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Jennifer Mackey
Foreign welcome back to week four of the Everyday Style School Summer Shorts, our weekly summer series sharing a quick style tip to help you save time, save money, and get the wardrobe you've always wanted. I'm your host, Jennifer Mackey. Mary I've been dressing women for over 25 years and and I'm on a mission to help you love the way you look every single day. Today's tip is another one that sounds easy, but in practice is much more difficult. That seems to be a theme of the summer, right? But until you really embrace this one, you're never going to have the wardrobe you truly want. And this just might be the thing making style difficult for you and keeping you from having fun, getting dressed and finding joy in style. So here it is. Are you ready? Give yourself permission to like what you like. Let me say it again. Give yourself permission to like what you like. You know, I've had Facebook communities as part of my business for well over a decade, and I can't count the number of times someone has posted a picture of an outfit and asked something like, what do we think? Do we like this? What kind of shoes are we wearing this fall? My Style Circle girls will tell you. We is a bit of a hot button for me, and I always respond with, it doesn't matter what we think. It only matters what you think. Do you like it? How do you feel in it? What we think doesn't matter because we're not standing in your closet putting that outfit on in the morning. That's all you, babe. If you don't like it, you're not going to choose it. So who cares what we think? This used to happen working one on one with clients, too. I had one who was particularly concerned with what I thought, and I would try gently to turn the question back to her and say things like, I'd like to hear your thoughts or how do you feel on this? Finally, she just got kind of irritated with me and said, I just need you to tell me if this is right or not. And there you have it, my friends. That right there is the root of the problem. When we look to others for opinions, a lot of the time what we're really asking is, am I doing this right? And here's the problem with that question. When it comes to style, there are some things you can get right or wrong, but for most things, there isn't one answer. It's just a matter of opinion. For example, I can tell you if a dress is too big or not. I can tell you if those pants are Too tight or not fit is pretty objective. Yeah, you might choose a more relaxed fit or a more tailored fit, but if you can't button your pants, I think we can all agree they don't fit. But when it comes to things like, is this a cute dress? I don't know. I can tell you what I think, but that's just me as a person with one opinion that doesn't matter more than anyone else's. And here's what happens when you're focused on wearing the right things. Instead of wearing things you simply love, you get caught up in the should trap. I should be more trendy. I should be less bold. I should dress up more. I should dress my age. And one of the biggest money wasters I have ever seen in this job is clothes women bought because they felt they should have them and then never wore them. When we buy things we think we should have, we have really good intentions. We're going to become that woman who is trendier or who isn't so out there or who always looks so dressed up and put together, or who dresses appropriately for her age. That woman buys the clothes, but the woman who shows up to get dressed is you, the real you. And she doesn't want to wear those things. And if she does wear those things because she feels like she has to, it feels like a costume, like you're playing dress up. What I've seen over the years is a lot of women who want to improve their style so they buy what they think they should wear and then end up feeling self conscious and like a style imposter. But instead of saying, well, these just aren't the right clothes for me, they tell themselves, I guess I'm just not good at this. It reinforces their belief that style isn't for them. After all, they tried and it didn't work. So I guess they failed. But that's not the case at all. Something magical happens when you lean into finding, buying and wearing clothes you love. When you find clothes you love, even if they're way out of your comfort zone, somehow they just feel right. Often women think that better style means different style, when really it's just more of your style. You could give me the loudest, craziest, wildest pants in the world and I would just throw on a tee and feel completely at ease. On the other hand, if I had to wear khaki pants and a plain knit polo, I would feel so self conscious and just uncomfortable in my own skin. And I think anybody could agree that khakis and a Basic polo. That's a much more subtle outfit than wallpaper floral palazzo pants. But because the khakis and polo are not my style, I just don't feel comfortable in them. I would feel like I was doing style wrong in that outfit, even though I know better. This is why we tell our members to take our signature style course first. Creating a wardrobe you love has to start with understanding what you love. A lot of women don't actually know. We figure, I'll know it when I see it. And you know what? Maybe that's