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How to Dress Your Age…Beautifully

January 14, 2019

Now settle down. I know the title of this post is the kind that can provoke some women into a tizzy before reading word one. But if you proceed to read with your defenses up, you’ll miss the true intent of my words and the spirit with which I’m writing them. I have no intention of telling you you must or cannot wear or do certain things once you’ve reached some specific age or season of life. No, this post isn’t a list of fashion dos and don’ts for the older woman.

However, the truth is that as we age and our bodies change, we are wise to make a few adaptations that will help us look our best. By all means, do what you want. Wear what you please. But don’t refuse wise counsel just because you don’t like to be told what to do.

How to Dress Your Age Beautifully

As I’ve gotten older I’ve had to change many of my behaviors. I’ve had to adapt how and what and when I eat. I’ve started wearing reading glasses and I turn on the close captioning when I watch some television shows and movies. I stopped running long distances and took up other exercise forms instead. You know, now that I think about it, I wrestled against each of these changes. But in the long run I’ve done what I needed to in order to thrive.

In the same way, we absolutely can wear whatever we want as we get older. We can style our hair how we wish and continue to wear the same makeup shades if we choose. But it just might be in our best interest to consider some adjustments.

So what I’m offering us today are style principles that will generally help the older woman – the woman whose body shape, coloring, skin, hair and other elements of appearance have changed – to look her very best. Hey, maybe you haven’t changed at all. But I have. Most of us have. Let’s allow these principles to guide us as we select what to wear, how to wear it and how to style our hair and makeup so we can be confident and beautiful women.

Style Principles for the Older Woman

#1 – Make sure your style has evolved.

Are you stuck dressing the same way you did in a different season of life that you’ve now outgrown? Take the time to determine your personal style for this season of life.

Ask yourself if your wardrobe suits your current lifestyle, body shape and climate? Does it feel current? Also, make sure your hair style and makeup have evolved. If you’re still wearing the same eye shadow or styling your hair exactly the same as you did 20 years ago, it might be time for a change.

Nothing will age you more than looking like you just stopped somewhere along the way. 

#2 – Instead of trying to look young, aim for looking modern.

Another thing that will make you appear older than you really are is looking as though you are trying too hard. Don’t you agree? When you see a woman who looks as though she is trying to look young, she actually ends up looking even older than her years.

Instead of trying to look like you’re in your 30s or 20s or whatever, simply try to look current, modern. Absolutely wear your classic, timeless pieces if they’re still stylish and in good condition. But add some modern touches that communicate that you know what’s current. For instance, in this outfit pictured below, I’m wearing simple jeans and a classic caramel sweater, but I’ve added modern touches with a square silk scarf in the season’s colors and leopard print flats.

Caramel Pullover and Silk Floral Scarf
comfort denim jeggings // caramel sweater // floral scarf (similar) // handbag // leopard print flats (similar)

#3 – Decide what you want your style to communicate and say it clearly.

When we’re young it’s perfectly normal to experiment with style on a daily basis. A young woman can wear a conservative dress one day and dress like a punk rocker the next, and we think little of it. But when we’re older we want our style to communicate a consistent message. Otherwise, we appear unsettled and uninformed.

That doesn’t mean your wardrobe has to be boring and monotone. For instance, if you want your clothing to say that you are interesting and hard to pin down, then you might wear a variety of color combinations and artsy accessories. So no one is suggesting that you have to wear a uniform.

Then again, consider this. The great writers are the ones who found their voice and stayed true to it. You or I could read a few lines of Shakespeare or a few paragraphs of Hemingway and know immediately who wrote them. Likewise, those who know such things, could easily identify the music of the Beetles, the photographs of Ansel Adams or the paintings of Claude Monet.

Fickle experimentation is acceptable and even attractive in the young. But the seasoned woman, like the true artist, is expected to know her style and stick with it confidently.

Have you found your style voice? Take a moment to reflect on what you want your clothing to say, and then say it every time you get dressed.

#4 – Don’t hide behind your clothes; let them frame you.

