Jennifer Mackey-Mary: What if the same habits you do every day–at work, at home, in your relationships, could also make your style better? Chances are, you’re already doing at least some of what we’re talking about today without even thinking about it, but when you apply these 4 habits to shopping and getting dressed, they can have big results. I’m a fan of working smarter, not harder, so today, we’re talking about how to intentionally use the things you’re already doing to improve your style. Let’s get started. 

Welcome to the Everyday Style School, the show that teaches you everything your mom never did about getting dressed.  I'm your host, Jennifer Mackey Mary. After 25 years of dressing women with real bodies, real budgets, and real lives, I know great style isn't about following one-size-fits-all advice - it's about learning what works for you.

Hello Gorgeous! 

Another Spring Season episode, another conversation about habits. But this time, we’re not talking about the habit of dressing well, which hopefully you’ve been practicing, and we’re not talking about things like planning your outfits for a week, adding an accessory, or turning your hangers around so you know what you wore that year. Those are style-related habits, and yes, good style habits are important, but outside of our closets, there are so many things we do, on autopilot, that can be used to make style easier and better–if we use them intentionally.

I made a bold claim in the opening, that you’re probably doing most of these things already, and if you are, great! But, some of these life habits might not be things you practice regularly, and if that’s the case, well, you just got a free side of life coaching with your style advice. You’re welcome. 

Let’s just get to it, shall we?

The first non-style habit that will improve your style is:

Loving solutions more than you love problems. I know it sounds crazy, like who loves problems, right? But as a lifelong advice giver, I can tell you, a lot of people do. A lot of people LOVE their problems and seek to protect them at all costs. Let me explain what I mean. Over the years, I’ve given a ton of advice, and helped people work through all kinds of problems. Style problems, obviously, but I’ve been in group coaching programs for my business, talked about relationships or parenting with friends, you know–just what you do. And here’s what I’ve noticed. There are two scenarios. One is that someone really wants a solution, and they’re willing to listen, and try things to solve the problem–not necessarily take advice blindly, without thinking it through, but there’s an openness.

The other scenario is people who present their problem as though they want to fix it, but they really don’t. It becomes clear real quick that they’re not ready to let go of it, or try anything new to solve it. Every suggestion is met with resistance. I call these people “Yeah, buts” and I can’t wait to see what the auto transcription does with the word “Yeah, but”, but here’s how it goes. Let’s say a friend tells me “I need to exercise more, but I just don’t know how to fit it in my day”. I might say “could you go to the gym in the mornings”, “Yeah, but I go to bed late, and it’s tough to get up earlier. Girl, I get it.. what about going to bed 30 minutes earlier? Yeah, but that’s my only time to decompress by myself. Ok, what about lunch time. You work from home, so you could just take a break “Yeah, but I get dressed in the morning, and don’t want to change at lunch”. Could you wear a nice athleisure outfit a couple of days a week so you don’t have to change” “Yeah but I don’t want to buy more clothes just so I can work out”... you see where I’m going. No matter what solution they’re offered, it’s probably going to be met with “yeah, but”, which to me, is the sign that someone isn’t ready to let go of the problem, and at that point, I stop trying to help because it’s just wasting my breath and energy.

That’s not to say that you have to love, or follow, every solution someone proposes, because let’s be honest, some advice just sucks. I remember years ago, in the early weeks of Covid, I was in this group program for women business owners, and we were having a discussion about changing our models and products to meet our customers where they were at–which was a good conversation to have at that moment. One of the women told me “I have a great idea–you should design dog collars and leashes because everyone is walking their dogs a lot more” I could have yeah, butted that idea for days, because it just wasn’t good advice. I don’t design or manufacture anything. I don’t work with pets. All I said was “yeah, that’s an interesting idea thanks”. And moved on. Point being, just because you got advice, doesn’t mean you have to take it. 

But when you’re shutting down every good, practical, realistic solution, from someone you consider to be a fairly wise or smart person, it’s a good sign something else is going on, and it’s usually one of two things.

First, you’re looking for ONE perfect solution and you don’t want to change anything you’re doing to get it. You’ll only trade your problem for a solution that is easy, comfortable and solves everything. The problem is, that solution usually doesn’t exist. If it did, you’d already be doing it. 

