How Not to Dress Old – 10 Style Mistakes That will Age You

Last Updated on June 6, 2024 by Candi Randolph

It’s probably a fair statement that as women in our 50’s and 60’s we don’t wake up in the morning, gaze into the closet and think, “hmmm…what can I wear today to make me look old and frumpy?”

Of course, we don’t do that, at least not consciously. Because, seriously. Who wants to dress like an old lady? Sometimes, though, we are stuck in patterns and actions that give us a result that we don’t want, without even realizing it. When it comes to understanding how not to dress old, we aren’t doing ourselves any favors.

How Not to Dress Old

So, we may be browsing through our wardrobes, wondering if our choice of attire is a great way to showcase our personality or if it’s silently whispering, “I’m stuck in a style time warp.”

As older women (not OLD, just more mature), we’ve earned our fashion stripes and life experience. We know what works for us and what doesn’t. We’ve defined our comfort zone and, dare I say it, sometimes we’re a little too comfortable.

The good news? These tips will help you avoid those pesky fashion mistakes that are sneakily adding years to your overall look. It’s not about chasing the latest trends, but more about refining a classic look that shows sophistication with a dash of fun.

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How Not to Dress Old

We’ve all had that moment of standing in front of a mirror and thinking, “Did I wear this exact outfit in my younger years?” Or, “Is this still in style?” It happens to the best of us. After all, who hasn’t clung to a particular style or piece of clothing for a tad too long?

Now, don’t get me wrong. There’s no rule that says we need to chase after current trends like we’re playing a game of fashion tag. But, there’s also something to be said about keeping our look fresh and modern, right?

Here’s what tends to happen. We find a style that works for our body type, and we stick to it. And why wouldn’t we? It’s comfortable, it’s familiar, and it saves us the trouble of having to navigate through the ever-changing world of fashion. However, is sticking to the same look for a long time always a good idea? Well, not necessarily.

Think about it this way. Would you keep eating the same meal every day just because it tastes good? Probably not. So why do the same with your style? Remember, variety is the spice of life!

So, how about we take a leap of faith together? Step out of our comfort zones, and embrace the exciting world of fashion that awaits us. Because, we’ve still got it!

Ready for those tips? Here they are.

1 | It’s All in Our Head

For me, it all starts in my pretty little head, not with the clothes I have in my hand. Our perception of ourselves influences every decision we make, including style choices.

  • What am I thinking?
  • How do I see myself as a person?
  • Do I respect myself?
  • Do I think I’m a beautiful person, inside and out?
  • Am I worth taking the time to look my best?
  • Does anyone really care if I throw on any old clothes?

If we look in the mirror and see a middle-aged, heading down the “old lady” path person staring back at us, that can’t help but be reflected in the care we take with our outfit choices.

So if the goal, how not to dress old, is one that you aspire to, remember to start with what’s going on inside your head before dressing the outside.

If you’re not sure how to go about adjusting that perspective and gaining confidence with yourself and your personal style, The Fashion Cure might be just what you’re searching for. It’s a simple email series course, yet full of practical and insightful tools for you as a woman over 50. LEARN MORE

2 | Cranking back the clock

Taking an honest, realistic look at ourselves will help keep us in the present, and that includes our fashion choices.

My outfit choices from 5, 10, or 15 years ago will not be the same today. Why? Well, my body has changed. The weight has shifted to my middle more than in the past, I’m a few pounds heavier, and I definitely think about how much (sagging) skin I am willing to show.

For me that means 3/4 sleeves vs. sleeveless, or, if I wear shorts in public, what length is right for me today?

A woman in her 60’s in a tank top and short shorts is probably not a pretty picture, at least for me. The skin just isn’t as tight, or taut, as it used to be. So why do I want to wear outfits that actually make me look older by shouting to the world, “hey, look at me with my sagging skin and wrinkles!”?

I’ll feel better about myself and actually look younger if I switch out the tank top for a 3/4 sleeve t-shirt and a pair of capris or ankle length jeans instead of the shorts. Age appropriate outfits that are stylish and flattering. Yep, that’s the goal!

3 | Fixed on today’s trends

As a self-proclaimed non-fashionista, I don’t follow the latest fashion trends. I am confident in my personal style and what looks best on me.

