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The One Characteristic Every Stylish Woman Has in Common

July 27, 2021

Hello, and welcome to Dressed for My Day! I’ve been tossing this concept around in my head for a while now and I thought it was time to type it out. Like you, dear reader, I’m constantly learning. My own personal style continues to evolve. And, even as I learn more about my personal style, I’m also navigating aging. In the process I study other women a lot. And I especially pay close attention to those women who seem always to look smart and pulled together no matter what the occasion may be. How do they do it? What sets them apart? They all dress differently, these beautiful, stylish women. But I’ve discovered that every stylish woman has one common characteristic.

Courage the One Characteristic Every Stylish Woman Has in Common

It takes courage to be stylish. And while it may seem to us that some women just are courageous and others aren’t, I’ve decided that this is one character trait that we absolutely can develop with perseverance. In fact, we’ve all had to be courageous at one time or another.

As I wrote previously in this inner beauty post on courage, I’ve found that it takes a large dose of courage just to be a woman. Wouldn’t you agree? It takes courage to:

  • earn an education
  • apply for a job
  • say, “I do”
  • carry an unborn child
  • birth a baby
  • raise a child
  • pay the bills

Yes, we have to be braver than we really are to meet the bare minimal requirements for the lives most of us live. But you and I know that none of us live “bare minimal” kinds of lives.

We need even more courage to:

  • say goodbye to a stillborn child
  • nurse a husband through illness
  • raise a child with special needs
  • live as a single woman in a couples’ world
  • care for a parent with dementia
  • bury a child
  • love a difficult family member
  • persevere in a strained marriage
  • forgive a wayward spouse
  • recover from an injury
  • rebound from a divorce
  • battle cancer
  • endure multiple military deployments
  • move across the country
  • love a child through mental illness
  • confront a boss who is demanding inappropriate things
  • blow the whistle on a perpetrator
  • live with an autoimmune disease
  • walk away from a dream to deal with a reality

So you probably have more courage than you even give yourself credit for. But do you have the courage to be a stylish woman? I think you do. I think I do, too. We can tap into the courage we’ve had to have for life’s challenges in order to make the courageous decisions necessary to be stylish women.

A stylish woman courageously determines her own personal style essence.

When we’re growing up we are largely influenced by the style choices of our mothers, other influential women in our lives and our peers. Our personal style is shaped by these women. And there’s nothing wrong with that. Who shaped your sense of style?

Casual Summer Looks for Mother & Daughter
Me and my daughter Abigail // See the original post HERE.

But if I want to be a truly stylish woman I must choose to chart my own course at some point. And that takes courage. I’ve noticed that the most stylish women dress in a way that resonates with their personality, lifestyle and season of life. Their style “fits” them. That doesn’t just happen. It requires courage to break away from the pack and determine your own style.

Exercise in courage: Take the time to jot down some notes about your own personal style. Use descriptive words to define how you like to dress. Be sure to note the signature clothing items, colors, style hacks and accessories that make your style your own.

If you need a little helping determining your own personal style, check out my post, How to Define Your Signature Style.

A stylish woman courageously dresses the body she has now.

As we age we sometimes discover that our bodies change, too. While I’m all for staying healthy and fit through proper diet and rigorous exercise, I also have noticed that truly stylish women come in all shapes and sizes. It takes courage to remove from your closet things that no longer suit your body shape or proportions. Some of those items may have sentimental value or maybe you just hope for the day when you can “get back into them.” But a stylish woman ruthlessly focuses on dressing the body she has now.

Leather Sneakers
See the original post.

Body acceptance takes courage. But it’s not just about accepting our bodies; it’s about celebrating them by continuing to dress beautifully even when we feel like we’ve “lost” some of our former beauty or shapeliness. A stylish woman ages with grace because she accepts that some changes are inevitable and she develops ways to work around or with those changes.

