How Not to Dress Old
Confidence and Style Fashion

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

(Last Updated On: May 1, 2020)

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.

Many of us are quite comfortable doing things, including putting outfits together, the way we’ve done them for years. It worked in the past, so it must still be the right choice, we think.

Well, maybe not so much.

Let’s take a look at some style mistakes that aren’t helping us look our best!

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How Not to Dress Old

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.

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.

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.

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.

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.

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:

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.

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Decide What 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.

Candi Randolph Midlife Blogger


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

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6 COMMENTS

  • Margo

    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.

  • Candi Randolph
    AUTHOR

    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.

  • Amy Johnson

    Great advice, TFS!

  • Michelle

    Great post, Candi! I came to leggings due to fibromyalgia. I like the comfort. But soon discovered the leggings and tunics were great for my middle-aged figure. Win-win!

    Michelle
    http://mybijoulifeonline.com

    • Candi Randolph
      AUTHOR

      Hi Michelle, absolutely! It’s a great look, stylish, fun and oh-so-comfortable!

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