Sure, I’ll check out what’s new in the stores, or the popular colors and fabrics, and decide if it’s a good fit for me, literally and style-wise.

If I hop on the latest style train and my motivation is to be “stylish and trendy” without regard to how it actually looks on me as a woman in my 60’s, I could potentially end up looking rather foolish, and old, in a sad kind of way.

Fashion trends are great, don’t get me wrong. Just remember to evaluate first what the impact of that particular choice will have on you, personally. It might be the perfect look for the fashion blogger or the model on the website, but not right for you. If it’s going to make you look older, it’s probably best to let that outfit go.

4 | A bit too bare

I mentioned this earlier, and it deserves its own category because it is that important when your goal is to understand the style mistakes that will age you.

The age-old question: to show more skin or not? It’s a hot summer day, and you’re tempted to reach for that skimpy top or those short shorts. But wait! Before you make this fashion faux pas, let’s chat.

It’s a common misconception that showing more skin will make us look younger. The truth? It can actually date us faster than a reality TV show from the early 2000s. Now, don’t get me wrong. There’s absolutely nothing wrong with flaunting what you’ve got. But when it comes to dressing in our fabulous fifties and beyond, subtlety is key.

You see, trendy clothes are great, as we discussed earlier. They’re fun, they’re fresh, and they keep us connected to the fashion world. But some trends are better left to the younger generation. I mean, do we really want to compete with our daughters or granddaughters in the skin-showing department? Didn’t think so!

So, what’s a mature woman to do? Well, it’s simple. Instead of showing more skin, why not focus on highlighting your best features?

For example, a well-fitted pair of jeans can have a similar effect as a mini skirt – without leaving you feeling overly exposed. Or how about a good bra? More about that below. It’s amazing how the right support can instantly lift not just your bust, but also your confidence!

Remember, friends, less is more. And in the world of fashion, this couldn’t be truer. So, the next time you’re tempted to bare it all in the name of youth, think again. Because style, class, and a dash of mystery never go out of fashion.

Showing more skin will not make you look younger, and in fact can have the opposite result, particularly when the motivation is to try and be more youthful.

It goes back to what is happening in our heads, and how we perceive ourselves. If we choose clothes and style looks that show skin in order for us to feel more youthful, chances are it is going to have the opposite result.

It can be difficult to remain motivated, encouraged, and feel supported when you’re trying to establish a healthy habits and lose weight. Did you know that your smart phone can be a very effective tool for accomplishing your goals to live a healthier life? Learn more about MIGHTY HEALTH, the healthy lifestyle app created for women and men over 50

5 | More sag than support

You know, it really doesn’t matter what you wear if your unmentionables don’t fit properly, particularly the bra.

An instant indicator of an “old lady” look is sagging boobs. It’s that simple, girlfriend.

The bra that worked well for you in the past may not be the best choice for you today. It goes back to our perception of ourselves as well as holding on to past choices without thinking them through.

Many department stores like Macy’s and JC Penney offer bra fittings and/or helpful guides so you can be confident in making the right choice.

When it comes to all-over support, it might be time to consider the world of shapewear. I know…it can be daunting, but I recently reviewed Leonisa shapewear, and as a total newbie to the ‘compression club’ I was quite impressed with their line of products. Check out my review of Leonisa shapewear and see what you think.

6 | Baggy bottom syndrome

Wide leg, pull-on pants are definitely on the list of style mistakes that can make you look older. Sometimes it’s a matter of comfort. I get it.

But it is possible to wear comfortable slacks and jeans that also have some style to them. And you don’t have to swing the pendulum all the way to the other end and wear the tightest-fitting leggings available.

Instead, look for a fabric that includes a bit of spandex or other type of stretch construction, so the pant leg is a little bit of a leg-hugger. You don’t have to be thin, nor do you have to have perfect, shapely legs to wear slim-fitting pants or jeans.

The key to this style of pant is what you put with it. For most of us in midlife, a tunic style top that is not too clingy along with a flat or low-heeled slip-on shoe will take your outfit from frumpy to fashionable.

Or, create an outfit using a pair of fitted jeans, a short sleeve top, and a longer length sweater. I found a really cute longer black cardigan at Target and I love it.