Exercise in courage: Note how your body has changed in recent year. Be honest with yourself about those changes. Then determine if you’ve done anything to adjust your wardrobe to better fit your new body. Are you buying the right size garments? Have you had a bra fitting recently and purchased new bras? Are you wearing your clothes differently, not to hide or disguise your body, but to accentuate the positive?

A stylish woman courageously wears the colors she loves and feels her best in.

I’m all for having your colors analyzed, if that helps you to feel your best about the style choices you make. But I think it’s even more important to narrow down your wardrobe colors so that you build a wardrobe that really works for you. And when you do narrow down that color palette, I think it’s going to serve you best to choose colors that make you feel your best. When we wear the colors we love, we show up as our authentic selves. Joy exudes and confidence comes more naturally.

How I Dressed Wednesday
I LOVE wearing black. It makes me happy. So this dress makes me feel good and helps me put my best foot forward. Shop the look HERE.

Truly stylish women create wardrobes that help them wear the colors they love. They have the shoes, handbags and accessories to put together outfits in the colors they love over and over.

Yes, stylish women pay attention to the trending colors. But they make conscientious decisions about whether or not they will wear those trends. They have the courage to break their own rules and wear those trending colors if they so choose, but they also have the courage to stay in their own lane if they’d rather.

Exercise in courage: Put together your chosen color palette for the fall and winter. Consider the colors that elicit compliments when you wear them and the colors that are trending this year. But courageously lean into the colors that bring you the most joy and make you feel like you.

A stylish woman courageously allows her wardrobe to evolve.

Well, some of us do better with change than others. But stylish women don’t allow a fear of change to keep them stuck. They realize that, while they may love the silhouettes, cuts and patterns they are currently wearing, beautiful style is a healthy and lively mixture of the classic and the current. These women resist the pull to get stuck in their ways and bravely venture into heretofore untested territory.

Eileen Fisher Lantern Pants button cardigan

It’s scary trying new things, or at least it is for me. But when I reflect on how much fashion has evolved over just my lifetime I realize that change is inevitable. And sometimes when I examine those changes through the rearview mirror I realize that my fears kept me from enjoying styles that I later came to appreciate.
Post from November, 2018. See the original post HERE.

In fact, I was quite late to wearing skinny jeans. But once I tried them and got used to the feel of having denim hugging my legs, I wore little else. It took me a while to figure out what features to look for and how to style them for my body shape and proportions. And it took courage for me to wear something that felt so different from the boyfriend and bootcut jeans I had become accustomed to. But, like riding a bicycle, wearing skinny jeans eventually became second nature and required no bravery at all.

What about you? What trends were you slow to try that you later enjoyed?

But this type of courage is not just about bravely trying trends…

Modern Summer Work Outfits 17
See the original post HERE for shopping and styling details.

Stylish women courageously allow their own personal style essence to evolve, even if ever so slightly, as times change. The best example of this that I can think of is from Downton Abbey.

If you’re a fan of the original series, you surely observed how the fashions worn by the Crawleys and their peers changed over the years spanned by the story (1912 – 1927). The only “upstairs” character whose style did not change was the Dowager Countess of Grantham, played by Maggie Smith. And sure, the Countess dressed beautifully, but not stylishly. As the years passed, her floor length (often with a train), lace covered taffeta dresses looked more and more out of step with those worn by the other more stylish Crawley women. A stylish woman courageously allows her personal style to evolve, even if the changing of times feels a little unsettling.

Exercise in courage: Look back at photographs of yourself in the past ten years. You’ll certainly see that you have aged. That’s inevitable. But do you also recognize that your style has evolved? Note how it has changed over the years. Allow those subtle changes to boost your courage as you consider how your style may need to evolve even more now.

A stylish woman courageously tries the trends that pique her interest.

But let’s go back to those trends for a minute. Because it does indeed take courage to try new trends. I’ve discovered that stylish women don’t necessarily try every trend. In fact, embracing every trend out there could lead to a sort of style schizophrenia. Ha! There’s nothing stylish about being too trendy.

