How to Dress Stylishly at Any Age – 5 Steps

How to dress stylishly at any age

Today we are discussing 5 Steps for Stylish Dressing at Any Age, because a reader asked me to write about dressing stylishly without looking like a teenager.  She noticed that some outfits featured on What I Wore Wednesday looked a bit too youthful for the women wearing the outfits.

Now, she promised she wasn’t talking about me, but she didn’t pinky swear or anything, so I can’t be sure.

mismatched clothes - at least she's not too matchy-matchy

Fashion is subjective and when you start giving rules for style and clothing, women get a little tense.  Throw in a chat about aging and there’s no telling what will happen in the comments.

Hopefully we can navigate this tricky subject with grace and a good dose of humor.

We’ll see.

5 Steps for Sylish Dressing at Any Age

5 Steps for Stylish Dressing at Any Age


Step 1.  Dress Modestly


Once my husband was talking to a woman in the church parking lot and while she was bent over digging through her purse,  her boob fell out of her shirt.

My friends, that should not happen.

Lock and load the girls as Stacey and Clinton say.  Buy a bra fortified with rebar.  Do whatever you gotta do, but keep the girls tucked neatly in your shirt.

I don’t think I’m a prude.  I try not to be, but less is not more when it comes to fabric.  Sometimes more is the path of least resistance.

I think that sometimes, as we age, we tend to try a little too hard – we plunge the neckline a little lower, plaster on a little too much makeup, over do the hair a bit, all in an effort to feel better about ourselves.

Girls, give yourselves a break.

Wear your laugh lines and droops, sags and bags with pride. You’ve been blessed.

It’s a privilege to age.  Not all girls are fortunate enough to make it to forty or fifty or sixty.

Do what you can to spruce up the outer woman and then live life with joy, because it’s the inner beauty that will shine through and attract others.

When I think of modesty, I generally think of necklines, hemlines, fit (as in tightness), and the overall impression of the outfit.

Forgive me for being crude, but certain outfits scream hooker.

I know you know what I mean.

The mall is full of stores that display outfits once reserved for street walkers.  Some of these looks can even be quite stylish and I’ve even seen them show up at school functions. Hoochie Mama & Hussie Bullseye

And let me admit that it’s tempting to push the limit of what is good and pure.

I know.  I shop in the same stores you do.  I try on the same clothes, and sometimes I even look good in them, but I know they wouldn’t honor my Lord.  I also think they would be disrespectful to my husband and a bad example to my kids.

None of this is new to you.  I know you’ve already got a handle on modesty, but I felt like it should be included in this type of “chat”.


Step 2.  Wear Clothes that Fit


In my closet hang clothes ranging from size 6 to 12, small to large.  They all fit.

I truly believe size does not matter.

Try things on and don’t lock yourself into one size.  Good fit is way more important than a number.

Unfortunately good fitting clothes aren’t always easy to find at a low price-point.

I shop in the Walmarts and Targets of this world too.  Sometimes their clothes just aren’t made correctly.  Don’t beat yourself up over it.  Move on.  There will be a great pair of fitting jeans in a different store.  You’ll live to find another cute dress.  Trust me.

I think it’s better not to have something than it is to have something that doesn’t fit; however, I don’t always take my own advice.  So, yes, I make unwise purchases from time to time too.

If you’re going to spend money on anything, buy a good fitting bra.  It’s the most important thing you wear, especially as you age.

I know they are expensive.  You can pay $25 dollars (on sale) and up for a descent bra, but do it.  If you can only afford one, hand wash it and wear it out.

Clothes fit different when you wear a good bra.  They will make you look younger.


Step 3.  Dress for the Occasion


Once, at a Flag Day ceremony in town, an older woman showed up in spandex workout pants and a workout bra/tank with a plunging v-neck.

Many a twenty-something wished they had her body, but people smirked and whispered.  They chuckled behind her back.

She was dressed inappropriately.  It was an outfit for the gym and not a Flag Day ceremony hosted by the Boy Scouts.

Now I’m going to say something and some of you are going to hate, but you just go right on hating for a minute.

