Ways To Build Confidence Through Your Personal Style

Building Your Confidence Through Personal Style
Photography: Courtney Cutting




Let’s just get real: Finding your personal style is a job and a half. If you’re not familiar with the fashion landscape, where do you even start? The older I get, the more I see the importance of crafting a personal style. Whether you’re a working Betty or a stay-at-home warrior, personal style is expressed in every avenue of life. Fashion is more than the finding and styling of trends. It’s about styling the pieces according to your personal aesthetic and lifestyle. Every trend, every silhouette, every high heel isn’t made for everyone. You might not realize it, but personal style is intricately tied to self-confidence. 

I recently hit a style plateau over the past few months.  As a fan of neutral palettes, straight silhouettes, and flats, my wardrobe became increasingly predictable and less reflective of my character.  It got boring. and more importantly, I felt boring.  To paraphrase Kat Williams, self-confidence is confidence of your motherfuckin’ self and nobody can influence that. So I fixed it.  It took a complete closet clean-out, a few bad silhouettes, and several failed attempts at being trendy for me to find my new style and confidence again. Statement colors, smooth fabrics, and playful lengths took center stage as I plowed through the TOBI website to find beautiful spring dresses to get me out of my rut. 

Below are a few things that spring to mind when I think of the ways I’ve built confidence from my personal style recently. 




If you’re not having fun, what’s the point? Challenge yourself to constantly play with prints, fabrics, colors and silhouettes. You don’t have to embrace every trend to truly enjoy what you’re wearing and how you look. Use fashion as a way to express to the world who you are, not how you fit in. My eyes are always attracted to those having fun with fashion instead of the woman with every trend of 2017 on her person.


When I tell you I seek inspiration everywhere, I am not lying. My personal style, much like my personality, is a combined effort of everything I come in contact with. Instagram is a great platform, but don’t be afraid to ask that girl on the train where her stunning handbag is from. Take a moment when you’re getting your morning coffee and notice those around you; what catches your eye? You can’t craft your style if you don’t know what you like. There’s nothing that inspires me more than seeing other women in flawless outfits about town. Don’t be afraid to invest in a new trend or buy those brightly colored shoes.


Ellie Rose Skater Dress x TOBI
Yardley Lace Up Heeled Sandal x Sam Edelman






When you’re comfortable, you look and feel better. Don’t force yourself into heels if you don’t like them. A choker isn’t cute if you can’t breathe at work. Being stylish don’t mean forcing trends on yourself. It’s about finding yourself in the chaos and making your own path. It is extremely noticable when someone isn’t comfortable in the clothes they are wearing, so don’t be that person.









If there’s one rule to live by, it’s this one. I love to enhance assets I’m most confident about, instead of focusing on what I want to hide. One of the great aspects of style is the ability to play up different assets, at any time. If you’re loving your new pastel hair, play it up with a minimalist outfit. Got a great manicure? Stack on several thin rings to play it up. Focus on what you love instead of what you prefer to hide, and you’ll see your confidence in fashion start to grow.


Burgundy BodyCon Lace Dress x TOBI
Nude Heels x Steve Madden


Right now, mine are these gold bracelets pictured above. Each season I think it’s vital to have a signature piece that makes you feel invincible once you put it on. With a signature piece, you instantaneously personalize any outfit. It becomes a direct reflection of you. It’s tied to you. Your statement piece doesn’t have to be a permanent fixture season after season. You can change it to playfully accent your personality or changing the season because, after all, isn’t that the point?


Jersey Shift Dress x TOBI
Denim Jacket x American Eagle




What tips do you use to radiate confidence through your wardrobe?
I would love to know what tricks you use to make your style more reflective of your personality.

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