I hear from a lot of women who have tricky feet, and their problem is that they can’t find cute shoes. I struggle with the same thing, so I get it. But often they don’t want to try different brands, or order a bunch online, pull out the standard insoles and add their own, spend more money–you name it, there’s a yeah, but answer for every suggestion. What they want is cute shoes that look like everyone else’s that work for their specific feet without any customization or ordering 20 pairs from zappos to find 2 that work, oh… and they don’t want to pay a lot for those magical shoes. 

Again, I get that desire, but that solution simply doesn’t exist. And often, when faced with the lack of one singular perfect solution, we convince ourselves that the problem ISN’T solvable, when really, it’s just not perfectly, easily solvable in a way that requires no effort or change–and that’s not the same thing.

The other reason for yeahbutting goes deeper, and it’s that your problem is protecting you from something. It’s keeping you safe. I’ll use myself as an example. Many years ago, when I started my business, I got invited to do a speaking engagement that was way outside of my comfort zone, and I was excited for it, but I literally had nothing to wear. Remember I started this when my baby was a year old, meaning my body and wardrobe were in that postpartum flux, and I was not feeling great about myself. I went to Nordstrom for help, and the woman, looking back, brought me some wonderful things. But I yeahbutted on that woman so hard. A sweater “yeah, but that it’s too fitted”, a dress “Yeah, but that print’s a little busy”, A pretty blouse “yeah, but that neckline isn’t right”. I was unwilling to even try anything on, because deep down, I was uncomfortable being seen. I didn’t want anything that showed my shape, or drew attention to me. I was perfectly capable of helping others one on one but I was uncomfortable being on display. If that sweet woman who by the way if you’re listening 14 years later, I am so sorry, if she had brought me an oversized trash bag that covered me from neck to toe, I probably would have been like “yes, that’s amazing, exactly what I was looking for”. Solving the problem made me feel too vulnerable, so I found fault with all of the solutions. 

The first step to loving solutions more than you love the problem, whether it’s for your style, or your life in general, is to train yourself to be aware of when you’re yeahbutting. Just listen for it. I caught myself doing it a couple of weeks ago–it happens. But when you catch yourself doing it, ask yourself “what would the perfect solution be” “what am I looking for in this moment”? You might quickly realize that you’re looking for a one-and-done solution that doesn’t exist. Or you might realize there’s no solution that will solve the problem, because the problem goes deeper than the proposed solutions. 

Then ask yourself this question–and it’s my favorite question in the world–what ARE you willing to do? That’s it, what are you willing to do. If you’re not willing to try 20 pairs of shoes from zappos, or spend $200 on the perfect pair of shoes, fine, great–but what ARE You willing to do? The truth is, any problem can only be solved to the degree of what you’re willing to do. If you’re not willing to spend extra money on the right shoes, or extra time looking for brands that work, or extra energy ordering and returning, the problem probably won’t be solved. In that Nordstrom fitting room, I would have been willing to put on something less body conscious, less bold. Something that felt closer to what I was comfortable in–and if I had had those words that day, I probably would have had a better result. But I didn’t. I just got defensive and convinced myself that it was either to feel self-conscious and exposed on stage, or nothing. But there’s always something you can do, if you’re willing to be open, and get to what the real problem is.

When people are giving you advice, and solutions, they’re not going to all be perfect for you, but instead of focusing on why they can’t work, look for what you can take from them. Even the ridiculous suggestion of dog collars had some merit–she’s right, people were walking their dogs more, so I did some social posts about sneakers, and dog walking outfits. In that fitting room, instead of shutting down blouses completely, I could have said, “I feel good in blouses, but I like a higher neckline”. That’s loving a solution more than loving a problem, and it’s the only way to truly make progress.

The second non style habit that will actually improve your style is…

Be curious. If you notice, the first step to stopping the yeahbut cycle was simply to notice yourself doing it, right? But the next steps were all about asking yourself questions…what would the perfect solution be, what am I looking for right now, and what am I willing to do?  Those are all part of being curious. 

I think curiosity is one the most important life skills, life habits, whatever you want to call it that there is. Curiosity is linked to increased intelligence and success, improved relationships and emotional intelligence, higher creativity and resilience–I could go on and on. But what I want to talk about is what happens when we stop being curious.

