It’s a very special Mother’s Day edition of the Everyday Style School Podcast! In this episode I share lessons I’ve learned from my mom, and some of our listeners share style lessons they learned from their moms, too.

In lessons from Linda, I share the story of a style lesson that stuck (for way too long)

In Vocabulary we discuss the difference between ankle, crop and capri pants, and then answer the question “But where are they supposed to hit?”

And in philosophy, I share the best parenting advice I’ve ever received!

Your homework for this episode is to think about the style lessons you learned from your mother, and decide which to celebrate, and which to let go of. Also, think about the lessons you want to your daughters to learn. Plus, there’s some fun extra credit!

“A Mother who radiates self-love and self-acceptance actually vaccinates her daughter against low self-esteem” -Naomi Wolf.

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Read the full episode transcript below! – Ep 48 Style Lessons I Learned from My Mom

The Summer Capsule, and with it the opportunity to join our exclusive All-Access Membership, is coming on June 2. Get your free Mini Capsule Guide, and get on the waitlist for the full Capsule in June.

Hey There! Welcome back to the Everyday Style School podcast where we believe style can be easy, and getting dressed should be fun! I’m your host, Jennifer Mackey-Mary, and today, we have a very special Mother’s Day edition of the show.

I’m going to be sharing a few style lessons I’ve learned from my mom, but last week I asked our community members to share style lessons they learned from their own moms and you’ll be hearing those throughout the show.

A big thank you to everyone who sent in messages–I loved listening to them, and I hope you all do too! By the way, I did not ask them to say nice things about me, or the Capsules. I was not fishing for compliments, but I’m always happy to get them!

Today, In Lessons from Linda, I’m sharing the story of a Linda who heard her mother’s voice in her head for years.

In Vocabulary, we’re answering the question what’s the difference between capris and crops and ankle pants, once and for all.

And in Philosophy, I’m sharing wisdom from my own mom.

Before we get started though, your homework from episode 44, which seems like an eternity ago, was to organize your laundry and clothing care space and supplies. If you didn’t do it yet, that’s ok. But this is a task that will save you time when you’re taking care of your clothes, and money because your things will last longer, look better, and need to be replaced less often. Once you did it, come share it in the Style Lounge.

Let’s Kick things off, as we always do, with Lessons from Linda

I really wanted to share a Linda Lesson with you today about a client who had a super positive story to tell about her style relationship with her mom. I did not want to start out on a negative note–but here’s the thing. I don’t have any stories like that.

I do have one about a mom and two daughters I shopped with, and they were all so nice to each other and so supportive, that I asked them to adopt me. But as far as a lesson goes, they weren’t working through tough stuff–and maybe that’s the lesson.

But, when I think back to all the women I’ve worked with who have a valuable lesson to learn about the impact of mother on her daughter’s style it’s mostly red flags and cautionary tales.

And so while I couldn’t start the show with a super fun happy Linda story, I chose one that at least had a happy ending.

My session with today’s Linda started as a gift. If you’ve followed me for a while you know I really hate my services to be given as a gift. I feel, no, I know that when a woman is ready to feel great about herself, my products and services can be life changing.

I say that without ego, and I can only say it because of the stories that you all have shared with me. But when a client is ready for change, and we connect, magic can happen.

However, when a client didn’t ask for that kind of change, and gets the “gift” in air quotes of my services, it’s like saying “Happy I love you, now be different”.

Its happened a few times and while I only have a few horror stories, almost all of them are about clients who were given the gift of me.

Maybe I’ll share them all someday– a halloween horror story episode would be fun! This has led to me really grilling people around the holidays, and talking people OUT of hiring me as a gift.

This Linda was given the gift of me was before I started discouraging people from doing that. I got to her house, we chatted, and started going through her closet. Like most of my clients, most of what Linda had was fine.

