Jennifer Mackey-Mary: Are you like the countless women I’ve worked with who describe their style as “simple”? In theory, this means you don’t love a ton of patterns or layers, or accessories–you just want, easy, understated pieces that come together to make polished, unfussy outfits. But the reality doesn’t always tell that story. Often, you look in the mirror and feel Boring. Blah. Bland. 

You feel like you have to wear brighter colors to bolder patterns in order to be stylish, but they just doesn’t feel like YOU—and you think maybe you have to choose between being unstylish in the pieces you like,, OR being stylish in the bold things you don’t. If I just described you, you’re in luck, because today, I’m going to show you that you can have it all. 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! It’s time to talk about making real-life, everyday style easier because that’s what we’re doing this semester., but before we do, I want to share an email I got after the Style Made Simple workshop–that’s our free class that explains exactly why style has felt so hard, and how to make it easier.  This is from Jodi who wrote “Thank you so much for the workshop. I really enjoyed it, and I feel like something finally clicked, even though I’ve been listening to you for years.  I told my husband that now I understand why I’ve spent so much money on clothes I don’t wear, and what I need to do different. I think he might like you even more than I do now!!” and then there were a ton of laughing emojis. Jodi, thank you for this email–it absolutely made my day, and thank you to Mr Jodi as well. If you haven’t taken the class yet, sign up–the link is in the shownotes. Who knows what breakthroughs you have.

But let’s get to today’s topic. Simple style. And really how to have simple style in a way that still looks, well, stylish. Not like you’re just wearing clothes. I know you know the difference. 

What I’ve encountered over the years is that women want this understated, effortless look that still looks polished and intentional–like Jennifer Anniston in a t-shirt and jeans–and again I know you know what I’m talking about. 

But in reality, that simple jeans and a t-shirt look doesn’t always come together in the mirror quite the same as it does in our minds. It just reads boring. Underwhelming instead of understated. And before you say “it’s because she’s skinny”, yes, having a celebrity body probably helps, but it’s not the only thing. I can find a million pictures of real women looking polished wearing basics. She’s just the most universally referenced person for what we’re talking about I can think of, so don’t email me about body positivity. 

Over the years I’ve worked with so many women who came to me because they wanted a simple style, but they also wanted to feel more put together. They didn’t like a ton of pattern, or lots of accessories, or in some cases, even color. And before we worked together, when they were feeling flat instead of fabulous, their usual approach was to go buy clothes that looked like they’d shake things up. Bold prints and colors, embellishments, whatever–they were trying to give their wardrobes a jolt of style, but, because those pieces weren’t “them”, they didn’t reach for those things, and if they did, they felt ridiculous. It felt like wearing a costume. 

I remember one client I worked with who had what I would consider to be the driest job on the planet. I honestly don’t remember what it was, but I do remember when she talked about it, I thought, there really is something out there for everyone, because I would go crazy if I had to do that day in and day out but it was interesting to her…so great. Better her than me. But her style, and even her personality went with this job perfectly. Not to say she was the driest person on the planet-she wasn’t. She was perfectly pleasant, but early on, I caught on that she did not like humor, or chit-chat or talking about herself–you get the idea. Anyway, her closet was full of black and gray suits, that were all pretty much indistinguishable from each other. Her wardrobe was as basic as it got. Except for this little section of her closet that was dedicated to the shells she wore under her suits. Those were the craziest colors and patterns I’ve ever seen. I love a bold print, but even I was like WOW, that’s a lot of neon for someone not teaching an aerobics class in the 80s. There was such a disconnect between those 10 tops and everything else in her closet, and frankly, even her. So, I asked her–what’s up with these. And she essentially told me she bought them to have more style. So, I asked–do you like them? And she said no, but I don’t want to look boring.

This perfectly summed up the challenge that women with simple style often face–your choices are either boring, or so not you that you don’t want to wear it. I saw this countless times.

I loved working with those clients, because one of my favorite things is to show women how they can be stylish AND be themselves–to me, that’s where style magic truly lives. In authenticity.  giving yourself permission to wear things you love and liking the results. That’s when style actually feels sustainable. It’s really tough to dress like someone else’s version of style long term

So today, I want to share with you how I helped those women get the style they wanted, without becoming someone else, and how you can do the same thing. 

I’ve got 5 tips for you, and they are in no particular order, other than that they spell BASIC. It does not mean B is more important than I–it’s just that B comes before I in basic. Here we go:

B–B stands for “beauty” ...and honestly, I can hear it now–”Jen, I just said I don’t want to be fussy, and your solution is a complicated beauty routine”? Hang on sister, hear me out. I am not talking about going full Kardashian here, but the truth is, style doesn’t just exist from your neck to your feet. It’s the whole visual package. So what beauty, in this case, means is finishing your look from head to toe–in a way that honors your desire for simplicity.

Look at all the pictures of women looking put together in jeans and a tee–you know something they have in common? Their hair looks good. And again, I’m not saying you have to get a fresh blowout at Drybar once a week, I’m just saying that styled hair goes a long way in looking put together. 

