Kendall Jenner’s preppy, retro, vesty street-style in NYC: super-cute or blah?

Kendall Jenner brings the striped sweater vest back into fashion!

Kendall Jenner was in New York over the weekend and the paparazzi seemed especially happy to see her. I wonder about the paparazzi industry in New York specifically! Did they just not work at all during the pandemic? Were they only going out a few times a week to stake out Sarah Jessica Parker’s townhouse or something? Anyway, Kendall was out running some errands in this ensemble and there are about a million photos of her and even Vogue was praising her retro-Annie Hall vibes as the presumptive look for spring:

Kendall Jenner’s winter look was all about quiet minimalism. She spent much of the colder months wearing discreet pieces from The Row. Head-to-toe black was her style M.O., decked out in luxurious turtlenecks, trousers, and coats. But that was last season—for spring, the model has a spring new look. At least, so far.

Spotted in New York City earlier today, Jenner embraced retro-chic. She wore a crisp white shirt and layered a ’70s-inspired striped sweater vest overtop. Jenner paired it with khaki green trousers, brown square-toe loafers, and ribbed socks. The whole look has a grandpa vibe to it. But her tortoise sunglasses, beaded mask chain, and Burberry Olympia bag made the fit feel whimsical and youthful.

[From Vogue]

What’s weird is that I actually like Kendall’s look too? I’m sure the youths probably think that they’ve discovered something wholly new, but the whole menswear-inspired/vest/loose-preppy look was really popular in the 1970s, and it comes back every few years. It really works on Kendall specifically because of her body type (which was also very popular in the ‘70s) and her general Ali McGraw vibe.

Kendall Jenner spends Sunday with friends in sunny NYC

Kendall was also photographed at dinner at Carbone. I kind of like this dress too!

Kendall Jenner steps out in black and white dress for dinner at Carbone in NYC

Kendall Jenner steps out in black and white dress for dinner at Carbone in NYC

Photos courtesy of Backgrid.

Related stories

You can follow any responses to this entry through the RSS 2.0 feed.

18 Responses to “Kendall Jenner’s preppy, retro, vesty street-style in NYC: super-cute or blah?”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. Pusspants says:

    Yuck to both outfits. She looks like a tool.

    • cheesehead says:

      Exactly! she is the blandest Kardashian, and the nastiest. My friend works at the BH hotel and says. she is just the nastiest human.

      • ChloeCat says:

        Oooh, Cheesehead, any stories? I’d love to hear them! I would imagine she’s as vile as they come.

      • cheesehead says:

        @chloecat, The other sisters are darlings except for the two youngest. They are entitled. They would come in at 14-15 expecting to be served liquor and would always have the brattiest attitudes towards staff. The whole “dontcha know who I am?” was reinvented by the Jenners. They tip $20 on a $500 tab, and their lousy excuse is that eating there brings the hotel publicity. You arent allowed to talk to Kendall. Ever.

    • GRUEY says:

      I hate this. I hate aughts fashion. What’s next? Cropped satin cargo pants, kitten heels and spaghetti strap tops? Vom!!

  2. Tiffany says:

    I want those penny loafers.

    That’s my reply.

    *goes off to Google*

  3. nicegirl says:

    She does have a general Ali McGraw type look! I never noticed it before, what the heck!!?? Good eye

    • BothSidesNow says:

      Ali McGraw and whats-his-name were on CBS Sunday Morning and Ali is stunning, still!! She took my breathe away!! They were covering the movie Love Story and how it was an enormous film and by today’s conversion of inflation it netted over 1 billion dollars! God, she is stunning still!
      If you get a chance, look up their interview.

  4. Ann says:

    I like the style just hate the colors. I for one love a nautical preppy look. I’d take the the Ralph Loren version of this outfit in a heartbeat.

  5. ChloeCat says:

    That second outfit is a dress? It looks like she’s not wearing pants, cover your ass! Oh wait, I forgot, she’s a Kardashian-Jenner, my bad!

  6. Lucy says:

    Basic. Not referring to the clothes.

  7. NotSoSocialButterfly says:

    Starting in ‘blah,’ and moving immediately to “nah.”

  8. TaraBest says:

    Ugh, it’ll be a huge pass for me. When I started working in banking right out of college sweater vests over button down shirts was the look. I shudder to think of ever wearing that again.

  9. Nicole says:

    I would wear this outfit today. I would switch out the sweater tho. Horizontal stripes are not my friend.

  10. SpankyB says:

    I like both looks, they look good on her. And I agree, very Ali McGraw. I don’t know that I would wear any of that, though. Probably the pants.

    • Southern Fried says:

      I feel exactly the same. I generally like what Kendall wears and think she makes a great model. Seriously want those pants. Off to online search/shop.

  11. Silent Star says:

    Reminds too much of the mean preppy girls in my 1980s junior high school years. No thanks.

    Although I think it would look ok with different pants, maybe dark jeans or something more fitted with thicker material.

  12. A Fan says:

    Love the first outfit! And she looks great in it, too.

    The second outfit is blah. Actually, yuck would be the word. Too much like what her sister, Kim, would wear.

    [*Tacky.*]