Her things were nice, they were in good condition, and they were pretty basic. On her style questionnaire, when I asked for 3 words to describe her style, she wrote “I don’t have a style”. And honestly, she didn’t.

This isn’t to say that she had bad style, or a style that was different than mine, or clothes that were out of fashion. It’s just that everything was nondescript. No colors that stood out, no patterns, no fun shoes.

I’ve heard hundreds of women tell me “I don’t have a style”, but it’s really rare that I didn’t find one or two colors that kind of lead me down a path, or leopard print scarves instead of soft floral scarves, or a pair of stand out shoes that allude to who my client at least wants to be.

This Linda’s closet looked like it had been put together by the wardrobe department of the witness protection program.

We didn’t get rid of much. Again, everything was fine, and she didn’t have strong opinions on anything, one way or the other. I left her house a little frustrated, more with myself, because I couldn’t figure out what was going on, or how to help Linda get what she needed.

The next week, we went shopping. I loved shopping with clients because it’s a slower pace than doing closet edits. There’s the time we walk from store to store, or stand at the cash wrap, and those down moments allow for real conversation.

I was determined to crack this case, and in one store, Linda said something that gave me my first clue. A couple of the things I pulled she said “It’s a little bold”.

Now, I’m going to let you in on a little secret. Often, when working with tough clients, who I couldn’t read, I would pull the boldest, sometimes the ugliest thing I could find to try to elicit a strong reaction and force them into a feeling one way or the other.

This was not that. One was a casual tweedy boucle jacket of pinks and burgundies.

The other was a pair of Olive green pants. Neither were at all bold. So as we were walking around the mall I said “So talk to me about bold style. What does that mean to you” and she said “Anything that stands out”. I was like a-HA!

You are in the witness protection program, which of course I didn’t say. I just said “tell me more about that”, which, by the way, is the best line in the entire world. If you want to get to know someone, just say “tell me more about that” and then shut up.

You’re going to get good stuff. Here’s what Linda told me. When she was young, she had a physical challenge that affected the way she walked, and moved. And, because kids can be mean little jerks, she was teased for it.

One of the ways her mom told her to deal with it was to avoid being noticed. Not to be too loud, or to volunteer for things in class, wear things that stood out.

By the time we were working together, many years had gone by, Linda’s physical challenge had worked itself out, but for her entire life, Linda had it in her head that she should dress to avoid attention.

She didn’t buy things she loved, or anything that would stand out and be noticed. She specifically bought things to fly under the radar, undetected.

The next store we went into I said, let’s play a game. Let’s play “Do I like this” and only pick things out you really like. You don’t have to buy them, and I won’t even make you try them on. Let’s just hold them.

Now, I knew where this was going to go, and we ended up in the fitting room, trying on the things Linda loved. Turned out, she loved classic, preppy style with a lot of color and bold jewelry.

We were in the fitting room and I was fixing her sleeves, tucking things, rolling pants, like I do. I moved out of the way, and Linda saw herself.

There is this look women give when they see themselves in a mirror the way they have seen themselves in their minds, the way they have wanted to look, and it gives me goosebumps every time.

It’s not a big grin, it’s more of a little smirk, but it is so powerful. Linda gave that look, and I got goosebumps and tears.

One thing I’ve learned after watching women in fitting room mirrors for 20 years is that when a woman tries something on, her hands will immediately go to the area she’s most uncomfortable with, like she’ll pick at her midsection, or pull the fabric around her rear end down, but she will put the part she’s happiest with physically closer to the mirror.

Next time you try something on, you’ll see. Anyway, Linda took an entire step forward towards the mirror and then smiled. All she said was I love this, and I had to leave the fitting room so she didn’t see me cry.

It gutted me that she hadn’t felt that way basically her whole life. We had so much fun on that shopping trip, and then she hired me to do another shopping session, and then another closet edit where we got rid of so much stuff.

Linda was no longer in the wardrobe witness protection program, and finally had a wardrobe full of clothes that felt like her–and yes, stood out.

