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7 Habits of Highly Stylish People

By Carol

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You know those individuals you see at work, in the mall, or walking down the street who look effortlessly put together? You wonder how they knew to combine the prints they’re wearing or the bold color combination they’re rocking so confidently? The truth is, creating a confident image is not about wearing the latest trend or high-end label. Developing your style takes time and will come as a result of some trial and error.

Looking polished and stylish isn’t about a ton of clothes or dropping a lot of cash, but it’s instead a mindful practice. Here are seven habits of the highly stylish you can develop to become your own style icon.

What they wear reflects who they are.

Those who have a confident image and strong personal brand developed it based on their authentic essence and clarity of their vision and goals. They know their best colors, favorite prints, how to accentuate their best features, and dress for every occasion. Their wardrobe is an outward reflection of who they are on the inside. It supports their goals and attracts desired clients and opportunities. This is why they exude so much confidence when you see them walking down the street.

They build upon their wardrobe every year.

You don’t build your wardrobe on trends but you stay current by staying “on trend.” The difference is having an eye on colors, style lines and silhouettes (pant lengths, sleeve shapes, necklines, etc.) and wardrobe combinations. They know when their outfit and style are dated their skills, knowledge, confidence, competence and abilities are perceived as outdated or lacks relevance. As a result, stylish people will look to add a few new pieces to their wardrobe every year.

They’re not afraid to try something new.

It’s easy to get into a rut in your wardrobe. Some suffer from what I call the “Garanimals Syndrome” and can only wear certain pairings in their closet. To only wear pants, dresses or skirts, or worse…to only wear black will keep you from feeling confident and stylish. When you know how to dress your body, your right colors, fabrics and patterns, and you dress with purpose and intention you’re not afraid to try new pairings, patterns or color combinations in your closet. You’ll learn to do it effortlessly without a second thought.

They don’t pay attention to sizes and are more concerned with fit.

Label sizes and fit, in many cases, are not the same things. Manufacturers cut garments based on a variety of fit standards, many of which aren’t built around true body sizes. As such, those who are rocking a confident image don’t pay attention to size labels and pay more attention to how a garment fits their body. Sizing up in one store or down in another is not a stressor.

They have a tailor on speed dial.

The reason size labels don’t matter is because they have a tailor or seamstress on speed dial. This allows for everything in their closet to have a custom fit and why they look fabulous without really trying.

They don’t shop, they invest.

Functional wardrobes are made up of 80% workhorse pieces and classics that will last from season to season. Those with a confident image don’t buy just because it was a bargain nor do they wear uncomfortable items because it has a designer label. Whether purchased from a consignment shop or Neiman Marcus, they successfully utilize the cost-per-wear formula, sales, wardrobe planners, high-low styling, and their custom color palette to build a powerful wardrobe. This ensures wearability and versatility.

They don’t copy bloggers or magazines, but they do get inspiration.

This may appear contradictory but highly stylish people don’t dress to be highly stylish. They dress for themselves, their lifestyles and what makes them feel amazing. Copying outfits, colors, or the styles of bloggers or fashion magazines is not the goal. Knowing what works best for them, those with a confident style find inspiration but interprets it through their style lens.


As you can see these habits aren’t revolutionary but they can be rather hard to follow. It’s easy to be overwhelmed by all of the fashion data out there, but if you embrace these seven habits you’ll become your own style icon in no time.

Need help incorporating these habits into your daily lifestyle? I work with women who want a to develop a powerful and profitable confident image. If that’s you, then schedule a FREE Session with me for the new year!

Live, laugh, and confidently shine!

Carol 😉


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About The Carol

I'm a 50 years young curvy fashionista enjoying my "second life." I'm a wife, mom of 3 and 1 goldendoodle. I'm a recovering attorney, accidental professor, successful jewelry stylist, and ...