of year, sizing on many of these are limited so act quickly.

Wear to Work Outfits - 5 Black Dresses that aren't boringFrom Left to Right: Liz Claiborne, $50  |  London Times, $55  |   Donna Karan, $69  |   J. McLaughlin, $215  |  Ann Taylor, $55

Liz Claiborne, $50: There is a lot to like about this jersey stretch number, from the work appropriate length skirt to the long sleeve, but I like the asymmetrical neckline best. You can wear it to work with an oversized earring and basic pump or dress it up for a business dinner. (Also available in a bold blue, in sizes 4 – 18).

Plus size? This is a similar option also in black and blue. 

London Times, $55: Another long sleeve option, with a longer hem – you can always have the hem shorten if it hits you too low on your leg. Ideally, for this cut, you want the hem to hit right at or slightly above your knee.

Style Tip:  The v neck line is universally flattering, and the ruched detail at the center of the waist will bring the eye in, helping to show off your shape. Remember, everyone, regardless of size, has a shape, that you want to highlight not hide.

For a plus size alternative, this Tahari is pretty much perfection.

Donna Karan, $69: This dress is quintessential Donna Karen, for under $70.  It’s simple, chic and a little sexy, in a way that allows you to look professional too. The side tie detail does the same thing for your shape as front ruching, this time it’s just pulling the eye to the side, but the effect is similar. Because of that side ruching, skip any kind of necklace and opt for an earring or statement shoe.

J. McLaughlin, $215: The most expensive dress on the list is also the most basic. The front seams is hard to see in photos, but gives a modern vibe in person. And the keyhole back detail looks sweet with upswept hair.  Plus, there are pockets … I mean, who doesn’t love a dress with pockets?

Ann Taylor, $55: Lastly, this basic black wrap, with a high front hem, looks a lot like a DVF for a fraction of the price. I would skip wearing it to work, but I would wear it to work-centric functions, like a holiday party, or cocktail party at an industry event.  Watch how high the front hits you. I’m 5’10, and this would be too short in the front, but if you are 5’7 or less, it will work well.

This City Chic dress at Nordstrom has a similar feel at starts at size 14 to 24.

Shop this Post

White Jeans for Every Age

For the Ages: White Jeans - The well Dressed Life

Continuing our conversation about age-appropriate dress, we’re talking about white jeans. This time of year, nothing brightness up a look like a crisp, well-tailored pair of white jeans. Interestingly, we’ve received many requests for not only recommendations on the best pair, but questions about what age is too old to wear them.

So let’s dive into the later. You’re never “too old” to wear anything. If you want to rock a tube top and booty shorts, and you have the body and a place to wear that, be my guest. But, chances are, you’re style has evolved since those days, and you’re more interested in looking modern and stylish. The most important factors to consider when “dressing your age” is your body type, and then your lifestyle, and then the occasion.

Age is never a real factor.

But with age comes changes to our body and lifestyle, and hopefully, a little more budget.

For the Ages: White JeansJeans, $178

When it comes to white jeans, I spend.  I find the quality so much better.  You’ll get coverage, proper pocket placement, fabric and overall fit. All of which are super important because white jeans can look bad real fast. In my early 20’s, when I didn’t have hips and a full bottom, any old $20 pair of jeans from H&M worked.  I didn’t even have to try them on in the store.  These days, I need a little more to accommodate my grown woman body.

Generally, a straight leg will give you the most tailored look and go with any style top.  My favorite style is DL1961’s Mara jean in “milk.” They give you a long slim leg without clinging to your body, and a higher waist for some added support and better fit.  They’re not cheap, but you just need one pair, and with proper care, will last season after season.  Alternatively, these NYDJ are slightly slimmer through the thigh, but wider in the calf and available in missy and plus.

If you’re looking for something a little less expensive, you can try these under $100 ankle length jeans from Talbots in a wide range of sizes, or  these classic Levi’s for under $60 .

Do you have to only wear straight leg?  No, but they are the most universally flattering.  I still wear skinnies, and also have a pair of skinny distressed .

 

 

 

Classic White Button Down for Every Age

For the Ages: Classic White Button Down - The Well Dressed Life

Today we are launching our age-appropriate series, “For the Ages.” I’ve thought long and hard about how to organize and break these posts down. I decided against offering suggested based on a specific age. What one person can wear at 45 will look different than someone else. Instead, I want you to focus on fitting your body type.

I’m considering using myself as a model in the future since writing a post about age-appropriate classics feels a tad disingenuous when featuring a 19-year-old catalog model.  However, the only person who can take my picture without requiring payment is my husband, so we’ll see how that goes. I’ll need wine, maybe a valium, and marriage counseling. Until then, we’ll start with an emphasis on wardrobe basics, kicking off with the classic white button down.

For the Ages: Classic White Button Down

Brooks Brothers Non-Iron Ruffle Pinpoint Oxford Dress Shirt, Missy and Petite: $118.00

The classic white button down made famously approachable by the epitome of style herself, Carolina Herrara, should be a staple in your closet. You can wear it in a dozen different ageless ways to create a truly timeless look. My favorite combination is tucking  it (full or half)  into your favorite dark jeans (in whatever fit works best for you) and dark tan accessories, like a woven belt and block heeled sandals.

You can keep it classic with slim black pants and black mules for a more relaxed office ready outfit.  Or use it as a layer under a long cardigan, or denim jacket. For the weekend, create contrast by pairing it with a sporty pieces, like these olive skinny jeans, or these preppy printed pants. 

Scroll below for some of my favorite options for any size and age, and let me know in the comments what pieces you would like us to feature in upcoming posts.