Any Moms losing their cool factor? It hurts less if you never had it to begin with.
A few years ago I learned that my personality type is most likely to catch fashion trends…on their way out. This explains a lot.
Specifically, why I have never been cool.
To be fair, I didn’t stand much of a chance since I skipped two grades in elementary school – which is every bit as geeky as it sounds.
It meant I was a solid two years younger than my peers. Not a big deal when you are in grade six, but a high school disaster… Imagine changing for Phys. Ed surrounded by well-endowed girls. Me with my washboard chest and twiggy legs. Throw in a baby blue uniform shirt, brown polyester short-shorts displaying a white space to write our names…not cool.
I recall being teased about being flat-chested, and my dear friend Rachel assuring me I would have an advantage for sports. Too bad I was also uncoordinated.
I would have traded in my aerodynamic body for actual athletic ability. (thanks though, sweet Rachel). I heavily relied on my sense of humour to carry me through the rocky bits.
Decades later, why would I dare to hope I could be even slightly cool as a forty-something, four-time producer of human beings?
But sometimes I try. Don’t we all try, sometimes?
Last year my sisters surprised me with a visit to Sephora for my birthday to get a makeover. Since I rarely go out, I gussied up a bit (let me guess – gussy isn’t a cool verb). We chose an approachable young lady to do my makeup and learned she spends 90 minutes putting on her makeup daily. Ninety. In 90 minutes I could serve my kids breakfast, start my taxes and paint the dining room. But bless her, she was polished perfection.
Before she began my transformation I asked if I should take my makeup off. Confused, she tilted her head and leaned in closer. “Oh. You have makeup on?”
Worse yet, in a store filled with bottles of foundation in every shade, she struggled to find even one option in my shade of pale. Apparently Casper is not a common colour.
Not cool.
Yet, after having young salesgirls help me select a few outfits recently, I have started to feel a glimmer of hope in my fashion future.

dear fitting room millennials:
I need you to comprehend the power of your words toward us older Moms.
While we want your honest opinions, treat us gently, okay? Talk to us as if we are insecure middle schoolers, uncomfortable in our own skin. We may be.
Gravity is our new enemy. Wrinkles appear overnight. Our <Mom self-esteem> has taken a few blows over the years. We have been stretched in every way imaginable, but it wasn’t always this way.
When we celebrate Sky High jeggings as a hiding place for muffin tops, pretend you understand.
We will gobble up any ego boosts you offer.
If you tell me my butt looks great in skinny jeans, I am likely to buy them in every fade. I may even tear up a bit because those words are lifegiving to my butt. And to me.
Every Mom truly deserves a win.
When you suggest I not try a smaller shirt size because my arms are really long, it may haunt me. I may envision gorilla appendages and suddenly feel self-conscious. How did I not know my arms were too long for my body?
What else do I not know about myself?
a boost to my mom self-esteem
I recently met a sweet, trendy American Eagle salesgirl who said all the right things.
She had a lovely way of making me feel like there might be hope for me to become trendy myself. I requested her the last two times I ventured out to find an elusive outfit.
She offered honest opinions of which colour brought out the blue in my eyes and made me look less pale.
My sweet millennial chose frayed jeans and stylish shirts labelled Soft and Sexy. I was starting to believe that maybe I could be cool{ish}.
We really connected – peer to peer, breaking past the older Mom to young salesgirl barrier.
I was pretty sure I made a friend.
So when I found chunky, stylish ankle boots in a neighbouring store, I was bursting to show my new buddy. I finally had something to offer her. A hot fashion tip to thank her for her kindness as my stylist.
I’m pretty excited about these boots. They are an amazing deal, just across the hall. Bursting with pride, I continued. And there are many sizes left, if you’d like to pick up a pair.
Ooooh! I think I will, she replied. My Mom would love these.
Not cool.
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Any tips to share below for staying funky and stylish as we age? I’m asking for a friend.
Pour a coffee and sip on more hope and humour.

