When it comes to model-off-duty style, few of fashion’s current It-Girls do it better than Kendall Jenner—and her street style is proof. Whether she’s shopping in New York City with her sisters or is spotted on her way to dinner with friends—or her boyfriend—in Los Angeles, Jenner has curated a pretty stellar wardrobe that relies on a lot of staples that everyone can pick up for themselves right now.
I’m talking about pieces like baggy graphic tees, tailored shorts and black knee-high boots. These are the kinds of items that you buy once and own forever, so they’re often worth the splurge. It’s time to get shopping, people!
Sure, buying a bunch of trendy pieces can feel exciting at the start of every new season, but that high can wear off fast. More often than not, you’re left having to buy an entirely new wardrobe every time the weather changes. I don’t know about you, but I certainly do not have the budget to be doing that these days. I’ll be sticking to Jenner’s simple fashion rules from now on, thank you very much!
Every modern-day fashion girl knows that the secret to having a real, clear, sense of personal style is to own a few simple pieces that look timeless year after year. Once you have those items nailed down in your collection, you can always add in a newer accessory or two to make any outfit feel instantly modern. If you’re on the hunt for some Jenner-approved pieces that are on the trendier side, consider buying a pair of chunky dad-inspired sneakers or a slender pair of black sunglasses this season. The model has actually been spotted wearing similar items recently.
I personally love Jenner’s slew of high-glam looks on the red carpet or on the runway at Fashion Week, but there’s something about her street style that just draws me in and makes me want to copy just about everything she wears.
While her little sister Kylie prefers to go full-out all the time with her looks, Kendall takes a much more chilled-out approach to getting dressed. But honestly, it makes sense that she would opt for a more laid-back look on her days off. You need a break from the glam sometimes, right?
Yes, she does tend to wear a ton of neutral colors like black, cream and tan, but she also adds in a few pops of color or patterns—she loves shades of bright blue and zebra-style prints, for instance—to keep her daily looks from feeling too simple. The resulting outfits never feel overly planned out, even though I’m sure that many of them are. Leather trousers also seem to be a favorite, which proves that just about any item can be worn during the day or at night. It just depends on the styling!
Read on to check out 10 of the cutest ‘fits that Jenner has ever worn to use as some pretty serious inspiration right now.
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In 50 Shades of Tan
File this outfit under: Reasons To Not Wear Black All The Time. Jenner styled this tan pair of high-waisted leather pants with a pair of coordinating kitten heels and a tight cropped tank. Her on-trend ruched handbag makes this simple ‘fit feel fresh.
In An Oversized Blazer + Knee-High Boots
If you’ve been dying to wear white pants this summer but you’re not totally sure how to do it right, let this picture of Jenner be your guide. She masters the all-white look by wearing a few pieces that come in slightly different shades of white and cream because yes, there are different shades of the hue!
In Black With A Pop of Blue
Like I said, Jenner loves a leather trouser. she styled this particular pair with a bright blue cropped turtleneck a black shacket-style top. White dad-inspired sneakers and the teeniest Louis Vuitton handbag complete the outfit.
In A Shimmery Nude Mini Dress
When Jenner dresses up, she clearly goes all-out. She was spotted in this shimmery David Koma mini dress back in 2019 and inspired a thousand dupes. My favorite part of her outfit, though? The clear Amina Muaddi heels.
In Preppy Separates
Even the coolest girls have an inner prepster, as evidenced by Jenner’s outfit at the Wimbledon Men’s Final in London back in 2019. She styled a powder blue button-down shirt with a pair of tailored white shorts, both of which were designed by Ralph Lauren. But, to prove that she’s never too overdressed, she finished off her ‘fit with a pair of white Adidas sneakers.
In Leather Trousers + A Baggy Tee
No one does day-off fashion quite like Jenner. She wore a dainty zebra-print purse with a baggy white graphic T-shirt and a pair of lived-in leather trousers. The square-toed boots complete the look. This borrowed-from-the-boys outfit is such a vibe.
In A Sleek Black Mini Dress
Kenny stopped traffic in New York City’s SoHo neighborhood when she stepped out in a sheer back mini dress by Ports 1961 and a pair of knee-high black boots back in 2019. Her STAUD Moon Bag is still so chic, even now.
In A Full Leather Look
Leather pants can work for everyday wear—just ask Ms. Jenner! The secret is to opt for a pair that has a looser fit in the leg and to style it with other low-key accessories. Oh–and a matching trench coat helps, duh!
In A Sunny Orange Midi Dress
This is also exactly what I wear when grabbing a soda from the deli! Kenny made headline news when she wore this orange tank dress by Bec & Bridge and honestly, I can see why. She paired the piece with some strappy bejeweled heels and a white Prada bag.