As we age and go through so many body changes, it’s tempting to just throw in the towel and dress in a way that keeps us in the shadows.

Resist that temptation. And don’t buy into the notion that you can no longer bare any skin either. In fact, a bare clavicle is beautiful and alluring. So go ahead and wear a flattering v-neck, but draw the focus to your face with pretty earrings and soft makeup.

Powerful Black Dress
Black dress  (similar) // earrings // leopard foldover clutch

Look, we can all spot someone who is hiding. And that kind of insecurity is not appealing. So instead of trying to stay in the dark, choose clothing that puts you in the best light…and shine.

#5 – Fit is more important than ever.

A young woman can get away with wearing oversized tops and baggy pants. She can even look stylish and cute in them. But as we get older fit becomes even more important. When your clothes fit correctly you communicate that you know what you’re doing and who you are. You look like you’ve put your own clothes on and not someone else’s.

But as our bodies age, they also change in shape and even proportions. So make sure the clothes in your closet actually fit the body you have today. Invest in a good tailor if necessary.

#6 – Under garments are top priority.

Good under garments are important for every woman really. But as we age, things shift. Ahem. So it’s all the more important to lift “things” back up to where they belong. Make sure you replace your bras regularly and that you get a professional fitting. When wearing body hugging dresses, skirts or even slacks, wear the appropriate under garments that will smooth and shape.

You don’t necessarily have to wear under garments that reduce your size by hugging you in tight. You may be done with that! But you can find garments today that at least smooth out and prevent lines and bumps.

#7 – Quality becomes more important with age.

Once again, younger gals can just get away with more. And we all had our day in the sun when we could wear “any ol’ thing” and look beautiful. But as we age, we do better to wear pieces of higher quality. Here’s why. Clothing of lesser quality tends to age faster. The fibers wear, the colors fade, the trends change, etc. And as the clothing begins to look old and more worn or dated, it just makes us look older, worn and dated, too.

On the other hand, timeless, classic clothing made of higher quality fabrics will continue to look fresh and current longer. So when we wear it, we look current, too.

Where specifically should you invest in more quality pieces? Start with handbags, shoes, coats and jewelry.

#8 – Insist on comfort and joy.

The good news is you don’t have to wear anything you don’t want to. In fact, you need to insist that your clothing and shoes feel comfortable. Every single thing you wear should be something you could wear all day if you had to. And since you can find comfortable dresses, skirts, jackets, pants, shoes and jeans these days….with a little patience…this is doable!

But don’t just settle for comfortable. Also insist that your clothing bring you joy. Wear pieces that make you happy. When you feel good in your clothing, you’ll look like you are comfortable, both in your own skin and in your clothing. And your confidence will put others at ease.

#9 – Spend more on shoes.

Unfortunately, now is not the time to skimp on your footwear. As we age, many women experience problems with their feet, legs and even back that require them to wear shoes with better insoles, support and padding. So do what you need to do in order to keep your feet and the rest of your body healthy and strong.

But don’t go frumpy either. Look, there are plenty of good, orthopedic shoes available these days that are both comfortable and stylish. You and I know, however, that they tend to cost more. It’s better to have a few pricier pairs of shoes that are both functional and fabulous than to have a boatload that are only one or the other.

Shoes can make or break an outfit. Shoes can also make or break your body! Spend the time and money necessary to have a few pair that make you look and feel fabulous.

Comfortable Shoes and Summer Dress
dress // sandals // crossbody bag

There’s absolutely nothing wrong with wearing comfortable sandals with your cute dress!

#10 – Adjust your colors as needed.

It’s more important than ever to wear beautiful colors. Especially worn up top and around the face, colorful clothing can actually brighten and change the coloring of your skin.

But as we age, we grey. Not just our hair, but our skin and our eyes even begin to fade or “grey” a little. With this change in color tone, we may need to change the vibrancy of our clothing so that it flatters rather than overwhelms. Ask a friend to help you or even engage a professional stylist to see if perhaps you’d look better in navy instead of black. Or maybe your skin would look better in browns instead of grey.