Pajamas are for bed, not for grocery shopping, trips to the doctor, or running errands.

As a society, we’ve become slovenly and that spirit seeps into every aspect of our lives.

I do believe what we wear is important.  It changes how we feel about ourselves and how others view us.  We will get and lose opportunities based upon how we are dressed.   What we wear reflects the respect we have for ourselves and also the respect we have for others.

We are worth the time to get dressed.  Our husband and children are worth the time it takes for us to look presentable, pretty even.

We confuse the verse that talks about God looking on the inward man.  God does see what’s within.  He’s looking at you and not what you’re wearing, but man is looking on the outside.

Let’s not be fooled.  What we wear matters a great deal.


Step 4. Wear Trends in Small Doses


I think this is the key to not looking too youthful as we age.

I like trends.  The skinny jean trend I can live without, but that’s just my hips talking.

I’ve heard the rule that if you wore a trend once in your life, you can’t wear it the next time it becomes fashionable.

I disagree.

Take neon for example.  I wore it in the 80′s and I wore lots of it – on my shirt, in my hair, up and down my arms…my shoelaces were neon for goodness sake!

Can I wear neon now as an adult?

I can in small doses.

Most mornings my daughter walks out the door looking like a billboard for multiple personality disorder.  I think that’s fabulous.  Young people need to be creative and explore all kinds of fun colors and prints.  People actually look forward to seeing her in an animal hat and zebra stripes.  She’s young and it’s fun.  She can wear head-to-toe trends and it’s perfectly acceptable.

I can wear trends in moderation.

Maybe I’ll carry a neon bag or choose a shirt with a neon stripe.  Perhaps I’ll buy a neon watch and wear it all kinds of fun way.

Trends are good.  They keep things fresh and get us out of our ruts.

Just be careful.

Wear the next hottest fashion with caution, because a little goes a long way.

Step 5.  Be a Role Model


Recently a teenager was over my house and she told me that she loved my style.

It was a great compliment to me, because I want to model fashions worn appropriately.

I want to be in-style and modest.  Trendy and purposeful.

People are watching us and you never know who, so while you’re dressing to please yourself, think about the girls who are looking up to you, searching for a woman to model themselves after.

And a word of caution (here comes the haters again), no young person is going to look up to you as a fashion role model if you’re always dressed like a fuddy-dud.

It’s ok to be comfortable and super casual at times.  It’s ok to skip every trend that hits the runways, and no big deal if you’re wearing clothes from three years ago.  I am too!

But, put some thought into your wardrobe, because what you wear says something about you.

Fuddy-dud looks a lot like grandma jeans and baggy t-shirts, but in the church, it looks like beat-up denim skirts worn with dirty sneakers.

I hope we can still be friends.  Don’t throw tomatoes please.

I don’t know the first thing about fashion and I’m just beginning to navigate the challenges of aging.

My heart is not to offend or mock or put you down.  I want to encourage you and lift you up.  I want you to enjoy life and have fun with fashion.

I think fashion is a gift to us.

Do we ever outgrow playing dress-up?

Enjoy fashion.  Embrace trends and be happy with yourself.  Work on the inside and the outside will automatically improve.

About a year ago, I wrote on a similar topic.  It had ten tips though.  Good grief.  I was wordy that day!  If you’d like to read it, click HERE.  Also linking to Musings of a Housewife’s Fashion Friday HERE.

This post is my opinion.  Don’t give it more value than it’s worth.