There are two things I want you to take away from this Linda.

First, Moms, don’t screw up your kids! Words matter, so choose yours carefully. I think we know more today about the effect of our words on our children than we did decades go, but let’s use that knowledge to keep our kids as damage free as possible.

We’re going to talk more about this in Philosophy, but things you say when your kids are little stick with them forever.

I can’t tell you all the grown women I have worked with who have issues with their bodies, or their wardrobes, or even have trouble saying “I like that sweater” because of the things their moms said to them, or the lessons they learned from their moms, when they were little.

So be very very careful with your words and actions and their long reaching effects.

The second lesson is for the women who have grown up with baggage like this. Put the emotional luggage down. Do an internal check for the BS you were told when you were growing up, and realize your mom’s intent wasn’t to damage you for life, she was just human and fallible, as we all are.

But whatever lesson you learned about how you should feel about clothes, or style, or your body doesn’t have to rule you for life. If it was a good lesson, and it helps you and serves you, by all means, hang on to that one.

But if it’s limiting and makes you feel bad about yourself, don’t wait another day to say thanks mom, but that one doesn’t work for me. And then do, and wear, what makes you feel fabulous.

We’re going to hear from one of our listeners, and then we’ll get back to the word of the week.

Karidee’s Story

I wanted to do a vocabulary word that fit with the mom theme of the episode, but it turns out there isn’t fashion word that only applies to moms, so I thought I would cover something moms love instead, and a question I get asked all the time, and that is, what is the difference between an ankle pant, a cropped pant, and a capri pant, and, most importantly, where should they hit on your leg.

Just like with the khaki/chino/twill pants discussion we had a few episodes ago, it’s important to remember that while there are actual definitions and technical differences, stores call things whatever the heck they want.

This is why is important to understand the spirit of the law, rather than the letter of the law, so you can find what works for you, no matter what it’s called.

First, let’s get cropped pants out of the way. Cropped pants are a broad category that has no actual definition of where they “Should” end.

Cropped pants are any pants that are shorter than full length pants, but longer than shorts.

They can end anywhere from your ankle to right below your knee. We’ll talk about how to find your best cropped pants in a minute.

Ankle pants are pants that end right above the ankle. There isn’t a hard and fast rule about how long ankle pans should be, but in general, they should be within a couple of inches of your ankle bone.

So many women overthink this, and really, don’t. I have ankle pants that hit the ankle bone, and some that are a few inches above it. Having your ankle pants be the perfect length is not what style is about.

I think the most important thing is to look intentional, like your pants are supposed to be a little short, especially if socks are involved in your ankle pant situation. If you need more guidance on that, head back to episode 16, all about Shoes, where I discuss this in depth.

Capri pants, on the other end, are meant to hit higher on the leg, but there’s still a big variation in what technically qualifies as a capri pant.

Capris can end anywhere the top of the calf to right below the calf–this is where you start getting into ankle pant territory. Usually, capris hit somewhere on the calf, and this is what makes them tricky.

But What you came for in this discussion is to know where your cropped pants should hit. And the answer is, that depends. It depends on the look you’re trying to achieve–ankle pants are a little dressier and more polished, capris are more relaxed and casual.

But it also depends on your legs. If you’re an Everyday Style School Subscriber, and you should be, you know that one thing I say often is “never put a horizontal line across the widest part of anything, unless you want it to look bigger” and I’m not just talking about striped tops. This is the hem of your pants, too.

So many women, especially pears and high waisted hourglasses, don’t love their legs, and so, they refuse to wear shorts, opting for cropped pants, instead.

And then, they choose a pair that ends right across the widest part of their calf, making their calves look bigger, and cutting off their legs so they also look shorter. This is not, has never been, and will never be, a winning strategy.

Every leg has a “sweet spot” where cropped pants should end for maximum flatter. For most women, it is below the calf, to somewhere right above the ankle. It is usually not right across the calf.