My sister is a few years older than me, and just recently decided to give leggings and a casual tunic length top a try. And you know what? She looked really adorable and more youthful than the mom style jeans with a shirt and sweater combo she would typically wear.

Here are some examples for you:

Bestseller No. 1
No nonsense Women’s Stretch Denim Legging, Dark Denim, XX-Large
  • All-Day Comfort and Stretch: Experience ultimate comfort and flexibility throughout the day with our…
  • Authentic Denim Look: Get the stylish look of denim with our Stretch Denim Leggings. Featuring faux…
  • Secure and Flattering Fit: Our high-waisted leggings with an elastic waistband offer a secure and…
  • Versatile Style for Any Occasion: From casual outings to trendy outfits, our Stretch Denim Leggings…
Bestseller No. 2
No nonsense Classic Leggings-Jeggings for Women with Real Back Pockets, High Waisted Stretch Jeans, Medium Wash Denim, X-Large
  • Comfort Elastic Waistband: Our Classic Denim Leggings are designed with a comfort elastic waistband…
  • Real Back Pockets: Unlike many leggings on the market, our Classic Denim Leggings come with real…
  • Retains Shape & No Show Coverage: These leggings are not only comfortable but also retain their…
  • Comfortable & Versatile: Perfect for all your fall outfits women love, the leggings are comfortable…
Bestseller No. 3
Leggings Depot Women’s Cotton Blend Stretch Pull-on Jeggings Casual Pants with Pockets (Denim Blue, Medium)
  • Soft Breathable Fabric : Our jeggings casual pants are made of beathable ultra-soft cotton,…
  • Stretch & Comfort : These high-quality denim-like jeggings are a must-have for your everyday outfit….
  • On-Trend : This ideal women’s daily casual pants and work pants style will stand out and shape your…
  • Design & Occasions : These women’s jeggings have a faux front pocket, and a real back pocket for a…
SaleBestseller No. 4
IUGA Jeggings for Women Tummy Control Pull on Stretchy Jeans High Waisted Skinny Jean Leggings with Pockets Trendy Casual Dark Blue
  • 【Stretch & All-Day Comfort】Made from a blend of 40% cotton, 47% polyester, and 13% spandex, IUGA…
  • 【The Perfect Fusion of Jeans & Leggings】Feeling like leggings but looking like jeans, IUGA…
  • 【Pull On Jeans for Women with 4 Pockets】Featuring two front side pockets and two back pockets,…
  • 【Space Saver】Compared with the bulk of traditional skinny jeans, IUGA stretch jeans for women…
Bestseller No. 1
ROSELINLIN Womens Short Sleeve Tunic Top Henley V Neck Blouse with Ruffle Hem Casual Summer Tops XL
  • Material: 95%Polyster 5%Spandex,Comfy Soft,Stretch and skin-friendly tunic top
  • Feature:Womens Casual V neck short sleeve blouse tops, floral print,ruffle design,loose fit,trendy…
  • Occasion: The dressy and comfortable casual tunic top is perfect for daily life, work,…
  • This floral tunic tops perfect for wear with jeans or leggings in spring, summer, fall or winter.
Bestseller No. 2
syoss Womens Summer Casual Tunic Tops Plus Size Short Sleeve Henley Shirts Button Down Dressy Loose Fit Blouse XXL, Black
  • Distinctive Design, Unique Features: This henley-neck tunic stands out with its exceptional design…
  • Supreme Comfort in Soft Fabric: This henley-neck tunic prioritizes comfort with its soft fabric,…
  • Versatile Fashion for Every Occasion: From daily life to work, parties, or vacations, this tunic…
  • Versatile Floral Charm for Every Season: This floral tunic effortlessly captures the beauty of…
Bestseller No. 3
BETTE BOUTIK tunic tops for women short sleeve loose fit tunic tops for women loose fit dressy WhitePink X-Large
  • MATERIAL: 95%Polyester+5%Spandex Fabric with Vibrant Pattern Print are Super…
  • Feature:Short Sleeve,Crew U Neck, Wooden and Muliti Color Decoration Button Front Design,High Low…
  • OCCASION:The Cute Tunic Tops Perfect For Work,Day Casual Relaxing Or Going…
  • Matching:All-Match Clothes,Suit For Jeans,Skirts,Casual Pants Or Shorts;Suitable For Spring,Summer…
SaleBestseller No. 1
Bruno Marc Womens Slip-on Loafers Casual Comfortable Lightweight Boat Shoes, Black – 9 (SBLS225W)
  • Trendy Appearance: Classic and simple loafers, available in a variety of colors. The upper is made…
  • Lightweight Loafers: Each shoe weighs only 6.7 oz, this loafer is very light and comfortable to wear…
  • Versatile Women’s Loafers & Slip-ons: This pair of stylish and comfortable casual shoes is an…
  • Comfortable: Covered with a cork surface, the removable EVA insole is breathable, soft and…
Bestseller No. 2
STQ Slip on Canvas Loafers for Women’s Arch Support Sneakers Comfortable Orthopedic Shoes for Foot Pain Relief Taupe US 8.5
  • Lightweight and comfortable:These canvas shoes are incredibly light, weighing less than five ounces….
  • Improved Foot Comfort: Women’s canvas shoes with removable arch support insoles for improved foot…
  • Dynamic Shock Absorption:Step into unparalleled comfort with our shoes featuring dynamic shock…
  • Versatile and stylish:These lace-up loafers are perfect for a range of occasion, from formal events…
SaleBestseller No. 3
Dr. Scholl’s Shoes Womens Nova Slip On Fashion Sneaker,Black,8.5
  • SUSTAINABLY CRAFTED: Womens slip on casual made with linings from recycled bottles
  • MATERIALS: Womens fashion sneaker available in faux leather, fabric, canvas, mesh, or microfiber…
  • FIT: Womens sport casual loafer with slip-on fit with twin gore panels and padded collar for extra…
  • SUSTAINABLE COMFORT: Comfortable Insole Technology with anatomical cushioning, comfort & support
Bestseller No. 4
STQ Loafers for Women Quilted Slip On Sneakers Casual Comfort Memory Foam Fall Shoes Black 7.5
  • [100% Vegan Faux Leather]: Casual women’s loafers with quilted pattern decorating, made of 100%…
  • [Slip On Closure]: Elastic band on each side with elastic bands for a snug, comfort fit with no…
  • [Designed Heel Shape]: Ergonomically designed heel part, prevents blister and bring you all day…
  • [Soft & Durable Rubber Outsole]: The womens slip on shoes with soft and durable rubber sole and 2 mm…

