How to Dress to Please Yourself: Dress with Confidence After 50

Last Updated on March 31, 2024 by Candi Randolph

Do you dress for yourself? You know…wear what you want because it pleases you? “Well of course I do!” you exclaim. “Doesn’t everybody?”

But think about it. Stop and really ponder the question, and look a bit deeper, inside yourself, past the initial “of course!” that may spill from your lips.

how to dress for yourself

As women in midlife we expect to be confident and self assured. After all, we’ve lived all these years, we should know what we want, right? But it isn’t always quite that clear cut. That’s why we’re going to talk about how to dress to please yourself as a woman over 50 and dig a little deeper.

Consider the last time you were clothes shopping. It doesn’t matter what you were purchasing. As you were flipping through the options and choices, what thoughts were going through your head?

I’m going to guess that for many, there were some conflicting voices in your head, telling you that:

  • The item under consideration was too casual / formal / bright / sheer / you-name-it, according to someone other than you.
  • Your spouse / family member / friend / co-worker / committee member / you-name-it, may not approve of your choice
  • If you buy that item, you won’t look young enough / pretty enough / slim enough in the eyes of others.
  • Someone your age wouldn’t wear that item.

I know I’ve done it. I’m in the dressing room (which, by the way, was designed by someone who went to great lengths to find the harshest, most unattractive lighting ever created in the entire world) trying on my potential purchase, and in my head I’m going through the litany of negatives about how I look in it, should I wear it, is it the right size, am I too old for the style…blah blah blah.

I think it happens automatically. My mind just goes to the critical self talk. What’s up with that?

I’m in my 60’s and should be well past that kind of negative self talk. And I am, for the most part. But I have to tell myself to stop…and I do. Thank goodness.

How to Dress for Yourself with Confidence After 50

self confidence tips and dressing to please yourself after 50

Ultimately, you know what you like when it comes to style. We all have our own unique style, and it’s about more than what you wear.

  • Our style IS an expression of who we are, and if we let others influence that, we’re not being true to ourselves.
  • Our style IS NOT determined by what happens to be in fashion at present. If it is a look or a color that you absolutely love and you feel beautiful wearing it, then awesome for you! But just because someone says it’s a thing…it doesn’t have to be a thing for you.

When I decided to become a midlife blogger, the whole ‘fashion’ thing gave me pause. I think it’s because when I think of the term blogger, I automatically zoom to someone who writes about beauty, fashion, hairstyles and the like. And I’ll be honest, I enjoy looking good, and I expect it from myself.

But I’m not a fashionista, you won’t see oodles of photos of me on my blog, modeling the latest fashion, or telling you how to put an outfit together in every post.

I see some other very successful bloggers who do this, and am thankful that they’re out there for the women who are searching for that direction. If you’re someone who loves to wear the latest fashions, that’s awesome. That is who you are and you’re honestly dressing to please yourself. Cool.

I know that I’m not that type of blogger. I’ll throw out my two cents about style and putting a look together because I really enjoy it, but that’s not the focus of this site.

We all have unique styles and preferences as well as unique shapes and sizes. We’re tall, short, thin, plump, petite, plus size…and everything in between. So when it comes to being comfortable with our style and clothing choices, there is no standard, no correct answer to pleasing ourselves with our wardrobe. It is our decision.

Try this exercise. I’ll go first.

Create a quick list of what you enjoy wearing. Don’t think about it, just make the list. Here’s mine: 

blue jeans (form fitting, not too baggy), leggings, t-shirts, tunic tops, round or jewel necklines, anything black, very casual shoes with low heels or wedge, capri’s, 3/4 sleeves, lightweight sweaters, comfy clothes (yoga capris and, you guessed it…tank tops) for lounging or working out, with business casual slacks, long sleeves or a dress on occasion

This is me, it’s what I am comfortable in and what I wear. Because…I dress for myself with what makes me happy.

Many women my age wouldn’t dream of wearing a short sleeved or sleeveless top and exposing their upper arms. There’s this thing called crepey skin that is not very pretty, and it happens to us all as we age.

Yes, I have some of that, but you know what? At this point in my life, I’d rather wear the short sleeved top and not worry about the crepey upper arm skin. That’s me dressing to please myself. If you don’t like the way my upper arms look, don’t look at them.

If you were honest when compiling your list, this is your view of yourself and what you pleases you. Whenever possible, choose to wear what you enjoy, what pleases you.

Grab your FREE printable, How to Dress to Please Yourself, and keep these inspiring tips handy!

You’ll find it in the Resource Library under ‘Fashion’:

Three Keys to Dressing with Confidence

Having the self confidence to create your own personal style

When we think about self-confidence for women over 50, one of the biggest challenges I often hear about is how we perceive the shape of our bodies. As we age, our bodies naturally go through changes, and it can be a struggle to embrace and love our bodies as they are. From the weight we may have gained over the years to the increase in wrinkles and sags on our faces, these physical changes can sometimes impact our self-esteem.

However, it’s important to remember that our bodies are a testament to the lives we have lived and the experiences we have had. Each wrinkle and mark tells a story, and it’s a beautiful reminder of the wisdom and strength that comes with age. Embracing and loving our bodies as we get older can be challenging, but it’s a journey worth taking. It’s about recognizing that beauty and confidence come in all shapes, sizes, and ages.

So, let’s celebrate the uniqueness of our bodies and the incredible journey they have taken us on. Let’s focus on nourishing our bodies with love, gratitude, and self-care. It’s time to embrace our bodies, appreciate the beauty within, and exude confidence from the inside out.