Studies show that natural, raw curiosity starts to really decline in our mid 20’s, and unless you cultivate the habit of being curious for life, here’s what happens:

Your thinking hardens and becomes less flexible. 

You become more defensive

You lose creative energy

Problems feel heavier

You stop evolving

Hopefully, with that list, you’re seeing the connection between the importance of curiosity and style, right? When your thinking is less flexible, instead of saying “huh, that’s interesting” when you see a new trend, you automatically think “that’s stupid. Who would wear that”. Instead of saying “oh, this rise isn’t the best for me”, you get defensive and say “I have a weird body. Nothing works for me”. Those problems we talked about in habit #1 feel unsolvable. You stop trying new things, and eventually find yourself in a style rut with a dated wardrobe.

Curiosity is so important when it comes to style, and one of the best ways to use it is when you try something that doesn’t work. Most women try something on in a store, or put an outfit together at home, and if it doesn’t look right, they go “nope, not for me” and that’s the end of it. 

Curiosity though, would say “WHY doesn’t this work” “what don’t I like about this” “what would need to change to make this successful?” In the first scenario, you gain nothing. You have no more information to help you make the next decision. It’s just all trial and error and starting from scratch. But when you get curious, and you say “I don’t like the way my legs look in this dress” or “I feel boxy in this outfit” --even if you don’t know how to solve it, you’re bringing awareness to what the issue is. I think a lot of women don’t ask those questions, because they don’t have the solution, but if you find yourself saying “I feel boxy in this outfit” over and over, you discover a pattern. You can even google “how not to look boxy in clothes”. Solutions are easier when you know what the problem is, but if you never get curious about it, you just assume it’s you. 

It works the other way, too. When you find a piece you love, or an outfit that makes you feel like a million bucks, ask yourself “WHY?” what’s working well, what’s different about this particular piece or outfit than other similar things that don’t make me feel this good? Last season, I did an episode on personal style fundamentals, and one of them is knowing your must haves. You can’t know that unless you get curious about why you love the things you love. I mean, I guess your must haves can simply be the swatches on a color card, or the necklines you’re supposed to wear for your body shape, but those are poor substitutes for knowing what YOU love. You, not everyone with the same coloring, or bodyshape. You. When you know why you like what you like, you can recreate it. When you know why you don’t like what you don’t like, you can avoid it. But you only discover those things when you get curious. 

The third non-style habit you can use to improve your style is: Consume information intentionally. Do you ever think about how much information, or how much content we consume every day? It’s crazy. It’s coming at us all the time. You’re doing it right now. Heck, I put gas in my car the other day, and the pump wouldn’t start until a commercial on the screen played. We can’t avoid it. We consume so much information that most of it just goes in one ear and out the other. And it’s not because we’re dumb–it’s because we’re overwhelmed with information. 

And passively consuming information is fine for some things. I don’t remember what the gas pump commercial was for. I listen to music mindlessly, and even some podcasts. I scroll Instagram reels or TikTok for entertainment. I’m not trying to get something out of them, so it’s not a big deal. But the problem is when we consume all information that way, we miss a lot of stuff, and unfortunately, I think skimming the surface has become our default setting most of the time, unless we’re aware of it. 

There’s a meme that cracks me up every time I see it, and it’s a Facebook post about a woman selling pies, and she says I have apple, cherry, and blueberry. They’re $10 each, and I accept cash and Venmo. You can pick them up on Thursday after 5pm. And the comments are: What kinds of pies do you have. How much are your pies. Do you accept credit cards. Do you deliver? What day are they available?  

If you’ve ever been in a position where you’ve had to communicate anything to anyone, you know why this is so funny to me. It’s like, the information is all right there. Pie lady did a good job of communicating, but our skimming brains just gloss over all of it. I find myself being guilty of this too, and I’m trying to slow down, and before I ask a question, I reread the post or the email to see if the answer is actually right there, and often, it is. That’s the difference between mindlessly consuming information and consuming it intentionally. When you consume with intention, you’re way more likely to get what you need out of it. 

There are a lot of ways to apply this habit to your style, so let’s talk about a few.

