10 Things I Want My Daughters to Know About Dressing Themselves

Rudey Maliszewski

At preschool drop-off, another mom pointed out,”Your daughter’s socks don’t match.”

I turned my palms upward in a je ne sais pas and wrinkled my nose, “Rough morning. Can’t win ’em all.”

My then four-year-old was Little Miss Mismatched. She loved Disney princess dresses paired with rain boots and purple flowered leggings with her green and gold Packer t-shirt.

That morning, I picked my battle.

She walked into the kitchen dressed in a thin ballerina dress and no tights. I shook my head, unh-uh. It was January. In Chicago.

Without tears, she marched back to her bedroom to change. This time, she dressed in weather-appropriate clothes, but her socks didn’t match (one Minnie Mouse, the other mini Dalmatians, and polka-dots).

Mismatched? Pheh. Not a battle worth fighting.

Now, at five and eight, many of our conversations are about fashion and what people are wearing. I mostly give my girls free reign selecting their outfits because I love their fearless sense of style and the random pairings that look unintentionally chic.

Now is the time to lay out our values. Now, before they are teens and tune me out and their friends in.  I want to encourage my girls to express themselves, yet not without guidance.

10 Tips for My Daughters on How to Dress Themselves

1. Dress for You and You Alone

There will be pressure to follow trends worn by your peers. It’ll be tempting to emulate Taylor Swift or Selena Gomez. Know this: I love and accept you for you. Please stay true to your personality and embrace your individuality. Pick your clothes for the right reasons: What makes you feel comfortable? What makes you sparkle?

Feeling good about yourself on the outside has an impact on your confidence and how you feel on the inside. Looking good, feeling good, right?

2. Find a Signature Look

Uncover your inner French girl and develop your personal style. Train your eye to spot a look that sings to you. When you’re shopping at a store or in your closet, ask yourself: Does this shirt add a pop to my step? Do I walk a little taller, smile a little brighter when I’m wearing this dress? Do I love it? If so, you’ve landed on a keeper.

Rock your style with confidence and no apologies. You are beautiful if you’re dressed like Princess Elsa or the singer Lorde. Be true to yourself.

3. Be Mindful of Dress Codes

How you dress for school is different than how you dress for the daddy-daughter dance. That one you know, but there will be many more rules for dressing, and they’ll probably shift as you age (like smart casual and business casual).

You’ll need to consider the setting, the culture, and even the country. Then you’ll need to know how to code switch. If you’re uncertain about what’s appropriate or inappropriate, ask someone you trust (You can always pick me. I’ve got your back, girl.)

4. It’s Important to Know What Not To Wear

Let’s chat about the runway outfits and the awards show glam in US Weekly. Let’s pore over In Style together and talk about what’s in, what’s out, and why?  This way you know how to prevent your crack from peeking out of your jeans. No whale tails, sweetie. If you aren’t yet familiar with the term, let’s keep it that way.

You’ve been begging me to get your makeup done at Macy’s, and we’ll do that on a mommy-daughter day. It’s complimentary, yet you are expected to buy a product. I’ll spring for that $20 palette of eyeshadow if you go halfsies. I know that sometimes an expert’s opinion will resonate more than mine. I’ll smile because I’ve been you. I remember.

5. Make Sure Your Logo Matches Your Mind

What do you want to say about yourself? I know, I know, it’s just words on a t-shirt, but I read them, and so did the boy sitting next to you in math class. If you’re wearing a shirt that says, “I Call the Shots,” do you know what that means? Do these words speak to you?

Remember two things: Words are powerful and please, please stay away from the sweats that say, “Luscious” or “Juicy” on the booty. Just say no.

6. Clothes Conversations Are Loaded

Your school’s rules and your ideas may not always mesh. The standards and restrictions of dress are not always equal for boys and girls. Why is that? Let’s discuss and I’ll teach you how and when to speak up. This documentary on dress codes titled Shame: A Documentary on School Dress Code may be a good launching point. I’m missing the boat on why you can’t show your collarbone too. It’s a school, not the Vatican.

Then again, I wore a uniform from first grade to senior year and following the code was not my forté.  I crushed a lot of Pepsi cans in detention for dress code violations because I rolled my skirt too short and never tucked in my Oxford.

7. Judgers Are Gonna Judge

Within a split second, people will decide whether to trust and respect you based on what you’re wearing and their personal bias. Should it be this way? No. What a wonderful world it would be if we all sought first to understand each other, but it’s not always the case.

This topic feels a million years away and boy, I’m not ready. But times flies. We’ll need to talk about butts, boobs, and bellies before you hit middle school. Be aware of how much skin you show when you’re not at the pool – boys can’t control themselves (I’m kidding…sort of).

8. Let’s Talk about Clothes, Baby

Right now you want to pull together outfits on the iPhone app Fashion Story.  You want my input on outfits and often ask, “What girl do you want to be?”

Timing is everything; I know that. Soon you may be in a more vulnerable mindset, especially when you’re trying on jeans or getting dressed in the morning. I’ll aim to talk to you when you’re chill. I want my message to be well-received, so I’ll try to refrain from giving my opinion unless it’s a what-not-to-wear (again, no whale tails!).

9. You Can Be My Personal Stylist

I know you’re always watching me as I apply makeup and hot roll my hair. You’re in my closet as I prepare for a date night with dad. Your consultation on how I look – both wow, mom and ooooh, no – and our open dialogue are teaching you savoir-faire to find your voice. My hope is in sharing myself with you at an early age; it won’t feel one-sided when I make suggestions about your clothing choices.

10. Boundaries are to Guide, Not Control

I’m providing a foundation when you are young so we have a long history of open conversations and to set the stage for the stickier ones that will come sooner than I wish. I have non-negotiables: no tattoos or body piercings until you’re of age.

Your choices have been age and weather-appropriate.  I love heels, and you know my rule: You can step out in style when we go out to dinner, but not at school. At school, you need to wear tennis shoes. When it comes time to make your case on hair dye, we’ll negotiate. When it comes to the tattoo, even if the words are “soo meaningful” and written in some exotic script, I won’t budge. I wouldn’t even try your dad; he stands with me.

Love you to the moon and back,


Head to the Family Room



This post was syndicated with permission to BonBon Break Media LLC.

Roots to guide and wings to fly – that’s my motto. Bienvenue! I’m Rudey. I’m a writer and an elementary French teacher living in Chicago with my husband and two daughters. My aim is to have fun while slowing down, growing roots, and building a solid foundation. It’s also to strengthen our wings and soar. Stop by Rudey’s Room and let’s connect! Follow Rudey on Rudey’s Room and Facebook | Pinterest| Instagram