Reinvent Your Personal Style for the Back-to-School Season

Forbes

10 hours ago

Maddie Orlando wears Kaia sip vest and skort. Artless Forever
In the blink of an eye, we're going to be in the thick of 'back-to-school' season and while some may lament at the notion of scaling back one's personal aesthetic, think of it as more of an opportunity to reinvent your style and engage in a thoughtful 'refresh'. Education in the classroom is the obviously priority, but school is also about self-discovery, learning about your personality, and continuing to finesses your sense of style as the years progress.
I speak with founder Maddie Orlando of it-Girl brand Artless Forever about embracing the 'learning process' of reinventing your personal style. In being the founder of this ultra popular brand, and a fashion creator with a strong online presence—she is a go-to source for style advice. 'Artless is rooted in effortless minimalism and is simple by design, encouraging our customers to use their pieces as a starting point to develop their own personal style. Being a clothing designer also requires me to predict trends before they happen, which means I'm always in the know about what's coming next,' she explains.
Invest in staple wardrobe pieces—then mix and match with accessories for versatility and to showcase your personality. Artless Forever
'Personal style is the development of your own distinct approach to fashion. It's the ability to recognize what silhouettes, colors, pieces, and accessories suit you best, and then remain true to them, regardless of what is trending,' she says. Think of it as being an extension of your personality, 'it's a physical and visual expression of individuality and allows you to communicate who you are without having to say anything at all,' adds Orlando. Ultimately, it's about honoring your true self, 'cultivating personal style is essential because it fosters authenticity, and with it, the confidence that comes from truly celebrating yourself as an individual,' she says.
Layering is key when it comes to navigating different social environments. This Eloise tank and maxi skirt can be worn for outings with friends and then at school when paired with a cardigan, as an example. Artless Forever
Think of it like a sort of New Year's Resolution where one makes a mental checklist of accomplishments and goals to achieve, 'the first few weeks of a new semester set the tone for the rest of the year and are the perfect time to pause for a moment of self-reflection: who do you want to be and how do you want to show up this school year? Establishing your personal style early on is a great way to communicate this to others,' says Orlando.
Additionally, when meeting all the unpredictability that school life throws at you, control can also be found through one's aesthetic, '...developing what I describe as a 'uniform' makes it so much easier to get dressed, streamlining those often busy mornings before class,' she says.
Stunning classic A-Line Mini Dress that's flattering and form-fiitting is a piece you'll wear time and again. It can be dressed up on down with accessories and footwear. Artless Forever How to Identify Your Personal Style
How you look and feel in your clothes is key to this kind of vetting and self-assessment: 'Everyone has certain styles, neck lines, hem lengths, shapes, and colors that they feel most confident and comfortable in. Spend an afternoon auditing your closet, trying on a range of different pieces and determining what you look and most importantly, feel, best in,' she says.
There isn't a one-size fit formula, so to speak—but don't be afraid to mix and match, '...this (exercise) will be different for everyone! The key is to develop a go-to outfit formula that works for you, and stick to it whenever you get dressed or shop for new pieces in the future,' Orlando offers.
Easy skirt and Tank is layered with white linen pants for a chic contrast and the look is completed with a belt to further play with silhouettes and texture. Artless Forever Tips for Experimenting with Your Style
Tinker and play with embellishments, 'start with accessories. I love to keep my outfit simple but experiment with a trendy necklace or colorful shoe,' says Orlando. This not fun way to repurpose wardrobe pieces without automatically feeling compelled to shop for new items—it's also layering onto your core aesthetic, 'this way, I never stray too far from my classic look, but still get to play with pieces that are a little more fun and exciting,' she explains. Top Personal Style Trends for 2025
'Plaid, polos, the skinny flare pant, capes and ponchos, big buggy sunglasses, slouchy purses,' she says. Building a Personal Style That Works for School
Layering is key to appeasing to different environments without losing yourself in the process, 'for example, adding a cardigan or jacket over a simple outfit is an easy way to elevate and individualize your outfit, while still sticking to school dress codes,' she offers.
And don't be afraid to pull out those accessories again, 'you can also play around by adding a belt, pair of shoes, glasses, or jewelry that suit your personal style,' Orlando says.