1 | Remember that you are in control of what you do and how you look.

At the end of the day, it’s all up to you! How you want to dress and define your style is totally in your hands. Fashion is a great way to express yourself and make choices that truly reflect your personality and preferences. Of course, it’s natural to consider the opinions of your spouse, partner, or friends, but don’t forget to prioritize your own satisfaction too!

Looking back on my own experience, I remember how important it was for me to consider my husband’s opinions and preferences when choosing my clothes and outfits. But, I also wanted to stay true to my own style, so finding that balance was key. Thankfully, he totally got it and supported me, understanding the value of my individuality and my happiness.

In the end, fashion is all about self-expression. You have the freedom to choose what makes you feel confident and comfortable. So, go ahead and embrace the opportunity to create a style that truly reflects your unique identity and brings joy to both you and your loved ones.

2 | Make sure that you are comfortable from head to toe

Whether you are going casual and hanging around the house, heading out to run errands or dolling it up for an evening out, make sure that you are comfortable from head to toe. And that means more than just making sure your clothes fit comfortably.

3 | If you’re doubting…stop

Whether you’re chilling at home, running errands, or getting ready for a fancy night out, it’s super important to prioritize your comfort from head to toe. And when we say comfort, we’re not just talking about clothes that fit well and feel cozy.

It’s also about picking the right shoes, choosing accessories that match your style, and paying attention to all those little things that add to your overall comfort and confidence. So go ahead, enjoy the bliss of feeling comfy and effortlessly stylish in every part of your outfit, no matter what the occasion!

And, if you’re doubting the choices, the look, the vibe, even the hair…STOP and do something about it. Change whatever it is that is not pleasing to you, because if you don’t it will affect everything you do for the duration of the activity.

Give yourself the gift of self-care, knowledge and renewed confidence with The Fashion Cure, an email series course that will take you by the hand (well, in a manner of speaking ) and give you the tools and resources to rediscover your Personal Style in midlife.

Conclusion: The Bottom line

Take a moment to stand in front of the mirror and ensure that you are not only satisfied but also comfortable with the reflection staring back at you. Embrace the fact that your body shape may not fit society’s idea of ‘perfection’ and acknowledge that your hair might need a trim or that it’s time to start exercising again.

Remember, this reflection is uniquely you. Choose to wear clothes that not only reflect your personal style but also bring you joy and make you feel your best. When it comes to self-confidence for women over 50, it’s crucial to dress for yourself, prioritizing your own happiness and well-being. Trust me, you’ll never regret it.

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22 thoughts on “How to Dress to Please Yourself: Dress with Confidence After 50”

  1. Thanks for this timely reminder, Candi. I’ve been thinking a lot lately about cleaning out my closet (as in getting rid of anything I don’t love) and buying a couple of new outfits for spring. When choosing, I will be thoughtful about what truly pleases me.I know at this point in my life, comfort is king. I want to look good and be confident, but I must also feel physically comfortable.

  2. I love that you know who you are. So many of us try to pretend we’re the better version of ourselves. my better version looks amazing in Capri skinny pants…but the real me feels more confident in jeans πŸ˜ƒ

  3. Thanks for encouraging us to be us, and strategies to help us figure out who we are. Fashion is an artistry, and even though trends come and go, we each have our unique style.

  4. Yes south Florida girl here! Shorts, tank tops, shirts with sayings, jeans. I’m not one to dress up really at all unless a certain occasion! Such a great post love it!

  5. Thank you for this post! I need to remind myself that my style is really MY style.. I think too often we think about what other people will think of our choices. I needed this reminder!

  6. Thank you for this timely reminder. It is so important to learn to live life on our own terms and not just based on other people’s opinions or desires.

  7. It’s so important to be comfortable in your own skin! This article inspires me to take a closer look at my own style and to not hesitate to wear those things I love love love. I worry a lot about whether I’m too old for a particular type of outfit, but it’s all about what feels RIGHT.

  8. Great post Candi! I’ve learnt to always dress to please myself. There’s nothing worse than making a purchase that just hangs in the cupboard or stays in your drawers or you do wear but feel extremely uncomfortable or frumpy in it. I need to feel comfortable in the outfit and that it flatters me – if I don’t have both those things, I won’t wear it. BTW – I’m a jeans, t-shirt and bare feet girl around the house too! πŸ™‚ #TeamLovinLife

    1. Thank you for stopping in to read my post, Min. You’re right, those fashion decisions that make me scratch my head and wonder what I was thinking then I made the purchase end up in the donate pile!

  9. I’m a barefoot around the house in Summer gal and socks in Winter. I don’t dress to impress when I’m home in my comfy yoga pants, but I do try to make an effort when I walk out the door. I always dress well enough that I wouldn’t be embarrassed to bump into someone while I was out doing my errands. Being a fashionista bores me – being nicely turned out is what I’m all about.

  10. Yes I definitely dress to please myself and to feel good and I don’t ask anyone for their opinion when I am shopping. I know what suits me and that’s what I work with. Crepey arms? They lift my coffee cup and my wine glass – what else can I ask of them πŸ˜‰

  11. Would like to see mix and match minimalist clothing colors and styles
    I have way to much clothes and want to downsize without losing style
    H e l p

    1. Hi Ellie, I can relate to having too many clothes in the closet! One way to accomplish a more minimalist style is through utilizing a capsule wardrobe. I have a series of posts on the subject and this is the first: If you check out that post you’ll find links to the other three. Hopefully you can get started on paring down the wardrobe while still keeping your personal style intact.

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