How I Transformed My Most Boring Staples Into 5 Chic Looks

sierra mayhew styling different outfits
(Image credit: @_sierramayhew)

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.

sierra mayhew styling jeans and a t shirt

(Image credit: @_sierramayhew)

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.

sierra mayhew styling jeans and a t shirt

(Image credit: @_sierramayhew)

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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sierra mayhew styling jeans and a t shirt

(Image credit: @_sierramayhew)

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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sierra mayhew styling jeans and a t shirt

(Image credit: @_sierramayhew)

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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sierra mayhew styling jeans and a t shirt

(Image credit: @_sierramayhew)

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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sierra mayhew styling jeans and a t shirt

(Image credit: @_sierramayhew)

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
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. 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. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.