Now, apples and inverted triangles who are bigger on top than on bottom can benefit by making their legs look a little more substantial. How do you find that sweet spot? Trial and error.

Put on a pair of cropped pants, leave one leg long, and start rolling the other one. It’s like an eye test. Roll once–better, or worse, Roll another time, better or worse. Take pictures, so you can objectively see which is better.

Then, once you find your sweet spot, get a small tattoo right there so you won’t forget. Kidding, I’m just kidding, that’s taking style perfection a little too far! But maybe keep that picture on your phone, or measure the inseam so you can get it right every time.

The other question I get about ankle/capri/crop pants is–”Won’t they make my legs look shorter”. Yes and no Ankle pants do not make you, or your legs, look shorter.

As a matter of fact, ankle pants make you look taller. It’s a weird illusion that makes it seem like your legs are too long for your pants. So if this is a concern of yours, go for ankle.

Pants. Capris, on the other hand? Yes, will make your legs look shorter, especially if they are right across the middle of your calf. You are better off, if this is concern of yours, to go shorter, like a pedal pusher length, or longer, into ankle length territory.

I always tell my clients, we either need to see a majority of leg, or majority of pants. Half and half is the worst option, from a leg length perspective.

If your legs are long, this may not matter to you so much. If you want to make your legs look longer, this is something to consider.

I hope that clears up one of the great spring summer wardrobe mysteries, now we’re going to hear from one of our listeners, then we’ll be back with philosophy.

C. Lee’s Story:

Today, I was going to share a Naomi Wolf quote that I’ve shared before, but I actually want to share a quote from my own mom–consider this a bonus lesson from her, and in fact, it’s probably the most important one of all.

As you probably know, I was a child of the 80’s which means I wore terrible things. Horrible, hideous, awful things. One day, I was looking through pictures at my mom’s house and laughingly I said “How could you let us out of the house looking like that?”

Without a moment’s hesitation, she gave me the most profound parenting advice I’ve ever gotten. She simply said “You thought you looked great. Who was I to tell you otherwise?”

Y’all, that is good stuff. In that moment, she prepared me to be the mother of girls or at least to deal with the crazy things they wanted to wear that were not my style, but theirs.

To put aside my fears that their teachers would think I was color blind, or drank a lot in the mornings while getting them dressed.

She taught me that something doesn’t have to be my style to be good style–which has served me well in this job. But most importantly, she taught me not to be the person to burst their bubbles.

One morning, when my oldest daughter was 5, she came into my room as I was putting my makeup on in the bathroom, so I could see her in the mirror behind me.

What she was wearing made my jaw drap, and all I could say wass “WOW! Now that is an outfit”. Her little 5 year old self said “I know! Sometimes I put on things that people think wouldn’t look good together, but then I think I look amazing”.

In that moment, she thought she looked great, and if I had told her otherwise, I would have taken the wind out of her sails right then, but worse, I would have made her question herself, and not try things.

Instead, she went to school like that. And I couldn’t have cared less.

Personal style is just that–personal. It doesn’t matter if you like what your kids are wearing. If they do, celebrate it!

When I work with women who have a hard time expressing what they like, or trying new things, I often find they had moms who were controlling or critical about what they wore as kids.

Take yourself out of your kids’ style equation. It’s not about you. Yes, you are allowed to have rules and guidelines, but there needs to be some room for self expression, so they can learn to like the way they look, and feel confident about themselves.

Remember, the things we say stick with them, so make it positive

Ok, before I share a few more style lessons I’ve learned from my mom, we’re going to hear from another listener, and then I’ve got a very special announcement to make.

Courtney’s Story:

Friends, I am so excited for this. Every week, I get emails asking for referrals to local wardrobe stylists. The truth is, I don’t know that many across the country, although I do know they’re out there.