Karen! You make me smile and truly salts.
Salts! What the. *LOL I guess because I never use LoL unless I do.
That’s awesome! I’ll take smiles, salts and LOLs – whatever I can get. Marc told someone today we would ‘give’ them our extra skates and it autocorrected to ‘gobble.’ No rhyme or reason. ๐
Oh that was hilarious Karen as always!! ๐๐๐ I am currently rocking the โno makeup, glasses, track pants and baggy shirtโ look, but when I attempt โcoolโ again Iโm gonna need the name of that sales girl!! ๐๐๐
Thanks, Andrea. It helps to not take ourselves so seriously, right? Yep – my salesgirl’s a keeper – most of the time. Somehow I picture you pulling off Slobby Chic like no one else could. Until I see proof otherwise, I won’t believe it! ๐
Ugh. I feel you, Karen. I’m rarely in malls, but when I am, I avoid ALL of the stores I used to shop at in my twenties: they make me feel older somehow, whether it’s the sales girls who seem to be bubbly and perfect and never age, or the way the mirrors in the dressing rooms seem to highlight every flaw on my body, or the realization that these clothes are just NOT. GOING. TO. FIT. my Mom bod. Did anyone else’s RIB CAGE get BIGGER after giving birth?! I’ve got the same awkward, gawky youth stories: too skinny (one of my high school teacher’s actually asked if I was eating okay), terrible at all sports (couldn’t make even one school team), tons of flat chest jokes, or worse: am I the older sister of Jesse (my way cooler younger brother). Isn’t it an unwritten rule that older siblings are supposed to be cooler in age alone? I had a makeover DISASTER in my twenties which sent me on the path to realizing less is more.
But Moms ARE cool. In fact, we’re the coolest beings ever! We aren’t supposed to be cool to the younger generation. We already have all the coolness we need: we have our kids ๐ Plus, who wants to waste all of that precious time and energy trying to be cool again? Not me! Thanks for the laughs, Karen.
P.S. I recommend clothing stores you wouldn’t have been caught dead in in your youth: you’d be surprised how flattering a lot of the clothes are now and hopefully the sales ladies are moms as well ๐
Hey Jennie! You and I must have been twins separated at birth. My sisters are way cooler than me too. I thought there was hope when AE started a Mom Jean line. Now they just need to have real Moms helping in the fitting room. But I will remain eternally loyal to them for the butt compliment – I’m dysfunctional that way. Yep – Moms are WAY COOL. Our kids don’t know it, but we do. Maybe we should have shirts made:.
Thanks for talking back to my words ๐
I was shopping in White House Black Market the other day and the sales gal suggested that I try Chico’s instead. Not cool.
Oh my goodness, Kim. Is that even legal? Thanks for feeling the struggle with me!
Oh my goodness Karen this is awesome! I love your writing, I can always count on it to seriously pick me up and make me laugh. Mom of 4 boys here and totally get the need for occasional validation that all hope is not lost for us yet. ๐
Alicia – you are filling up my tank with your sweet words. Let’s meet in real life and throw our EIGHT boys together for some real fun, shall we? Clinging to the hope with you friend.
I thought I was alone… Thank you for giving me hope and humor today! ๐
Oh you bet! Glad this was what you needed ๐
15 years ago, I wore an outfit to church (at this time, I was only 23, but already married 3 years and had a one-year-old son) and the most stylish teen at church complimented me on my outfit. No joke! That outfit is still folded in a little pile in my closet! Years later, I told her mom that story. It turns out that that sweet little teen is now the one struggling with self-esteem and her mom was going to share that with her to give her a boost! It’s amazing what words can do for us…and for others through us! Let’s not forget that the girls who spend NINETY minutes on makeup each day are probably struggling with self-esteem too!
Love this reminder of the power of our words, Wendy. That you still remember that encouragement from so many years ago. Thank you.
Karen,
You are seriously one of my favourite writers in the world and I can’t wait until you release your NYT bestseller.