See the original post for shopping and styling details HERE.

But our style can’t evolve without trying some new things, too. And every new style is going to feel like a fad when it first surfaces. I’ve noticed that stylish women pick and choose the trends they try, leaning into those that feel the most authentic to their personal style, those that line up with their way of dressing.

For instance, over the past few years my personal style has become more relaxed and a little more edgy while still staying somewhat true to my original classic style roots. I enjoy combining classic elements with more modern pieces. And I like selecting classic pieces, such as blazers, t-shirt, jeans and black pants, in more modern iterations. So it feels authentic to me to try the relaxed fit denim and casual blazers. I’ve enjoyed experimenting with different types of footwear with these trends, too.

Blazer and Jeans
Shop this current look HERE.

But it wouldn’t feel authentic to me at all to purchase a lot of the beautiful embroidered or crocheted pieces that have been trending in the past couple of years. These lend more to a bohemian or romantic style. And the puff sleeves, ruffles and smocked bodices are also more of the romantic style essence. So I haven’t really dabbled in those trends a lot either. And honestly, when I have, they didn’t feel right, so I didn’t wear them much.

Stylish women courageously choose which trends to try and which to pass on. I’m not always good at this, but I’m trying. What about you?

Exercise in Courage: Prepare to see lots of trend reports as we head into fall. Evaluate them not just based on your first reaction, but on how they would incorporate into your personal style essence. Encourage yourself to try at least a few of the ones that you decide would help you look like a more modern version of your preferred style aesthetic. THEN be prepared to bravely face a little push back, even from surprising sources. Don’t let it frustrate you. Consider the source, listen intelligently to any sound criticism or advice, but sift through it, too. Also determine to try new things multiple times, giving yourself time to acclimate and get the styling right. Most of us don’t style new things perfectly the first time.

A stylish woman courageously celebrates and enjoys other women’s styles without feeling threatened by or antagonistic toward them.

As I mentioned, I haven’t worn a lot of the ruffles or puffed sleeves that have been trending recently. But that does not make those trends wrong, bad or ugly. In fact, I love them! On other women, that is. I truly do. I admire women who wear big puffed sleeves and ruffles and bows. I admire women who wear tops with cutouts in the shoulders and across the chest (another HUGE trend!). And I celebrate women who confidently wear lots of color.

Easy Summer Outfit for Women Over 50
See the original post for shopping and styling details HERE.

But that’s just not me…

And sometimes I take some criticism for not wearing more color, more ruffles, more cutouts, what have you. Maybe you’ve faced similar criticism from a well-meaning sister, daughter, husband or friend. But I believe truly stylish women courageously stay in their lanes…without getting angry or defensive towards women who are in a different lane, style-wise, that is.

You see, stylish women have a high degree of grace about them. Wouldn’t you agree? They’re not just dolled up to look nice on the outside, but they have an aura of grace about them. They appreciate good style and don’t define it simply by what’s in their own closets.

Exercise in courage: Think of someone who dresses differently than you do. Not someone who doesn’t put any effort into her appearance at all, mind you. But someone who makes different style choices from yours. What do you appreciate about her style that is different from yours? Next time you see her, courageously tell her what you love about what she’s wearing or how she’s styled her hair. Let her know you truly admire her taste even if it’s different from yours. Now don’t turn this into a backhanded compliment. Know what I mean? Don’t let it feel more like an insult. Graciously affirm her.

Finally, a stylish woman courageously wears her wardrobe with confidence and enjoys it.

Maybe this is the hardest step of courage to take. Somehow truly stylish women show up consistently with confidence in their style choices. Whether they’re sitting a trend out or embracing it, wearing a new color or no color at all, donning a new dress or one they’ve had in their closet for years, these women walk into a room exuding confidence. And truly stylish women don’t just have an air of know-it-all confidence. They have a joy that translates as confidence. Know what I mean?

Fit and Flare Dress
See the original post HERE for details.