But even if I did have a list, I’d be hesitant to share it. I don’t know if that Stylist knows his or her stuff, I don’t know if they’re a good, kind person, heck, I don’t even know if they have good style!

Which is why, my friends, I am launching the Everyday Style Network next year. Qualified applicants will be able to go through the Everyday Style Certification course, where I will teach you everything you need to know to get the Everyday Style stamp of approval, and become a certified stylist.

Once you’re certified, you’re free to start, or continue your own styling business, serving clients your way, but you’ll be listed on our website so when listeners want a stylist in their area, they know they’re getting a stylist who has an eye for style, and a heart for serving women.

Certified stylists will also have ongoing support from me, and their fellow stylists. This is the training, and the support, I wish I’d had when I started out.

If you are listening to this, and thinking “I would be SO good at this” or “My daughter, sister, cousin, friend would be SO good at this” there is a form in our show notes above to get on the list for more info when it comes out..

We are in the very early planning stages right now, but we’re going to keep our first round small, so get on the list if you’re even curious.

We’re back, and ready to drop some mom wisdom on you! I’ve planned to have my mom on the show for a while, because she is so wise, and I would love for you to have heard these lessons, and more, straight from her.

But given the times we’re living in, having her over wasn’t an option, so here we are I am absolutely going to have her on the show in the future though–maybe next Mother’s Day, we’ll do Life Lessons I’ve learned from my mom, and believe me, she’s got some good ones.

But for today, we’ll stick to style.

If you’ve ever gotten a good tip from this show, or my Capsule Guides have helped make getting dressed easier and more fun, you have my mom to thank.

If you want her address to send her a card, I will happily give it to you. Because the first lesson I want to share, that I learned from my mom, is that shopping, and clothes, are fun.

You know how some families are hockey families, or soccer families, or all around sporty families? Well, our family had a sport, too, and it was shopping.

And y’all, we were good at it. My mom knew where all the sample sales were going down–you know, the kind where women fight over handbags and trample each other for deals? I saw that stuff happening before I was 10 years old.

We outlet shopped before it was fashionable–taking day trips to a small out of the way town for deals on Benneton. Her happy place is TJ Maxx. I joke that I’m going to scatter her ashes in the shoe department someday.

Over the years, clients have been impressed by my shopping stamina, but I’ve not nothing on my mom. She holds the record for marathon shopping ability.

But my favorite story is this. I have a younger sister, who was born in late December. In Minnesota. Now, for those of you who don’t know, that means it was cold.

Really cold. The day we picked my mom and newborn baby sister up from the hospital, according to google, the high was 10 degrees, -12 for my celcius listeners So yeah. Cold.

Most people would take that as a sign to take your 4 day old baby straight home, right? Not Sonja. Oh no. Upon getting in the car, she said “I need to stop at the mall”.

So, our family went to Dayton’s, which was a wonderful department store that was eventually eaten by Macy’s. I don’t remember how long we were out, or what she bought, but the take away is this–my little sister was in a mall before she was even in her home.

That’s dedication to shopping, my friends. So, when I tell you that this is in my blood, now you know I’m not kidding.

While she is more of a gatherer in her approach to shopping, I’ve grown to be a hunter, and I believe in being selective, and targeted in my approach to buying, but what she did instil was a sense that clothes should be fun, you shouldn’t be afraid of trying new things, and you should buy things that light you up.

These are principles I share everyday, and they’re foundational to Everyday Style. Now, maybe you want to go straight home after being discharged from the hospital, and that’s ok, but you can still take away to have fun with clothes and style

Let’s hear from another listener, and then I’ll share another Mom lesson

Andrea’s Story:

Lesson #2

The second lesson my mom taught me was more practical in nature, and that was the power of accessories! I bet if you asked people who know my mom about her style, they would talk about her shoes and jewelry. Especially in her working days, she was a shoe addict, and I can still picture the boxes stacked in the closet labeled taupe heels or navy loafers.

