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Do you feel pressure to “dress your best”?  To stick to the best colors and silhouettes that are traditionally best for your body shape and coloring?  Lots of women struggle to marry the things they love with what the experts say they should wear.  If that sounds like you, I’ve got great news!

You don’t have to dress your best.

In this episode I share why dressing your best doesn’t have to be your goal 100% of the time, and what to do if the things that are best for you aren’t the things you love most. It’s time we take a new approach to “flattering” and expand our definition of “best”.

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Read the Full Transcript below.

Hi Friends! Today I’ve got a short and sweet episode with an important message that I know some of you need to hear, and that is, you don’t have to dress your best.

You’re probably thinking “wait, is this some kind of Jedi mind trick, or reverse psychology thing where in the end, we’ll all want to dress our best”  Nope, it’s not a mind trick and if you want to dress your best 100% of the time, that’s great, but I’m really here today to tell you you DON’T have to dress your best…not 100% of the time if you don’t want to, and frankly, not ever if you don’t want to.  

You might be wondering, “if we don’t have to dress our best ever, why are we listening to your podcast, Jennifer?” and fair point.  The mission of this show is and has always been to inspire women to love the way they look, and to give them to do so easily. That’s it.  Nowhere does it say my goal is to help you stay in this little rule box of dressing your best and being miserable about it. In fact, if you’ve followed along for any length of time, you know that’s quite the opposite

I want to share WHY I’m talking about this today.  Sometimes there’s a theme in my clients and conversations that keeps coming up over and over in a short period and I have to take a pause and talk about it. Lately, what has been coming up is women struggling to dress their best, and it isn’t making them happier. The rules of knowing what’s best and how to get there aren’t helping to make style easier or more fun. 

For the purpose of today’s conversation, when I say “best” I mean what is traditionally the most flattering.  The best necklines for your body, the right dress shape, and length, the best colors for your coloring–all that stuff.  

Lately, it seems like I’ve spent a lot of time with women who KNOW these bests, but don’t LIKE them.  I’ve been working with women whose bests for their body shape have been at odds with their personal style, and women whose best colors are at odds with what they just personally gravitate toward.  They’re stuck in this conflict because they want their clothes to be flattering, but they also want to like their clothes

It’s time to expand our definition of flattering. If a top objectively hides a tummy you don’t like, but it makes you feel frumpy and dated, the top isn’t flattering.  If a color objectively makes your eyes look brighter but makes you feel like a phony, the color isn’t flattering.  Flattering is what makes you feel like the best version of yourself.   Audrey Hepburn once said Happy Girls are the prettiest, and I think that should be every woman’s style mantra. Wear what makes you happy. Wear what lights you up. THAT, my friends, is flattering too.  

The other theme that’s been coming at me for weeks, both through podcast interviews I’ve recorded, and in my personal life is this idea of living authentically, and in alignment with who you really are, and I think style can be a part of that.  If you’re a person who loves all things retro and pin-up girl style and polka dot dresses are your jam, wear them. Even if fit and flare dresses aren’t traditionally “best” on you. Wear what makes you feel like the best, most authentic version of yourself.  

I was watching a video on YouTube a few weeks ago, and it was from a color expert who was answering a subscriber question. The girl in the video had coloring much like mine–light, bright and warm.  Her question was that she thought she looked best in deep, saturated cool colors–like burgundy, and black.  She wanted to know if she was right.  Long story short, no, she wasn’t, and the color expert said as much. But here’s the thing. The girl’s entire aesthetic aligned with black and burgundy. She would have looked ridiculous in the bright coral I’ve got on today. It simply wasn’t HER.  Would her eyes have looked brighter and her skin warmer? Yes, 100%. Would she have felt authentically best? I’m gonna say no.  

But the color expert did say something I thought was very wise and insightful. She said that often people come to her because they want validation of what they want to be true. When she said that, I felt it. I get a lot of that.  People want me to tell them that what they like is best, and I can see the disappointment when I can’t validate that. Sometimes, it’s objectively NOT, and so I can’t say it…just like this color expert couldn’t say black was this woman’s best color.

What I tell these women is what I’m telling you now. You don’t have to dress your best. You don’t need validation to wear what you like.  You can just wear it, knowing it’s not objectively best, but knowing that it makes you happy. 

I have the same conversation with every woman who comes to me because there’s a disconnect between what she feels she should wear, and what she would like to wear, and that is, you simply have to choose what’s most important to you. There’s no wrong answer. Wearing what’s objectively best for you, and wearing what you like best are both perfectly acceptable approaches to style.  When you can’t have everything you want, you have to prioritize what’s most important.  

When it comes to other aspects of our lives, I don’t see women struggling with this concept of “best” quite so much. If you go to a nutritionist and say I feel like pizza and ice cream are the best things for me to eat every day. Am I right?  She’s going to say, no, not even close. You should eat 6 servings of vegetables every day, and have a turkey and low-fat cheese sandwich for lunch. Are you going to leave that appointment and NEVER have pizza or ice cream again because they’re not best?  In reality, probably not. Maybe you won’t make those things the foundation of your own personal food pyramid, but you’re probably won’t be in knots because the things you like the most are not the things that are best for you. A more sensible approach would be to find balance. It’s the same thing in your wardrobe. Find the balance

And now it’s time for Unpopular opinions with Jen, the part of the show where I share an unpopular opinion. I believe that often, women create, or at least embrace this “quest for best” tension as a way of avoiding something, rather than it stemming from a need for perfection.  Sometimes the women I’ve worked with have been avoiding investing in themselves Other times, they’ve been avoiding creating a personal, unique style because they’re afraid of what others will think. Sometimes, they’re avoiding dressing their bodies just as they are right now, so they create this narrative that it’s just so hard to dress my best, I guess I won’t even try.

I’m not saying this is true for everyone, I’m just telling you what I’ve seen over the last 20 years, and i’ll tell you that if you find yourself frequently not buying things because it’s not 100% absolutely perfect, or you’ve convinced yourself that dressing your best is so difficult that you shouldn’t even try.  You’re probably avoiding something and using the “quest for best” excuse.

So if it all boils down to “just wear what makes you happy”, is there a point to learning what’s best?  Yes, and I’ll tell you why.  First, some women truly don’t know. They don’t have the innate sense of “oh, this neckline is better on me” or “shift dresses are e better on me than fit and flares”.  Knowing those things can make finding things you feel good in much easier.  Also, once you know what’s objectively best, you can learn how to tweak it to work for you. As Pablo Picasso said, “Learn the rules like a pro, so you can break them like an artist”. Knowing WHY something works means you can figure out HOW to make other things work for you. So you should know all of those things–and THEN decide what you want to do about them.  At the end of the day, you need to be happy with how you look, and I promise no one will run away screaming in horror if you wear a crewneck instead of a scoop, or the wrong shade of green.  Use the rules to make style easier, but don’t be afraid to step outside of them and create your own definition of best.

There’s no homework today, and We’ll be back next week with an episode on the Style Lessons I want my daughters to learn.! In the meantime, come say hi on Facebook or Instagram–you can find us at everydaystylewithjen on either one.  Bye for now! 

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