Honestly I think I’ve decided that this brand of confidence comes from an inner disposition that has very little to do with what they’ve put on. Instead, I suspect that these stylish women have put ample thought into what to wear and how to wear it but, once they’ve put it on, they’ve turned their attention outward and off of themselves altogether. They’re able to bravely walk into a room with little thought to whether or not they “look okay” because their focus has shifted from self to others. They’re more concerned with helping other people feel at ease than with making sure that they are seen. And they’re more inclined to give compliments to other women than to solicit them from those they encounter.

Summer Hospitality with Talbots
See the original post HERE for styling details and shopping.

This type of courage is an ethereal quality that is somewhat hard to define, but we know it when we see it. Right? So how do we capture it? I think stylish women do the work up front so that they can get dressed each day with confidence and then forget about it. They’ve defined their personal style, chosen their pared down color palette, decided with confidence which trends they’ll try and which they’ll let pass, and put together a wardrobe that works for their bodies, their season of life and their lifestyle. And then they just get dressed for their days. They don’t have to overthink it. And that leads to joy and a beautiful self-confidence.

Exercise in courage: How self-conscious do you feel when you walk into a room of people? Do you think more about how they perceive you or about how you can serve them or make them feel more at ease? What steps do you need to take so that your wardrobe is one that works for you so that you can enjoy using it to get dressed for your day rather than focusing too much energy or time on it?

If you need help creating quick outfits so that you don’t have to dwell on your appearance too much, check out my 7 style formulas.

Give'm Lip!
Most items are no longer available. See the original post HERE for details.

Look, I don’t mean to imply that courage alone equals style. Obviously there are other qualities that stylish women have. Many are gifted with an uncanny ability to put things together in an aesthetically pleasing way. Others have amazingly beautiful bodies to work with. Some are trained in fashion or other arts. And others have the money to purchase clothing that could make a rag doll look drop dead gorgeous. Ha!

But while some stylish women may have some of those things, I truly believe all stylish women have a modicum of courage. And I also believe we’ll never look really stylish without it…even if we have lots of money, a beautiful body and a college degree in fashion design. Yes, it takes courage to have great style. And that is one thing we can work on developing. How do I know? Because you and I have needed even more courage to do so many other things in our lives. We are courageous women. So I know we can do this little thing with courage, too.

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Blessed for My Day

The Bible teaches us that our confidence in the Lord can grow as we become more sure of who He is and what He can do. That surety comes from reading the Bible consistently and thoroughly, reflecting on and thanking God for answered prayers and living in community with other believers who are doing the same things. As we get to know our God – His character and His ways – our faith in Him develops into a strong force that helps us navigate the hardest of times.

How is your confidence in the Lord? Do you have more doubts or convictions? What do you need to do to strengthen your faith in God? Consider one action – reading more of the Bible, spending more time in prayer or attending a Bible teaching church – and act on it this week. As your confidence in God grows your courage in life will grow, too.

Now faith is the assurance of things hoped for, the conviction of things not seen. ~ Hebrews 11:1

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xoxo, Kay
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33 thoughts on “The One Characteristic Every Stylish Woman Has in Common

  1. What an excellent post! Thank you Kay, you’re always interesting to read. I’m a Work in Progress. And the word courage resonated. And walking into a room, and concentrating on others, not comparing oneself, is definitely a learnt skill and ultimately one that brings peace. Enjoy your Summer, and I shall think about what colours I’d like to wear for Autumn.

  2. So well put, I’m also finding style is geographical. Where I live people comment on how plain I dress but when we visit a larger city for dinner, shopping etc, or visit my daughter who lives in D.C. I seem to fit right in. I often find I want to adjust my style to my surroundings, which in the end is uncomfortable. Like you, with all the ruffles, puffs, and patterns I’m wanting clothes that are minimalist, classic, but I do love a little edge (My favorite piece of clothing is a leather jacket from Madewell) and lug sole boots are calling my name for the fall. I just purchased some black platform Gizeh’s Birkenstock’s and can’t wait to wear them. Lastly, whew, I love black, but I always feel I have to be apologetic for wearing it. There’s something so cool, calm and collected about a black outfit.