The top drawer of her dresser was an absolute treasure trove of fun accessories–especially interesting necklaces. Also, because of her shopping prowess, she finds fab accessories everywhere.

We went to lunch a few months ago and I said “I love that necklace, where did you find it?” and she told me it was from the grocery store.

I was like “I buy food at the grocery store–where the heck are you shopping??” She has a knack for finding interesting pieces everywhere, and when she finds a piece that speaks to her, she buys it.

When I think about my mom’s wardrobe, her clothes tend to be more basic, but she’s always got a great necklace, or earrings or sculptural pin to keep things interesting.

Now that I’m saying this, I realize that’s my style as well! Which brings me to lesson #3, which you’ll hear right after this lesson from a listener

Joanne’s Story:

Lesson #3 is that my mom knows how to dress herself. She has taken the time over the years to figure out what works for her, and she sticks to it. From the silhouettes she chooses to the colors she wears, she knows what looks good on her.

My mom and I are built very similarly-bigger on top, no butt, good legs, and there are certain outfit formulas she has gravitated to over the years that look remarkably like the outfit formulas I look best in.

Because we have the same build, and she knows how to dress herself, she did impart advice over the years, like “raglan sleeves look best” and look for straighter dresses without a waist, although there was never a formal masterclass in dressing the Apple body type–I don’t think she had a word for it, she just knew how to dress me, because she knew how to dress herself.

A few years ago we were shopping, and I picked up something I thought she’d like and she said “I don’t look good in black”, and at that moment, I realized that I’ve only seen her wear black rarely.

She chooses grey, navy or taupe, which yes, are better for her. She never made a fuss about “black looks terrible on me” or “I can’t wear turtlenecks”. She just wore things she knew looked good.

Now that I dress people for a living, I know for a fact that she and I share the least common body type–it can be incredibly difficult to find clothes that feel like they were made for us. And of the 12 color types, the coloring we have makes up less than 5% of the population.

It would have been very easy for her to complain that nothing looks good, or have a wardrobe full of unflattering clothes, or to have nothing at all. But she didn’t.

She’s always had a wardrobe full, quite literally, of clothes that were flattering and that she loved. I think there’s a big lesson in that, too.

This is not to say that she didn’t lament being tough to fit, because that was a refrain I heard a lot growing up, but she didn’t give up on style–and that made all the difference.

There are so many lessons I’ve learned from my mom, but today, let’s recap.

  • Have fun with style
  • Accessories are the key to a great wardrobe and finally
  • Know how to dress yourself, and focus on finding things that are great for you, rather than being discouraged by

This week for your homework, I encourage you to think about the Style Lessons you learned from your mom–both positive and negative. Send gratitude for the ones that help you, and serve you, and let go of the ones that don’t. You are now a grown woman who can decide if the things you learned from your mom are valid, or not. If you’re a mom of daughters, I also want you to think about the style lessons you want to pass down.

If your daughter was calling into a podcast 20 years from now, what would you want her to say, and how are you making that happen.

If you’re up for a little extra credit, call your mom this week and tell her about an outfit she wore when you were young that made her look beautiful. I bet that will really surprise her and make her day.

If you are no longer able to call your mom, share that memory of her with your kids, or come tell us about it in the Style Lounge. I would love to hear these stories.

And a big thank you to my own mom. Without you and these lessons, quite literally none of this would have been possible. Thanks mom.

That’s it everyone–I’ll see you Monday with office hours!

Class is dismissed for today, but the conversation doesn’t have to end. Head back up to the beginning of this post for the show notes, freebies, and a link to join my Free Facebook community, The Everyday Style Lounge.

And if the Everyday Style School podcast is helping you love getting dressed again, it would make my day if you would subscribe to the podcast, leave a review and share it with your friends, so women everywhere can have more fun with style. Thanks Style Sister.

I’ll see you next time, and until then, Stay Stylish!

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