Now, of course there are going to be exceptions, and I’ll show you an example. There is a way to wear wide-leg pants, be stylish, and have fun.

I recently bought these cotton, wide-leg cropped pants with a crinkly linen top, and really love the look:

how not to dress old

I love the pockets! And, they are very comfortable, too. These are 100% cotton, but you can also get them in linen. That’s next on my list. Both the pants and top come in a variety of colors.

Complete your outfit with a chunky necklace and some flats or sandals, and you’ve created a stylish look.

Here are the purchase details if you want to see more:

find your perfect size with Measure & Made

Hey there friend, do you struggle to find pants, jeans, crops, & capris that fit you well? Yep, most of us have that problem.

Well, take a minute to learn more about Measure & Made, and their unique sizing system called ShapeLogic. Once you find your perfect size, you can buy and wear any of the bottoms on their site and they’ll fit you well!


7 | Shapeless shifts

When you decide that you don’t want to dress old, a shapeless shift that hangs like a flowered potato sack is one little item that needs to be crossed off your list of things to wear today.

Call them shifts, muumuu’s, dusters, housecoats…I think you know what I mean. They usually have flowered prints, which, well, is on this list too.

So a traditional flowered muumuu should stay in the closet (or be donated) for several reasons when you don’t want to wear clothes that will age or date you.

Are they comfortable? I’m sure they are. Are they an option for hangin’ around the house? Of course, they could be. But that’s where they should stay if you’re looking for advice on how not to dress old. 👗

8 | Dated florals

This is a tough one because there are so many floral patterns out there, and not all of them will make you look dated or old.