The first one is to consume information through the lens of what you’re trying to get out of it. For example, and this is something I talk about all the time. Read online clothing reviews like a detective, looking for clues that help YOU to know if something is right for you. If I look at a pair of pants, and it has nothing but 5-star reviews I might go, great, perfect, that’s a winner. But if I read the reviews, and they say things like “first pants that don’t give me the gap in the back” or “great for my curvy hips”, those aren’t 5-star pants for me. I need the reviews to say “these gave me the biggest gap in the back ever”. If you tend to run hot, do the reviews of a sweater all say this kept me so cozy even during the coldest winter days? If they do, it’s not for you. 

Another way is to seek out information that will help you, instead of just consuming whatever you’re offered. Let’s take scrolling social media. You probably follow some style influencers, right? But have you actively sought out influencers who are your age, have your shape, or have your lifestyle, or your ideal style? That woman who travels all the time and goes to fancy restaurants every week might have some great outfits, but if your life doesn’t look anything like that, does it really help you? Every now and then I’ll have people say something like “everyone’s wearing such and such and it’s not in the capsule” and I’ll be like? Really, I’m not seeing that, so I ask them who are you following, where are you seeing this? And it will be like “Oh, my college daughter and her friends”. Yeah, so that’s not a trend I missed, it’s a trend that doesn’t apply to my women. I’m looking for things that apply to the women I serve, which is how we help women look current without feeling like they’re trying too hard. I’m seeking out specific information, not just treating it all the same. 

The last way to use this is to train yourself to look for nuggets–and this really applies to long-form content, like a podcast, YouTube video or a course. Getting information from the internet can feel like drinking water from a fire hydrant. You’re thirsty and just want a little drink, but you end up being waterboarded instead. It’s overwhelming, and can leave you feeling worse off than you were before. Something I do when I go to a conference, or listen to a podcast, whatever….is to train myself to listen for nuggets. And what I mean by that is that when I listen to a podcast about mindset, or business, or finance, I don’t expect myself to retain all of it. I just tell myself to find 3 nuggets of wisdom, or takeaways, or ideas that I’ll actually do–whatever you want to call them. I call them nuggets. Just find three.  What this does is first, it reduces the overwhelm. It lets you off the hook and you don’t have to feel like you have to do everything that expert says. Nope, just find 3 nuggets that can help you. That seems a whole lot more doable, right? The other thing it does is that it sharpens your listening. When you go into something intending to consume all of it equally, your mind tends to drift, and you start to listen passively, and you end up getting nothing. However, when you say, I’m just looking for 3 nuggets of wisdom, you sharpen your listening, and you end up getting more than 3 nuggets because you were tuned in. Think about how many podcasts, how many YouTube videos, if you’re a style circle member, how many classes you could consume in a week, or even a day. You’d end up with way more ideas than you could ever realistically do right? It all just becomes nice ideas that don’t go anywhere, and when that happens, you feel defeated, and like nothing works. But when you set a goal to find 3, or heck, even 1 thing you could and will actually do, you’re going to make progress. Do you notice that when I give you homework, I tell you to pick one or two things? That’s intentional. Idea overwhelm and big plans don’t do anything for you. Small actions do. But in this day and age, you have to filter the tsunami of information coming at you all the time to choose the actions that will help you most. 

The last non-style habit that will actually improve your style is giving compliments. 

I love giving compliments. I really do. I think as humans this is one of the kindest gifts we can give to people, and it’s free, so I try to be generous with compliments–and you never know how much your words might mean to someone. I was in target when my youngest was a toddler, and I was getting her an icee in the snack bar, because I am a lazy, bad mother who just wanted to buy cleaning supplies in peace. Don’t judge me. Anyway, there was a woman sitting in there with this red suit on, complete with a big, dramatic church hat and heels. She certainly stood out on a weekday morning in a suburban target. I walked over to her and said “You look fabulous–red is definitely your color” and she started to cry, and said there was no way I could know how much she needed that. She told me she’d lost almost everything in a house fire, and she was tired of wearing clothes that people gave her, she wanted to have her things back, so she bought one outfit that made her happy. And I think that’s a real testament to the power of clothes, what they mean to us, and what they can do for us, which is what I really love about clothes. But is also a testament to the power of kind words. You never know who needs to hear something nice, so give nice words to everyone. 