  3. This was a beautiful post from a beautiful, courageous woman! Thank you so much for taking time to share such important words for women! You are truly making in difference and impacting women!
    God Bless you, sweet Kay!

  4. WOWZA! This was a GREAT post! I found myself “amen”ing you all along the way! Lovely and CoUrAgEoUs post, sweet sister!

  5. Oh Kay -another “hit it out of the ballpark” post! I would agree whole-heartedly that stepping out in style takes courage. The risk is to come across as trying too hard, being fussy or self indulgent. That’s where you address that a truly stylish woman can put an outfit together that suits her style essence, enter a group, and use her inner skill to make others feel comfortable, draw others out gracefully, take the focus off herself. I loved your idea of looking at pictures over the years. While I have clothes in my closet from 10 years ago that still fit, that isn’t anything to be proud of if they make me look dowdy and dated. Time for some thinking, purging, and wardrobe evaluation! As always, another great BFMD. My prayer journal is full of your wisdom!

  6. Such a great post, Kay. This resonated with me on so many levels. Thank you so much! You always speak with such grace and wisdom.

  7. What a wonderful post, Kay, reminding us of how courageous we are as women. Our courageous nature has had to surface during these difficult COVID times. And, we’ve also had to be courageous in many ways dealing with life situations each day for many years. This message came at just the right moment for me. Not only because of situations but because of my learning to become more courageous within myself in order to select styles and colors that I love. Yes, not relying on all the outside voices! Yesterday I cleaned out my closet and donated all the not right for me clothes. This message just reaffirms that I’m definitely on the right track.

  8. Excellent post! It was a great reminder to keep doing what we’re doing, and for the right reasons. Worthy of a second and third read!

  9. I agree with everyone here saying how wonderful this post is.
    This paragraph especially resonates with me: “Think of someone who dresses differently than you do. Not someone who doesn’t put any effort into her appearance at all, mind you. But someone who makes different style choices from yours. What do you appreciate about her style that is different from yours? Next time you see her, courageously tell her what you love about what she’s wearing or how she’s styled her hair. Let her know you truly admire her taste even if it’s different from yours. Now don’t turn this into a backhanded compliment. Know what I mean? Don’t let it feel more like an insult. Graciously affirm her.”
    Because I believe we should get inspiration from everyone, not just validation!!
    You have such grace in your words Kay, and thank you for being so open.

  10. This is a really great post. You hit on personal reasons we choose to wear what we wear and what/who influences us.
    I would be considered a plain dresser by most standards. No ruffles and loads of jewelry for me. I don’t follow trends that look silly on me. Fit/ color and the occasion are my main concerns when dressing. These pieces last and do not go out of style. I buy the best quality I can afford. I wear the clothes they don’t wear me.
    Robyn’s post is so true. Different regions have different styles.

  11. This is the most beautiful post from the most beautiful and courageous woman. This post has been the most encouraging to me. You truly have the gift of encouragement. I so appreciate your posts. I have implemented many of your suggestions and get compliments each and every time I do. Your suggestions are so spot on. Thank you for sharing your gift with others.

  12. Well said!

    I have meant to comment on your chambray drawstring and white shirt outfit, which brings up good memories of my grandmother who would wear just such an outfit. My grandmother was very pretty and slender, had your coloring but not your height, wore beautiful clothes, and knew how to stay cool!

  13. This dear heart ❤️is why your blog is miles ahead of other fashion blogs. You care about the women you try to help. We sense that you really want us to feel good in our choices.
    I have a SIL who has lion courage so when she lost her hair to chemo, I was not surprised to see her embrace cute turbans and just get on with things. We have more courage than we know. I found that courage when my husband died. Trust yourself and get on with it.