There are a couple of things we can look at:

  • What is the style of the piece that has the floral pattern on it? If it is a muumuu type shift as discussed above, it falls into the “dated floral” category. Sometimes, an updated style to the piece will lend a more stylish look overall. So, keep that in mind when deciding if a floral print works for you.
  • What type of floral pattern is it? It’s not a black and white “rule”, but many times a small floral print will date your look. Or, a floral that reminds you of your grandmother’s tablecloth might give you pause.

9 | Grandma’s jewelry

I love my mom. She’s 93 and adorable. And, she loves to be fashionable, so the outfit is always put together, complete with jewelry. The jewelry choices include chunky necklaces and brooches.

Lovely for her, but not so much for someone who is trying not to dress old. Leave the brooch in the jewelry box, girlfriend, unless your personal style sways toward the vintage look. Then it could be really cool.

Otherwise, you’ll date yourself with outdated jewelry choices.

p.s. I love you, Mom 💗

10 | Dressed in Black

Some say that wearing all black is a style mistake that will age you. I disagree. I think it depends on what you wear and how you wear it.

Yes, baggy black pull-ons with a short sleeve collared cotton shirt will make you look older, for example.

The most stylish or classic all-black outfit will not enhance your looks if your face is pale and devoid of a natural, healthy glow.

But, a pair of well-fitted black ankle-length slacks with a ¾ sleeve tunic top in a flattering, drapey type fabric, classic jewelry and a cute pair of mules?  That, to me, is a classic, stylish look that is never dated.

It comes down to the fit, fabric and choices we make for each piece.

Decide what works for you.

Here is an example that I put together for you :

You’ll find inspiration from these outfit pieces that you can use to create your own personal look with the budget that works for you.

How to Dress Younger at 60 (or 50, or 70!)

10 Style mistakes that will age you - how not to dress old

Some women could care less if their preferred clothing choices might be considered dated. And I respect that!

If you want to look and feel young in a natural and attractive way, I would encourage you to first take a long look in the mirror and define who is looking back at you.

Because who you see is how you ultimately present yourself to the world. And, how you feel about that woman will always be reflected in your clothing choices, your demeanor, and your confidence.

If you want to know how to not dress old, start there.


Well, we’ve journeyed through the common mistakes that can age us faster than a cheap bottle of wine. But remember, just because we’re mature women doesn’t mean we should shy away from the fashion game!

You see, younger women have their own style battles to fight, but we’ve got something they don’t – experience. We’ve seen trends come and go, we’ve learned what works for our body shape, and we know the importance of classic style.

The best thing about being a woman of a certain age? We’ve earned the right to wear what makes us feel fabulous. We’ve realized that the right size is not just about numbers on a tag, but about how a piece fits and flatters our unique figures.

And yes, we know that well-made pieces are worth every penny. They’re the backbone of any stylish wardrobe and a testament to our personal taste.

So, go ahead. Embrace your age, celebrate your style, and remember – it’s not about dressing like a younger woman. It’s about dressing like the amazing, confident, and stylish woman you are.

Because at the end of the day, fashion is not just about the clothes we wear. It’s about how they make us feel. And you deserve to feel nothing short of spectacular!

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How not to dress old. Avoid Fashion Mistakes that will date you

27 thoughts on “How Not to Dress Old – 10 Style Mistakes That will Age You”

  1. For a New Year’s Day visit to a friends open house I wore a white button down blouse under a black cashmere slip on sweater with a pair of dark skinny jeans. I wore black leather slingback wedges and just a bit of jewelry. This is very similar to my style of many years except the sweater is much longer now. I am very short and very overweight but always take a lot of pains with how I dress. When we got home my husband told me that I looked really nice, and that he noticed me sitting down before we left and thought to himself that I looked really cute. We’ve been married 49 years. This made my day. I also ordered the sweater in 2 more colors.
    I’ve struggled with my weight all my life, so I know that I can’t afford to look sloppy as it translates into very nasty labels that I’ve always tried to avoid. I find that classic pieces are always in style and are generally more tailored so they do not add extra bulk. Oddly enough, when I was younger my style may have aged me a bit but now I find it does just the opposite. I appreciate seeing this blog because I agree that at this age though we have tremendous purchasing power, no one markets to us at all.