Even if you are the lowest maintenance woman on the planet, there are some easy, tiny things you can do to punch up your beauty routine and look more polished.

For example, I’m guessing you put moisturizer on your face in the morning, right? Even if you don’t wear makeup? What about swapping it with a tinted moisturizer tinted sunscreen?. Or trading your basic lip balm for a tinted lip balm. Both of these things don’t require you to do anything extra, and yet the results are noticeable.

If you always wear your hair pulled back, what about pulling it back with a pretty clip–or better yet, talk to your stylist about a cut that’s easy to style so you don’t have to wear it back all the time. Same thing with color–ask about low maintenance hair color. 

Again, adding a little finish to your style through beauty doesn’t mean you have to spend an hour a day on your makeup, but a little effort goes a long way. I’ll be the first to admit I don’t do a full face every day, but I do tint my eyebrows and eye lashes once a month. It takes less than 10 minutes to do both, but then even on days I don’t wear makeup at all, I still look somewhat put together. Every time I do it, I’m shocked by what a big difference it makes. 10 minutes spread out over the course of a month is what, like 20 seconds per day? I don’t care who you are, you can’t call that high maintenance.

Next in our Basic formula we have A, which stands for “accessories”, and again I can hear it “Jen, are you not listening? I said I’m simple, that means I don’t want tons of accessories” And again I say “hear me out”, because the reality is, there are some accessories you have to wear, and that’s what we’re going to start with. You don’t have to wear stacks of bracelets or statement earrings, but I’m guessing you do wear shoes, right? You probably carry some kind of handbag, right? That’s what we’re talking about–upgrading the accessories you can’t avoid wearing. It’s a really good place to start. 

I’m going to switch to tough-love mode for a moment–and I want you to know I truly do care about you, but I just need to say this, and I hope you forgive me. There is some connection between wanting simple style, and loving frumpy shoes and handbags. I don’t know what it is, I haven’t studied the phenomenon in-depth, but I do know that not wanting to be bold, or fussy, or over the top doesn’t HAVE to equate to looking frumpy and dated, but too often, it does, and in large part because of the shoes and bags. Solve this problem, and you’re halfway there. 

I think part of this has to do with the idea that simple style isn’t about trends and constantly updating, and that’s fine, BUT everything dates, and some of these things weren’t stylish in the first place.  And I know this is where people want to know if their bags and shoes are frumpy and what makes them frumpy, and honestly, it could be a lot of things. It could be structure–too much or too little–hardware and embellishments, color, material, condition shape…there’s no way to tell you all the things, or cover all the combinations of the things. If you’re in the style circle, send in your pics for style coaching, and I’ll tell you honestly, but for now, what I need you to understand is that understated can be stylish and beautiful, especially in accessories, but you’ve got to choose items that feel refined–and let the simplicity do the work. 

The fewer things you wear, the more each piece stands out–that’s a big theme of simple style, and we’re going to come back to it again later–so choose pieces that elevate your whole look instead of drawing it down.

The idea of upgrading your daily accessories can also be applied to things like watch bands and belts, and if you wear glasses, consider your frames as well. If you’re wearing it, it has an impact on your outfit, whether you want it too or not, and I guarantee there’s a version that is not over the top and bolder than you want to be that will give more polish. And no, you don’t have to choose between comfort and style. You might have to look a little more, but you don’t have to choose.

Now for those of you who do want to accessorize with things like necklaces or other jewelry, simplicity is actually on your side here. For a few years now, understated accessories have been trending. The bubble necklace days are gone, and they’ve been replaced with smaller, simpler pieces that will give your outfits just a little bit more finish without pushing you out of your comfort zone. 

But just start with upgrading the things you have to wear anyway. 

Moving on to S in our BASIC formula, we have styling touches. 

What I mean by this is things like tucking your top, cuffing your jeans, scrunching or rolling your sleeves, letting a tee peek out from under your sweatshirt or sweater, or buttoning a cardigan differently to see which one looks best–like just one button at the top, or a few buttons in the middle. 

Styling touches are small, intentional adjustments to clothes you’re already planning on wearing that cost no money, take very little time, and don’t require you to add anything extra. It’s just about taking 30 seconds to see what you can do with your clothes to make them look a little more finished. To make them look like an outfit. 

You don’t have to do all of them, or any of them–some outfits don’t need it, and some pieces look less refined when you start messing with them, but give yourself one minute to try. 

A really good exercise is to go to Pinterest or do a google image search for woman jeans and t-shirt or woman jeans and sweater. Ignore anything that looks more styled than you want to be, or has too many accessories or layers–I looked at outfits that just had a top and a bottom. That’s it. Then I honed in on which ones looked put together, and which didn’t. Compare the polished, put together ones, to the ones that don’t look elevated. What are they doing? What styling touches are they using? I think this is actually better on google than Pinterest, because no one puts frumpy outfits on Pinterest–you get a better variety and more comparisons on Google, but do what work for you.

