Jennifer Mackey-Mary: Hello Gorgeous! 

Welcome back to week 4 of The Everyday Style School: Summer Shorts–our weekly summer series sharing a quick style tip to help you save money, save time, and get the wardrobe you’ve always wanted.

I’m your host, Jennifer Mackey-Mary. I’ve been dressing women for 25 years, 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. But until you really embrace this one, you’ll never 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–you ready? give yourself permission to like what you like. Let me say it again–give yourself permission to like what you like. 

I’ve had facebook communities as part of my business for over a decade, and I can’t count the number of times someone has posted a picture of an outfit, and asked “what do WE think?” “Do WE like this?” My style circle girls will tell you WE is a bit of a hot button for me, and I always respond it doesn’t matter what WE think…it only matters what YOU think. Do YOU like it? What we think doesn’t matter, because we’re not standing in your closet putting that outfit on. 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 on on one with clients, too. I had one who was particularly concerned with what I thought, and I tried gently to turn the question back to her, and say things like “I’d like to hear your thoughts”…and finally she got irritated with me and said “I need you to tell me if this is right or not”...and there you have it friends. That right there is the root of the problem. 

When we look to others, even me, for opinions, a lot of the time what we’re really asking is “Am I doing this right?” Here’s the problem with that question. When it comes to style, there are are some things you can get right or wrong, but for most things, there isn’t one answer. Its a matter of opinion.  For example, I can tell you if a dress is too big or not. Fit is pretty objective. Yes, you may 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 right? 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 elses.

Here’s what happens when you’re focused on wearing the “right” things instead of wearing things you simply love. You get caught 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’ve ever seen in this job is clothes women felt they should have.

When we buy things we think we SHOULD have, we have 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 it feels like a costume. Like she’s 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, then end up feeling self-conscious and like a style imposter, but instead of saying “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, they tried, it didn’t work, so therefore they failed. When that’s just 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, they feel right. Often women think better style means different style…when really it’s just more of your style.

You could give me the loudest, wildest, craziest pants in the world, and I would throw on a basic 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. I think we could all agree that khakis and a basic polo are more subtle than wallpaper floral palazzo pants, right? But because they’re not MY style, I 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 the 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–I’ve seen lots of all gray wardrobes.

Not allowing yourself to like what you like shows up in other ways as well. For example, not dressing how you really want because other people won’t be dressed the same. I see this mainly from women who like to dress up a little more, but the people around them are more casual. Obviously, there’s a time and a place for different outfits, and I’m not saying wear the ballgown to the barbeque…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 that 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 stuck in the should cycle, here’s what i want you to do. Head to your closet and look for the things you love. Just start to identify the pieces that light you up. If that feels hard, 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 the things you love, or at least like better, 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, 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 things you love. Pay attention to the voice in your head–do you start to question your taste, or wonder whether that neckline is best 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 like, "This is scary, but I think I like it" versus "This is scary…will everyone laugh at me?" A very important distinction.

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–the more you love your wardrobe, the less you care if anyone else does. The best way to get over that is to give yourself permission to like what you like. 
When it comes to style, By all means, learn the learnable things…but then 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, and instead focusing on wearing things that make you happy. That’s how you end up with the wardrobe 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.

Jennifer Mackey-Mary [outro]: 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 masterclasses 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 gonna wear. Come join me and make your everyday style easier.