  1. abozza says

    I think my job helps me dress appropriately and fairly stylishly. When on break, I can often be found in sweats, pajamas or jeans and a ratty t-shirt. I do like the way I feel when I look good, however, so I know it’s important for my self-image, and the image I project to the world, to look nice. I just love my comfort! :)

  2. says

    I love this post. I’m so dissatisfied with my body and trying to lose weight {which seems to be a never ending battle that I am losing} so I have not bought much new lately. I wear basic jeans and tees or sweaters. I have to go buy some new things for spring/summer and I so wish we could go shopping together. I need style…

    • says

      Deanna my Sister, I don’t want to trivialize your concerns about your body, but I think one of the worst aspects of women is this self-criticism that keeps us from being our best RIGHT NOW. From your pictures, you seem to have beautiful skin and hair and a lovely smile. I myself am definitely “chubby.” If you see photos of me to the contrary, it’s cuz I only pick the ones where I look my thinnest ;-) My principles says, “wherever I am, I want to be my best.” Because frankly, I have no idea when and IF I’ll lose all this weight and I don’t want to wait for that time that may be a long time a-comin’! :-)

  3. says

    What a great post! Lots of great advice!! Proper undergarments are key! I agree with you on bra and go a step further and say find underpants in a proper fit and fabric for what you’re wearing. Also, I think this generation has forgotten what a slip is! They are crucial for smoothing lumps, bumps, lines, and fighting static cling on fun tights.
    Go undergarments!! k, i’m gonna stop ranting and just end saying that you look lovely and are a perfect role model for a real women dressing and living in the real world. truly beautiful

    • says

      Laura, I totally should have had you write this post instead of writing myself. You are SO much more qualified to talk about these things than I am. You’re right about the panties. To be honest, I have a terrible time finding the right fit and comfort. I also never, ever know what size to buy.
      And the slip thing – I stand guilty as charged. I do happen tot think you’re a right though. I need to invest in one.

      Thanks so much for sharing your thoughts. They are always welcomed and very appreciated.

  4. says

    Great tips, great perspective, great points all. I’m such a fan of your blog! And, thanks to you, I’m finally exploring scarves (and even the odd pair of sort-of-skinny jeans) at the ripe young age of 43. Stay classy ;)

  5. says

    AHHHH!! okay… i need to read this again tomorrow.. for the pure humor. nowhere can i read a post about hookers, fuddy-duds, a boob falling out and your hope that we don’t throw tomatoes in 1 single post. seriously — you are amazing and i agree with EVERY SINGLE THING YOU SAID!

  6. says

    There is so much amazing in this post Tricia. You have hit the nail on the head with each point you made.

    As one who used to think of her body as the only source of her beauty, I know what it is to be desperate for something that is flattering. My goodness are those girls (myself included) so wrong.

    The most beautiful and flattering women are confident, gracious and humble. Countenance is timeless. As a mom living in a not-so-uppity area of the city, I am often smirked at for being dressed in things other than my pajamas. seriously! but i don’t believe becoming a mother takes away our liberty to shop our own closets. I love jeans, a tunic and a huge scarf. Or tights, a tunic and a huge scarf. I pretty much wear the same thing everyday and I feel lovely.

    I also feel well-prepared to chase my toddler, who seems to have more agility than a rabid squirrel these days…

    great post sister :)

    • says

      Kristin, I live in a pajama wearing area too. I know. I intentionally under-dress for just about everything, but still, the only pj’s I wear are in the house. ;-)

      Countenance is timeless…what a great statement. You are SO right. I need to remember that.

  7. says

    LOVE IT!!! I’m no fashion guru at all but I agree with all of this…especially the pajamas in public! And in my opinion…no part of the boob should be seen at church even if standing straight…ever! lol Sadly I’ve seen it more and more lately. :)

  8. Natasha says

    Confession: I was the one who wrote that comment. See I knew you can handle this topic in best way possible. All I have to say is Amen to all of the five tips. I’m soon to be 23 and never wore skinny jeans because I became a mom 7 weeks before my 22nd birthday and skinny jeans make me look like a teenage unwed mama. I know I started dressing a little different after having a baby.

    • says

      Well, thanks Natasha. And thank you for stepping up and asking the question. I very much enjoy knowing what my readers are thinking and what topics they would like to read more of, so I appreciate you.

  9. says

    Love. This. Post!!!! You had so many little gems that packed a punch in this piece, Tricia. Loved this one: “Do what you can to spruce up the outer woman and then live life with joy, because it’s the inner beauty that will shine through and attract others.” Amen to that! So helpful. So funny. You are a gem, yourself!

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