I love to ask women to describe their style in three words. The words they choose say a lot about how they see themselves, and where they are on their style journey.

I call those three words Style Guideposts, and they’re the secret to effortless style.

What are Style Guideposts?

Style Guideposts are the 3 words that describe the way you look. For example, if you overheard someone talking about you, and they said something like, “I love Linda’s Style…she always looks so blank, blank, and blank”.  Those “blanks” would be your Style Guideposts.  They could be fun, bold and eclectic or even refined, elegant and sophisticated.  Either way, they describe how you want to look. 

A couple of things to keep in mind about these magic words:

First, the words you choose are completely subjective.  Your idea of “feminine” may be completely different from someone else’s, and that’s ok. As long as you understand what the words mean to you, and you can identify pieces that fit the bill, you’re good!

Also, your Guideposts need to be authentic.  They should be a true representation of the way you want to look. Not how you think you should look. 

Don’t say, “I should be elegant and refined” if your style is really fun and eclectic.  Your Guideposts need to ring true to you in order for them to be helpful.  

Can you use them to help change up your style? Sure, we talked about that in our episode on Reinventing Your Style, but at the end of the day, trying to dress like you think you should, instead of how you want to look, is a losing battle. 

Style Guideposts are important because they make it easy to shop, get dressed, and edit your wardrobe. They keep you on the right style path–you know, like a guidepost.

Have you ever been shopping and got distracted by good deals and fun things but then didn’t wear any of those deals? It’s probably because they weren’t really your style. 

A clearance skirt isn’t going to turn you into someone you’re not just because you bought it and didn’t pay a lot. So test your purchases against your guideposts.  Do they match at least two of the three?  It’s probably going to be a good buy. If they don’t match any of your words, you can safely put it back. 

When you’re getting dressed and you want to up your style game, use your Guideposts. If your words are current, fun, and polished, like mine are, ask yourself if your outfit for the day is current, fun, and polished. Again, it should hit at least two of the three. If your outfit doesn’t match your words, what can you add or swap to get there?  That is how you end up with outfits that feel like outfits. 

Style is a skill, and if it’s not one you’re naturally good at, but you want to be–this little habit will have a big impact.

Finally, use your Guideposts when you’re editing your wardrobe. You know those insurance clothes you’re hanging on to, convinced you’re going to want to wear them “someday”? If they’re not your style, you won’t reach for them, so you can let them go. 

Hopefully, you can see how these three little words help make style, and wardrobe building, so much easier. 

Sometimes, however, women choose words that make style more difficult.  When I ask women to describe their style, the top three answers I hear are all words that can lead to style confusion. 

Those words are Comfortable, Casual, and Classic. 

Here’s why you should reconsider using those words as your Style Guideposts.

Comfortable is Not a Style

“Comfortable” is the most common word we hear, but it’s a problematic style descriptor because style is how you want to look. If someone says, “That looks so comfortable”, chances are oversized sweats and pajamas come to mind, right?  Not the cute, pulled-together style most women want to have.  

But, that doesn’t mean you can’t have a comfortable wardrobe.  It simply means you should shop with the way you want to look in mind. You shop through the lens of what you want your wardrobe to be.  When you define it with a word that’s about function, like comfort, you’re going to end up with a wardrobe that looks that way.

When you define your style as comfortable, your eyes go to things that look comfortable, and you end up with a whole wardrobe full of sweats, leggings, tees–and not much else. However, when you shop through the lens of your style guideposts, you look for clothes that look how you want them to look. For example, you might think jeans are too uncomfortable, so you don’t even look for them.  However, these jeans from Liverpool are the most comfortable pants I own. They also happen to be current and polished–two of my Guideposts. 

Identify clothes that look the way you want them to look, and then choose the pieces that have the comfort you want to feel. You’ll end up with a wardrobe that’s both comfortable and stylish!

Casual Isn’t a Style, Either

As a Style Guidepost, Casual is a little less egregious than Comfortable, but it’s still problematic.  When people say their style is casual, I can kind of picture it. It’s probably jeans and tees, over trousers and blouses. It’s probably more knit fabrics than wovens, sneakers and booties over heels. So in that respect, it might bring up the style you want people to see.  But here’s my issue with it:

Casual isn’t really a style; it’s a level of formality. 

Every life has some casual activities, and every life has some more formal activities. Maybe your life is 90% casual, 10% dressed up, or maybe it’s the other way around, or somewhere in between.  