  14. What a great post! Made me stop and think about the changes I have made since I was in my 20s. I never used to wear T-shirts, but I wear Graphic tees under blazers now. I never liked capris when they first came out but since it was a trend I did wear them for a few years and was OK with it. Now I don’t really care for them. I have the same thoughts as first, that they made me look shorter.
    Now I really like ankle pants, I think they look better on me. But I still like more fitted pants. I do wear a lot of dresses in the summer because I think they’re cooler. I never used to wear jeans that much only once in a while but I do like them now that I am retired but only in the cooler weather, they are too hot in the summer for me. I still love the Blazers, always have. And leather jackets. Always will. I don’t mind trying a trend or two once in a while but I like my style, which I am told sometimes is dressy, but that is me.
    Great blessed for my day! You always hit the nail on the head. The Bible tells us to be Bold, I believe this is part of being courageous. God bless

  15. Thank you, Kay! What a thought provoking and encouraging post! You never cease to amaze.
    God has blessed you with grace and wisdom.

  16. Thank you, Kay for this post! You are my favorite blogger because we have a similar style (not ruffles or puff sleeves) and shop at the same stores. I resonate with your statement about doing the work up front so that one can enter a room and then focus on others. This is what I try to do.

  17. I took my style from Kay when recently in my new town I was invited to a bday bbq in the heat…. so I decided on a vneck black tee and olive utility pants and slip on camo sneakers. All things I had for this spur of the moment outing. I wore a tiny star gold necklace for good luck and did my nails. Im 71 and widowed so I went alone and had fun….. I was comfortable and felt good.

  18. You did it again! I love this post. You addressed the ways we can be stylish which are excellent, but having confidence is number one. Whether we wear a sweatshirt and sweatpants or a ball gown we should display confidence. It’ll be the first thing people notice. Thank you for being in touch with your audience and giving us great advice. I also love your writing style – it’s so open and friendly and makes you relatable. Thank you!

  19. A Great Post Kay!

    I feel I am that person who has confidence when I walk-in a room. I feel good in what I am wearing.

    I am not sure I could wear a shorts jumpsuit…. Never say Never! Lol


  20. This post was amazing – and true! Thank you for encouraging women to be courageous in their style.

    The BFMD hit the mark as well. ❤️

  21. Excellent post Kay! Thank you so much for sharing your heart. I love your hair in the photo where you’re wearing the black dress! All of the photos were outstanding. The one of you and your daughter, so precious! Thank you for being so faithful in helping us to improve ourselves in a Christ-centered way!

  22. What a great post! I am finding the courage to re-define my wardrobe in a new stage of life – retirement. You have been a real inspiration, Kay! You are stylish, but also classic and I get so many great ideas from you. I also appreciate your Christ-centered outlook.
    I am also learning it takes courage to try new trends, even when others close to me (like my husband) don’t necessarily like them – like the half tuck. But as I have told him many times, my style isn’t about him – I do it for me. 🙂 He gets it.

  23. Thank you for reminding me of all the ways that I am already courageous! I tend to consider myself to be a “scaredy cat” so this was very encouraging! I found your blog and videos fairly recently but you have already influenced me to try some new styles and to realize that I deserve to have a nice wardrobe. I know that I can focus on the needs of others when I feel confident in my own style. You are a blessing!

  24. Wonderful post! You inspired me to look again at my choices to see what is working and what is not. And when I don’t get it right to evaluate and make the change(s) needed.
    Clothing myself with the Lord Jesus Christ is a similar process and when I’m dressed that way, one that is attractive to others.
    Thank you for your inspiration and encouragement.

  25. Such a perfect post! Courage – just what I need right now. Lots of it! You also look so beautiful in all these pics! True confessions, I’m printing many of them so when I have my next haircut, I can show my hairdresser so she can copy yours. It’s fabulous! I also love the pic of you and your daughter. Love you, Kay! Hope you have a great week!