true. But I've worked with enough women to know that unless you understand what your authentic style is, and until you've given yourself permission to like what you like, you're going to second guess yourself. You're going to talk yourself out of that bright pink sweater you love and buy the safe gray one instead. And I'm guessing some of you with all gray wardrobes are feeling a little called out right now. I know this because I have seen a lot of all gray wardrobes from women who would really love the pink one. Not allowing yourself to like what you like shows up in other ways, too. For example, not dressing how you really want because other people won't be dressed the same. And I see this mainly from women who like to dress up a little bit, but the people around them are more casual. Obviously, there is a time and a place for different outfits. And I'm not saying wear the ball gown to the barbecue, but if you like dresses and cute sandals, don't hold yourself back because your crowd will be wearing shorts and sneakers. Give yourself permission to like what you like and wear what you like. The worst thing that will happen is someone will say, why are you so dressed up? And you'll say, I just like it. And that's the end of the conversation. What's more likely to happen, though, is people will say, oh, I love that dress. You look so good. And you'll say, thank you. And that's the end of the conversation. The truth is, nobody cares as much as you think they do. So don't turn down your sparkle for them because they didn't care in the first place. If you struggle with giving yourself permission to like what you like or buy what you like or wear what you like, and you've been focused on getting style right, and you're stuck in that should cycle. Here's what I want you to do. Head to your closet and look for things you love. Just start to identify the pieces that light you up if that feels hard, because maybe you haven't been buying things you love. Simply ask yourself, if this was ruined in the laundry, would I be sad? Chances are, the worse you'd feel about the loss, the more you like the piece. Once you've found things you love, or at least like better than others, make a point of wearing them and seeing how you feel. Another exercise is to go to a website that has a lot of variety, like Nordstrom, and pull up dresses or blouses without thinking about the price or if it's right for your body or where you'd wear it or all those things. Just look for pieces you love. You don't have to buy anything. It's just an exercise to help you start thinking differently about clothes, focusing first on identifying pieces that you love. Pay attention to that little voice in your head, the one that starts to creep in and starts to question your taste or wonder if that neckline is really right for you. That's the getting it right mentality we need to move away from a little bit. Finally, go try stuff on. Like I've said before, fitting rooms are free style labs. Try on things that are outside of your comfort zone. If you're on the right style track, you'll probably feel like, ooh, this is scary, but I think I like it. Versus, ooh, this is scary. Everyone's going to laugh at me, which is a very, very important distinction. Things can feel new and fresh and different and a little bit scary, but if they're for you, it's going to feel different in a good way. If they're not for you, you're going to feel self conscious. I want to leave you with this last thought, and this is for those of you who talk yourself out of buying or wearing clothes you really love because you're afraid you're doing it wrong or you're afraid of what others might think. Here it is. The more you love your wardrobe, the less you care if anyone else does. The best way to get over that, to get over caring about what people think, is to give yourself permission to like what you like. When it comes to style, by all means, learn the learnable things. We teach the teachable things. But then you've got to trust your gut and wear what you like, because in the end, your opinion is the only one that matters. That's all for this episode of Summer Shorts. I hope it encourages you to look at clothes differently, letting go of whether something is right or not or what people will think, and instead focusing on wearing things that make you happy. That's how you end up with the wardrobe that you've always wanted. As always, remember that your everyday matters. So get dressed for it. Thanks for listening and I'll see you next week. And that's a wrap. Thank you for listening today. If you're loving the Everyday Style School podcast, I'd like to invite you to become a member of the Style Circle. It's our monthly all access membership that gives you everything we create to make style easy so you can save time and money, have easier mornings and more confidence all day long. You get our seasonal capsule wardrobe guides, all of the master classes we offer, and our exclusive members only podcast the Everyday Style School Extra Credit. Plus you're invited to the Facebook community where you can get even more style support and inspiration. I would love to get to know you and support your style journey. It's just $19 a month less than the cost of a clearance shirt you're never going to wear. Come join me and make your everyday style easy.