The problem comes when women who self-describe their style as casual have to dress up. They really struggle.  Like, “I don’t even want to go” struggle. Over the years, women who described their style as “casual” shared stories of times when they struggled to get dressed or spent an entire event feeling underdressed and self-conscious.  They didn’t have as much fun because they hated their outfit. 

When you’ve got something fabulous in your closet, you’re more excited to go to that baby shower or birthday party.  When you struggle to get dressed, the whole thing seems like a big chore. These special moments in life shouldn’t be a chore.  

When you describe your style as casual, your entire wardrobe becomes casual. You start to have a hard time seeing yourself as someone who wears anything other than casual clothes or goes anywhere other than casual places. 

A better approach is to choose three words that describe how you want to look, and then dial up or down the formality level of the pieces you choose based on how you live. For example, I have athleisure clothes that are current, polished, and fun, and dressy clothes that are current, polished, and fun. Using your Style Guideposts will keep you from creating a prison of casual clothes, where you don’t feel confident going anywhere you can’t wear jeans.  

Bonus Tip for my Dressy friends: If you self-describe as a “dressy” person, the challenge is the same–events outside of your normal routine might throw you for a loop, too. The fix is also the same.  Choose words that describe how you want to look, leaving “dressy” out of it.  

Classic Is a Style, But It’s Not What Most Women Mean

Classic is the most misunderstood word of the bunch.  Classic actually is a style word, and a very good Guidepost, but most women who use it don’t understand what it really means.

Classic is a style that is traditional, unfussy, and well-tailored. You don’t find a lot of super trendy pieces, out-there patterns, or oversized, slouchy pieces in a Classic wardrobe. The magic of Classic style is kind of in its subtlety. These are the women you look at in jeans and a tee and think, “She looks so put together.”.  Every piece is nice, fits well, and the accessories are understated and refined.

Classic style focuses on quality over quantity and incorporates a lot of timeless pieces. Classic is characterized by great basics, and lots of neutrals with pops of clear, bold colors like red, kelly green, and lemon yellow. In addition, you see patterns like stripes, plaids, and some leopard print.  Accessories are traditionally understated–like a pair of gold stud earrings instead of big hoops or chandeliers. Key pieces in a classic wardrobe are things like a white shirt, dark jeans, a trench coat, a blazer, ballet flats or loafers, and structured handbags.

If you’re someone who describes their style as classic, but these things aren’t describing your wardrobe or the things you gravitate toward, chances are “Classic” isn’t the right word to describe your style.   

When women use the word “Classic” to describe their style, often they mean “not trendy”. These women want to avoid buying “here today, gone tomorrow” pieces, and they have the idea that clothes are either trendy, and they’ll be out of style next week, or things are classic, and will look current forever.  

The reality is, neither is true. Hopefully, you’ve listened to my episodes on The Truth About Trends, and Are Skinny Jeans Still In, and you know that there’s a difference between trends and fads, and that trends don’t move quite as quickly as we think. But even classic, timeless pieces change over time and need to be reevaluated to make sure they still look current. So often, when women self-describe as “Classic” as a way to avoid “trendy,” they end up looking dated.

I’ve also heard women use “Classic” as a catch-all to mean “I’ve never thought about my style. I just buy clothes and call it classic”. That’s where using it as a Guidepost can actually hinder your style instead of help it.  Too often, women use their Guideposts to describe what’s currently in their closet instead of how they’d like to look.

So if you’d describe your style as classic, first, ask yourself what that word means to you. If you can picture what classic looks like in your mind (Hello, Kate Middleton and Audrey Hepburn), and that’s how your wardrobe looks, you’re good to go. Keep using it.  If you’re using Classic as a Guidepost because you’ve never thought about how you want to look, put “Classic” aside for a bit and finish the sentence: “I want to look blank, blank and blank.”  Don’t think about what you already own, or what you’ve been wearing. Think about how you’d like to look, and find pieces that reflect that.   

We talk about Style Guideposts a lot, and it’s because they help simplify style so much. If you want real, authentic, personal style, just start by asking yourself how you want to look.  Come up with three words that are authentic and unique to you, and then use them to make style easier, better, and more fun. If you’re not sure where to start, take our Signature Style Quiz to get your creative juices flowing.

Listen to the full episode below to hear more about these three un-Style Guideposts, as well as some words to use instead to make your style even easier!

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