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Taylor Tomasi Hill is constantly a go-to source for sartorial inspiration. After all, she’s an industry veteran with a storied fashion career that has led her to her current role as the creative and fashion director of The Yes. (It’s the innovative shopping platform that uses your personal taste to provide daily product recommendations from top brands.) Her fashion selects are often of interest given her experience, fresh eye, and unique sense of personal style. So on that note, we wanted to learn more about one of the items she lives in on a daily basis. Yep, we’re talking about jeans.
Below, you’ll uncover some of the denim silhouettes Tomasi Hill is gravitating toward this fall. She also shared the specific trends she’s teaming with her go-to cuts to create her fresh and forward looks. As a preview, there’s everything from modern tailoring picks to elevated basics coming your way.
Keep scrolling to find a smattering of style references, complete with a digest of the items Tomasi Hill thinks work flawlessly with different jean styles. Oh, and if you are in fact shopping at the moment, there are also inspired items from The Yes sprinkled throughout.
Quilting + Relaxed Denim
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“I like to keep things relaxed, especially when I’m running errands or having an adventure with my son, Wells. Relaxed denim is a good base (comfortable but still cool) and perfect for pairing with happy prints and a quilted jacket. All are from Kule, of course, one of my all-time favorite brands. I’m never NOT wearing Kule.”
Long Tailored Blazers + Baggy Jeans
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“Don’t get me wrong—Re/Done jeans are great as is, but you could wear the combination of a tailored blazer and a Bottega bag with just about anything and look fabulous. It’s a power combo that’ll get you through meetings, long work days, dinners, and beyond. And when it comes to bags, go for red. It’s a neutral in my book.”
Stripes + Baggy Distressed Denim
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“I like taking baggy, distressed denim in a preppy direction. Mix in an oversize striped shirt and some loafers or mules. It’s one of my uniform looks I go to over and over.”
Florals + Two-Tone Denim
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“Denim can be a great neutral, like a clean canvas for grounding bold prints. I fell in love with this quilted Clare V shirt-jacket because of its genius-level print mixing. (Florals and checks? Okay, YES!) It looks super cool with two-tone denim I love from B Sides.”
Exaggerated Silhouettes + Distressed Denim
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“I’ve never been afraid of volume—it’s such a dramatic way to express your style. This season’s exaggerated toppers are by far my favorite trend, especially when done to perfection like this Alexander McQueen army denim jacket. Pair it back to more denim (hello, denim on denim, another favorite trend this season) and wear it with a preppy loafer.”
Embellishment + High-Waisted Denim
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“The best way to make a dressy top feel effortless? Wear it with denim. I love taking a piece, like this tweed-and-pearl gem from Huishan Zhang, and wearing it with high-waisted denim to break things up. The mix of something over-the-top with something really casual keeps it interesting.”
Checker Prints + Loose Denim (+ Puppies)
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“There are some things that are eternally cool, like checker prints. They’ve been cool since ’70s surf culture took root, and I think they’ll always stay cool. Clare V makes the perfect checkered fanny pack, which is a must now that I’ve got my other accessories: puppies!”
Next, check out more denim outfit ideas.