How I Transformed My Most “Boring” Staples into 5 Chic Looks
The blue-jeans-and-white-shirt combo is iconic for a reason—it’s simple, effortless, and endlessly versatile. But my favorite thing about it is how many outfits of mine start off with this classic combination. Pretty much every day this time of year, I put on jeans and a t-shirt and let the outfit come together from that no-fail starting point. Lately, I’ve been experimenting with ways to give this duo an upgrade and I’ve finally figured out a few outfit combinations that are an absolute must-try for this season.
Beginning with character-making accessories to unexpected layering tricks, these five ideas breathe new life into my old and trustworthy favorite outfit formula. Here we have the easy outfits to recreate that will make you fall in love with your favorite pair of jeans all over again.
The right pair of jeans and a T-shirt that just makes sense for you are an essential part of this process. These two pieces will be the ultimate building blocks for your perfect wardrobe. These staples are endlessly versatile and will serve as the ultimate foundation so choose wisely. When you find silhouettes that suit your body and style, they become go-to pieces you can rely on for years. For me, I lean towards baggier denim styles that are low-rise and have a long inseam. I tend to look for pairs that puddle at the ankle. T-shirt wise, I also prefer a baggier fit and a boxy struture that stops right at my hips. Investing time in finding your perfect pair and tee is worth it—they’re the secret sauce to effortless, everyday dressing.
Proof that jeans and a T-shirt can feel luxe: gold accents, a chunky knit, and a belt that looks straight out of the ‘90s. Add heeled boots for a little extra height and polish.
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This sweater was so fabulous it's already sold out but I love this burgundy alternative.
My favorite heeled booties that I've been wearing everywhere for over a year now.
Jeans, a tee, and the kind of faux fur that turns heads. I kept the accessories simple because this coat is the moment.
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Who knew my favorite activewear brand could deliver in the outerwear category so perfectly.
Hats are having a moment, and this sailor cap turned pillbox is my nod to the runways. Sometimes, it’s all about the unexpected twist and Mains De Vapeur delivered in this case.
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Denim on denim has always been a favorite of mine. The suede belt with a bold buckle ties it all together—cowgirl, but chic.
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Channeling CBK with a tortoise headband and a red tweed jacket—classic, polished, and a little ‘first lady’ energy.
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Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of experience in the fashion industry to the editorial team. Since joining Who What Wear in 2021, Sierra has made her mark by expertly blending luxury and accessible fashion content. Whether she's decoding the latest runway presentations or crafting a perfectly curated shopping list, Sierra's keen eye and relatable approach have solidified her as a trusted voice in the fashion space. She's also reported on major industry events like Paris Fashion Week and lent her expertise to red carpet coverage, ensuring her audience gets an insider's view of the most glamorous moments in style. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. Her ability to translate editorial expertise into viral social media content sets her apart, seamlessly bringing her articles and personality to life for a new generation of readers and followers. A graduate of the University of Notre Dame, Sierra brings a unique perspective to the fashion industry that is informed by her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.