    1. I don’t really bother with what’s fashion now because next season it will will be gone. I have my own style which will probably not be to everyone’s style. I’m 63 and love my Dr Martens purple have chunky jewellery my daughter is more conservative, but my 21yr old granddaughter loves it. She took loads of my clothes and jewellery to take to uni. I just think wear what makes you happy, clothes are meant to be enjoyed too my makeup is a lot more muted otherwise I would just look like a clown. I do get lots of compliments which makes me feel even better just experiment.

    2. All of this advice is great. But what if you live in south ga where it is usually in the 90’s and the same for humidity. Long sleeves even in light weight material are miserable and forget sweaters . I am 73 and love to look stylish but sweating in hot clothes is not attractive and certainly not comfortable. So what is the solution other than moving to cooler climate?

      1. Hi Trisha, I understand your situation as I lived in SW Florida, sub tropical climate, for 12 years. I wore sleeveless or short capped sleeves all the time, and no more than 3/4 sleeve when needed. I always carried a lightweight 3/4 sleeve cotton sweater with me, mostly for indoors, as the air conditioning was usually freezing, at least for me. The bottom line for me was, and still is, if the weather/climate calls for sleeveless, that’s what I wear. If someone doesn’t like the look of my mid 60s arms, that is not my problem. I wear what works for me. I don’t know if that is the response you were looking for, but I think you should dress in a way that makes you feel good, comfortable, and stylish, whatever the length of the sleeve.

  2. Hi Margo, thanks so much for sharing the specifics of how you dress and style yourself to your age and body shape. It sounds like your husband was right, you looked really cute! I agree that classic styling is a great choice for many ages and body shapes. Thanks again for sharing.

  3. Your advice about bras is spot-on. All my life I wore unlined, non padded, underwire bras. For some reason I purchased a lightly padded, lined, underwire bra and voila! I looked like I lost 5 lbs.! I’m short (5 ft.) and large chested (36D) and just changing the style of bra I wear enhanced my figure more than I ever thought possible. I just love your blog.

    1. Hi Marie, I’m so glad you found a bra that works for you. You’re right – it’s amazing how it can change your look in a positive way. And thanks for the compliment about the blog, I really appreciate it!

  4. Hi Candi…I just found your site and I am so glad that I did. This was a delightful read and I didn’t want it to end. Such great suggestions!. Thank you!

  5. Appreciate the advice here, but also feel that it’s reinforcement that women need to hide their bodies as we age. So my skin is sagging a bit, but I love this tank top. Shorts cool me down and flower prints make me smile. I think if you feel good, you’ll radiate positive energy that is more beautiful than anything you can wear. Think Frankie in Grace and Frankie. Do you love her as much as I do? She’s the coolest lady going and she breaks a lot of the rules here. Be-you-tiful. 🙂

    1. Hi Tracy, I didn’t create this post with the idea that we should hide our bodies as we age, but rather, do what is appropriate for you as an individual. Many women who read this post are looking for general advice on how to dress in a way that will help them look and feel more youthful. Bottom line? Wear what makes you feel good.

  6. This legging thing is out of hand. If you are wearing them with a long top to cover your bootie, it’s spares eyes being on a body that should not be exposing their butt. As we age, we get too “comfortable” and “accept ourselves”. Sorry ladies, the best fashion advice are the dirty words diet and exercise. Being disciplined about the hangar before the clothes makes choices easier and lighter on the wallet. One more non PC thing, no matter how many overweight models there are these days, it’s just downright unhealthy. Should be #1 fashion tip for mature women. We’re not getting younger, but wiser.

  7. Thank you Candi for info I just found this blog love the advice,
    I’m short 4”11” 65 years young and a little over weight I find that I have lost my style clothes don’t look as good as they used to I’m just not sure what to wear any more I know we can’t avoid getting older but I do want to look stylish thank you for your honest advice greatly appreciated

  8. I am 76 years old, 5’2”, eyes are blue. I used to be petite but life has settled on my tummy. I have dieted,exercised and cried. My biggest pleasure is scarves. A pretty scarf simply tied to hang down the front
    Is my favourite accessory. It gives my figure a distraction which makes me more comfortable.

  9. I am 77, still ski fast ( like 54 mph ), work out , eat right, have great genes , have a badass attitude according to my daughters, and avoid trends. I LOVE pinks and teals and look fab in a strapless or one shoulder according to my college kids. DO YOU!!

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