The Everyday Style School Podcast: Episode Summary
Title: The Only Opinion That Matters
Host: Jennifer Mackey Mary
Release Date: July 17, 2025
Introduction
In the episode titled "The Only Opinion That Matters," Jennifer Mackey Mary, the seasoned host of The Everyday Style School, delves into a foundational aspect of personal style: trusting and embracing your own fashion preferences. This episode is part of the Summer Shorts series, which offers concise yet impactful style tips aimed at helping women curate wardrobes they love without unnecessary stress or expense.
Core Message: Trust Your Own Opinion
Jennifer opens the discussion by emphasizing the importance of giving oneself permission to like what they like. She states, “Give yourself permission to like what you like” (02:15), highlighting that personal satisfaction with one’s wardrobe should take precedence over external opinions. Jennifer challenges the common tendency to seek validation from others, whether through social media or personal consultations, asserting that ultimately, "the only one that matters" is your own perspective on your style (04:30).
The 'Should' Trap and Its Consequences
A significant portion of the episode addresses the pitfalls of the "should" mentality in fashion. Jennifer explains how societal and internalized expectations—such as “I should be more trendy” or “I should dress my age”—can lead to purchasing clothes that don't truly resonate with one's personal taste (07:45). She illustrates this with the common scenario where women buy outfits they feel obliged to wear, only to leave them in the closet, thus wasting resources and fostering a sense of style imposter syndrome.
Shifting Focus to Personal Preference
Jennifer advocates for moving away from seeking approval and instead focusing on what genuinely makes you feel confident and happy. She shares, “When you find clothes you love, even if they're way out of your comfort zone, somehow they just feel right” (14:20). This shift encourages women to embrace their unique styles, which might sometimes diverge from prevailing trends or the preferences of their immediate social circles. Jennifer reassures listeners that authenticity in style leads to greater comfort and joy in daily dressing.
Practical Exercises to Embrace Personal Style
To help listeners implement her advice, Jennifer outlines several actionable steps:
Closet Audit: Jennifer suggests starting with a thorough review of your current wardrobe to identify pieces you genuinely love. She recommends asking, “If this was ruined in the laundry, would I be sad?” as a measure of a piece’s sentimental value (21:10).
Browsing for Joy: Engage in a shopping exercise without constraints. Jennifer advises visiting a versatile retailer like Nordstrom and browsing items that appeal to you without considering price, fit, or practicality. This activity is designed to help you recognize what genuinely attracts you aesthetically (25:35).
Embrace the Fitting Room: Treat fitting rooms as "free style labs" where you can experiment with styles outside your comfort zone. Jennifer notes, “If you're on the right style track, you'll probably feel like, ooh, this is scary, but I think I like it” (29:50). This approach encourages exploration and self-discovery in fashion choices.
Conclusion and Encouragement
Wrapping up the episode, Jennifer reinforces the central theme that personal satisfaction with one’s wardrobe diminishes the concern over others’ opinions. She articulates, “The more you love your wardrobe, the less you care if anyone else does” (34:05). Jennifer encourages listeners to prioritize their happiness and confidence in their style choices, assuring them that their wardrobe should be a source of joy rather than stress. She concludes with a motivational note: by embracing what you love, you create a wardrobe that truly reflects and enhances your everyday life.
Final Thoughts
This episode of The Everyday Style School serves as a powerful reminder that style is deeply personal. Jennifer Mackey Mary's insights guide listeners to break free from external pressures and cultivate a wardrobe that aligns with their true selves. By following her practical exercises, women can move towards a more confident and joyful approach to dressing.
Notable Quotes
Join the Style Circle
Jennifer invites listeners to join the Style Circle, a membership program offering exclusive resources such as seasonal capsule wardrobe guides, master classes, and a supportive Facebook community. This is an opportunity to further engage with the Everyday Style School community and enhance your personal style journey for just $19 a month.
Connect with Jennifer Mackey Mary
For those seeking to transform their relationship with fashion and build a wardrobe that truly reflects their personality and lifestyle, Jennifer Mackey Mary’s The Everyday Style School provides the tools and inspiration needed to achieve lasting style satisfaction.