For instance, I get a lot of compliments when I wear this bright pink sweater. But if you look closely you’ll notice that this fuchsia sweater is “heathered.” It’s intensity has been softened, making it a good choice for my older skin, hair and eyes.

How to Style a Cashmere Sweater for the Office
cashmere sweater // scarf (similar) // earrings

#11 – Stay out of the junior department.

If you’re shopping in the junior department or the retailers frequented by teens, you’re probably shopping in the wrong place. And it will show. Clothing created for teens and women in their 20s is designed for a different body and life season. So even if you’ve been shopping in the junior section because the clothing is cheaper or it “fits” your smaller frame, you might want to find a store more suited to your more evolved style…and body.

#12 – Structure is your friend as you soften.

One of the realities of aging is that many of us “soften” over time. Our cheek bones lose their definition, our shoulders round and our mid sections plump. Ha! Yuck. Just keeping it real.

But an easy remedy for rounded features is structured clothing. Pointy lapels on jackets, crisp collared shirts, tailored bodices and structured cardigans will give you more definition. And more definition will make you look more present, more confident.

No, that doesn’t mean that you have to wear structured clothing all the time. There’s certainly room for the bunchy, soft sweater in your wardrobe. Just be aware of the swap off you’re making so maybe you can add a little structure elsewhere if desired.

#13 – Let your hair down.

One of the easiest ways to look younger is simply to loosen up your hairstyle a little. Tight curls or severe styles age us. But soft curls or free flowing waves look youthful and healthy.

You absolutely do not have to color your greying hair if you do not want to. And you absolutely can wear your hair long if you wish. But the key is healthy hair. Have your hair trimmed regularly and invest in shampoos and treatments that help your hair stay healthy and beautiful.

#14 – Soft, natural makeup will serve you well.

Yes, absolutely continue to wear color on your face. But this might be a good time to soften the shades. And it may be time for another makeup lesson, too. Your face undoubtedly features wrinkles and fine lines you didn’t have a decade ago. Ultimately you want to achieve a soft, natural look that communicates that you’re not having to try too hard.

If you do want to wear a dramatic eye, then go subtle on the lips. And if it’s a day for bright red or pink lipstick, keep your eye makeup soft and subdued. One more thing. Frost accentuates and brings attention. So, since you may not want to invite that kind of scrutiny, matte shadows and blushes may be a better choice.

#15 – A classic wardrobe is the most flattering across the ages.

When in doubt of your own personal style, go classic. Classic clothing looks beautiful on every woman, regardless of age. However, classic clothing can also easily edge into the frump zone. So keep your classic clothing modern and current by accenting with trending patterns, colors and accessories.

#16 – Beware of youthful extremes.

This is where I may get some push back. No, I’m not going to suggest that if you wore it before you can’t wear it again. But we do need to be aware that embracing extremely youthful trends can be a little tricky, if not doomed. Why? Because when an older woman wears things like overalls, grunge, hard rock, jumpers or boho looks, she can look like she’s wearing a costume.

So if you do want to wear a girlish trend, tread lightly. You might want to “practice” wearing it around the house first until you can wear it confidently and effortlessly. Also, balance out the youthful piece with more classic garments.

What do you think?

Do you shudder at the thought of adapting your style as you age? You know, it’s not really a matter of rules or restrictions. As I’ve researched this topic and thought it through, I’ve realized it’s more a matter of developing a little style wisdom. Across the ages, the most beautiful thing a woman can wear is a little confidence. And when we notice a woman who looks like she’s trying too hard…to look young, to look trendy, to look hip…we sense a lacking of that beautiful element.

But when our clothes fit…our bodies, our lifestyles, our personalities and our season of life…then we look more confident and comfortable in our skin. And that’s a beautiful thing.

I’d love to hear your thoughts!