You’re going to find that these little things make a big difference.

Moving on to I in our formula, we have INTERESTING BASICS. 

One of the hallmarks of simple style is a love of basics, and I get it, I love basics too. They’re an important part of any functional wardrobe, but too many basics, and too many basic basics will leave your wardrobe looking boring and bland. 

The fix is not to go wild and buy blouses and blazers instead of t-shirts and cardigans…it’s actually a whole lot easier than that. Here it is–buy more interesting t-shirts or cardigans. A waffle knit or a rib knit instead of a plain tee. A boatneck instead of the old faithful crewneck. One of my favorite pieces from the winter capsule guide is a long sleeve tee with a little bell sleeve. Not enough to be annoying, or fall into my plate at dinner, but enough to look elevated and purposeful.

Like I’ve mentioned already, so often women think that the solution has to be an extreme departure from what feels natural, or what they’re comfortable with, when the reality is, these little baby steps are sometimes all you need to from underwhelming to understated. 

One of the biggest things you can do with interesting basics is realize that your jeans are not neutral. By neutral, I’m not talking about whether or not they go with a lot of stuff, like black or white or other neutral colors. In that respect, jeans are a neutral–they go with everything. By neutral in this context, I mean that they have no effect on your outfit. Your jeans are not neutral. A pair of dark wash flares has a really different effect on the way your outfit looks than a pair of light wash baggy jeans. I’ve noticed that a lot of women who want simple style tend to only wear straight leg jeans in a slightly darker than medium wash. Nothing wrong with them, but you’re missing an opportunity to use different washes and silhouettes to create more intentional outfits–without doing anything complicated, or adding more clothes. 

One thing I’ve said a lot over the years is that if you’re a jeans and a t-shirt woman, be a jeans and a t-shirt woman–just buy more interesting jeans and t-shirts. Don’t try to become someone else, just elevate the styles that feel natural to you. 

The last stop in our basic formula is C–which stands for Condition. Meaning, do your clothes look a little shabby and worn? Remember before when I said that the fewer pieces you wear, the more each one matters? Right here friends. Especially when those pieces are simple. You’re going to notice the pills on a solid, unadorned sweater more than you would on a fair isle sweater, for example.  When you’re just wearing that ol' t-shirt and jeans, a faded color or stretched out neckline stands out more. 

Simple ladies tend to go for more natural fibers and wear a lot of cotton, and that’s great. But it tends to fade and lose its shape faster. Doesn’t mean you have to ditch it, it just means you have to be aware of it. 

One of the biggest challenges with condition from normal wear and tear is that it happens slowly. Like if I spill bleach on my clothes, or get an annoying olive oil spot on something when I’m cooking, I notice it immediately. But things like color fading, or pieces losing their shape or their recovery happens slowly. So slowly we don’t notice it. Often, we don’t notice a sweater is pilly until it’s REALLY pilly, or that a color has faded until it’s REALLY faded…and that probably means your clothes have been looking shabby for a hot minute. 

Really, the only fix for this is to start looking at your clothes every day with a critical eye, and having your clothing care tools handy. This is one reason I steam pretty much everything I wear every day, and have a lint roller and fabric shaver handy. It takes no time, but when you’re looking at the shirt before it’s on your body, you tend to notice these things more. Plus, they’re easier to fix than before you’re wearing it. And also, wrinkles are polish killers. I know they happen throughout the day, and with fabrics like linen, often there’s not much you can do–BUT you don’t have to start the day looking rumpled and sloppy. 

Thinking that your clothes only have to look nice when you’re going somewhere special is the same thing as saying style only matters when you’re going somewhere special. If you spend the majority of life doing everyday, unspecial stuff, do you really want to spend the majority of your life looking shabby and worn? I gotta say, that doesn’t make sense to me. Not when it’s so easy not to. Like, you don’t need to know how to dress your body, or what your best colors are—you literally just need to run a steamer and a lint roller over your top. 

I think that’s a great example of how we think style is a whole lot more difficult than it really is, especially when it comes to simple style.

It’s not about bold outfits, or complicated routines, it’s little things that add up to make a big difference, and make your simple outfits look the way you imagined in your head. 

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

First, there’s nothing wrong with simple style. You do not have to become someone you’re not in order to look good.

But, when you wear fewer pieces, and those pieces are basic, every single one of them matters more. There’s just less to look at, and fewer things to distract the eye.

The best place to start is by upgrading the things you’re already doing and wearing. From elevating your beauty routine, to finding shoes that help your outfit instead of hurting it, the key is to just start where you are. That will help you still feel like you, which makes style sustainable.

Your homework is to pick a couple of these things and focus on them for the next couple of weeks. Doesn’t matter which, and you don’t have to do all 5–pick the ones you think could have the biggest impact on bringing your simple style to life, and do those. See what a difference it makes.  Looking like Jennifer Anniston in jeans and tee might be closer than you think. 

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!