And you’re probably like, cool story Jen, but how does that help me improve my style? Great question, let me tell you. When you make a habit of complementing people, what you’re also doing is training your eyes to notice things. One of the best ways to improve your style is to people watch–I’ve said that a million times. But when you’re on a mission to give compliments, you dial it in even more and actively, intentionally look for things, and that’s where you start to find real life inspo. 

To make giving compliments super effective as a style-boosting strategy, your compliment needs two things. First, it must be genuine. Let’s be honest, the target woman’s outfit was not my style. I am not dressy and dramatic and over the top. So, I didn’t say, I love your outfit, where did you get it? But you don’t need to want someone’s style to recognize that they look fabulous, and red really was stunning on her, so that’s what I told her. Sometimes, you’re going to see things you like, and that’s great, but you’ll also start to recognize good style that isn’t yours, and that’s important, too. One of the things I love to hear our members say is that now they can recognize pieces or outfits they love, but that aren’t their style. That’s actually really insightful. 

It means your own sense of style is getting clearer. So, when you’re giving compliments, remember that you don’t have to love something, or want to wear it, to recognize what’s working. That’s the part that makes giving compliments go from being a nice thing to do, to a nice thing that helps you, too. Insincere compliments don’t teach you anything. 

The second requirement for a good compliment is that it needs to be specific. “Red is stunning on you” is a better compliment than “you look pretty”. And, bonus, it trains you to notice colors on people, which sharpens your color skills. “I love how you mixed patterns in your outfit” is better than “I like your outfit”, and it gives you ideas on how to mix patterns. Specific compliments mean you’re really looking and noticing things–and that’s how you learn. “I like your top” doesn’t require anything on your part. “That neckline looks great on you–it really highlights your shoulders” requires you to see what necklines do, which is a very good thing to know. 

One thing worth mentioning here is that we don’t do insults disguised as compliments, right? Because we’re not jerks? Saying Wow, that dress looks great on you–the print really minimizes your tummy might be genuine and specific, but it’s not very kind. It’s not going to make someone’s day, so don’t do that. You can just say, wow, that dress looks amazing on you, I love the print–even if you notice the tummy minimizing effects. Just keep that part to yourself. 

I think about giving compliments this way–you know when elementary school teachers will say to the kids “turn your listening ears on”? Giving compliments is like turning your seeing eyes on, and once you do, you’ll notice all kinds of things, and find style lessons and inspiration in places you never thought of–like the grocery store, or out on a walk. There’s a lot to be learned from the people around you, you just have to notice it–and you get to make people happy in the meantime. 

That sounds like a win-win to me. 

Before we get to the homework, let’s quickly recap. Here’s what I want you to take away from this episode:

Improving your style doesn’t have to mean learning new things and creating new habits all the time. There are lots of habits you’re hopefully already doing that can be applied to your style as well. Including

1-Love solutions more than you love problems–or, as I like to stay, stop being a yeahbut

2-Be curious–channel your inner 4-year-old and ask “why” 

3-Consume information intentionally–the information age is great, but unless you’re intentional, you can end up overwhelmed and no better off.

Finally

4-Give compliments–specific genuine compliments. Not only will you make the world a better place, you’ll hone your style skills in the process. 

For the homework, normally I tell you to pick what you want to do, but this time I’m going to let you pick one, and I’ll pick the other. The one I want you to do is to give genuine, specific style-related compliments. Challenge yourself to give one a day. See how many people you can make smile this week. The other one is up to you-do whatever you think will help you most. If you feel like you’re struggling with style, practice not being a yeahbut-ask someone for advice, and just take it in. You don’t have to follow the advice, just practice not yeahbutting. If you feel like every outfit, or every purchase is a shot in the dark, practice the habit of curiosity. Every day, when you get dressed, ask yourself what’s working, what’s not working, what would make this outfit better. Finally, if you find yourself consuming a lot of information, but you don’t feel like it’s really doing anything for you, practice intentionality–look for influencers who are your age, or shape. Read reviews before you buy things, and find the nuggets when you’re watching or listening to things. 

Over time, you’ll find these simple habits add up to a big effect on your style. 

That’s it for this episode of the Everyday Style School. Thank you for spending time with me today. If you’re ready for easier, better style, come take my free workshop Style Made Simple, where you’ll discover why style has felt so hard–and how to make it easy for life. You can sign up at freestyleclass.com, or through the link in the shownotes.

I’ll see you next time–and until then, stay stylish!