Blessed for My Day

It may be fun to throw caution to the wind and do as we please, but when we follow wise counsel we actually fare better. The Bible teaches us that wisdom, indeed, makes us beautiful women. Today, fashion aside, let’s choose to grow in wisdom. Let’s be women who listen to sound advice, seek biblical insight and wait for good teaching. Let’s value wisdom and ask God for it. Wisdom is one element of beauty we can actually gain more and more of as we age.

Hear, my son, your father’s instruction
And do not forsake your mother’s teaching;
Indeed, they are a graceful wreath to your head
And ornaments about your neck. ~ Proverbs 1:8-9


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xoxo, Kay
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34 thoughts on “How to Dress Your Age…Beautifully

  1. Great post, Kay! I have been struggling with some of these as I quit coloring my hair, stopped working at my husband’s office, etc. I have entered a new season in many aspects of my life. I appreciate your tips!

    1. You know, Lori, I think when we refuse to adjust we just end up looking a little silly. It is hard, though! Thanks so much for reading. Blessings!

  2. Great tips and thoughts. I love fashion and have struggled with watching myself age but I agree with you, I learned to give up some things that just do not work for my “aging like a fine wine” self! Have a great day Kay?

    1. Right, Deb! Aging isn’t a bad thing. It’s just a fact of life. We change. Thanks so much for sharing your thoughts! 🙂

  3. Great advice Kay. You’ve obviously researched and thoughtfully put together this list and I totally agree with everything you said. The classic style has carried me through many years (77 to be exact). I’m trying to age gracefully but stylishly and I love your blog and all of the advice you share with us. Have a blessed day and glad you are feeling better.

    1. Hi Sondra. Yes, I read a lot of other people’s suggestions and opinions, thought through those carefully, tried to think of how they played out in real life fashion sense and went from there. I really do weigh my words here. Thanks so much for your comment. And yes, I’m doing much better today. 🙂

  4. Excellent, Kay, and presented kindly and lovingly for your readers! Your suggestions are perfectly sound and helpful. Thank you for having both the courage and the tact to broach this topic.

    1. Ah, thanks Jan. I never really know how my words are going to come across. Thanks so much for commenting. Blessings!

  5. I see this post as something I will revisit in the future as I age. Life does give us seasons. I think embracing them as we go along is a beautiful thing! This post helps me to consider my wardrobe as part of that process. Your points are reminders to present myself as I really am at this point in time and to be comfortable with that image. Great post!

  6. Good advice spoken with love. I’m 71 and love fashion and I have made some mistakes along the way, but I want I to feel confident in what I’m wearing and not look like a teenager or even a 20-30 year old. I’m in the process of growing out my gray hair and actually like it. Might have to change my makeup color though. All part of evolving. Thanks for wise counsel.

    1. Yes, evolving is the key. When I came upon that concept in some of my research it felt like a breath of fresh air. We don’t like rules, but when we’re advised to evolve that somehow sounds more positive and beautiful. Thanks so much for pausing to comment, Wanda. Have a great day!

  7. These are SO great Kay. Especially evolving. I think our minds evolve as we grow and learn, and so should our style.
    I feel like I’m way more bold in my clothing choices now that I’m older. Not that everyone should be, but it’s my change in thinking. When I was young, I wanted to blend in instead.

  8. Thank you, Kay, for your well thought out & wise suggestions. I truly appreciate this article & have begun to accept more & more “aging with grace”. You certainly emulate that.
    Most of all I remind myself of 2 Corinthians 4:16…..
    Thank you, Sara

  9. This is a very timely and much needed topic! Thank you for being courageous enough to confront it Kaye

  10. Thank you for sharing, Kay! These are excellent bits of wisdom that I will refer to often! I love it when you speak honestly about these “aging issues”. It’s difficult to find good advice and I’ve come to trust you as a wealth of sound suggestions! I also appreciate your classic style!

  11. I agree! I totally think it’s about dressing the body you have now, not the one from years ago or the one you wish for. Dress the one you have now in a way that suits you now, and fit is definitely the key. Older women in baggy clothes tend to look frumpy, not the same cool vibes young girls give oversized items. B