So You Hate Your Skinny Jeans but Love Your Boots, What to Wear?

  • "I'm really into this dress — the shape is super feminine and I like the length. If I wore it in real life, though, I'd swap out the high boots for a flat option. I think longer dresses with flat boots is a good look. It's very Elaine Benes — someone I aspire to look like every time I put on a dress!" - Simone
  • Yet another ringing endorsement for the J.Crew tissue turtleneck.
  • Side note on Simone's awesome hair: Her secret is loads of conditioner and a special comb comb for knots. "It's called a Tangle Teezer, and is basically a dog brush marketed for humans. I use that in the shower, and just let it air-dry. We shot this in the morning. By the end of the day, when my hair is fully dry, it's about twice as big. I like it more frazzled so I don't put oil or cream in it."
  • "While the ‘70s print on these pants is not something I'd ordinarily wear, I love the crop. I think a flat boot keeps the look in check." - Simone
  • "I love overalls. I have three pairs from this old school western-wear company Round House. Though these are fun, and feel more appropriate for the office. If anything, I'd go for an even baggier shape." - Simone
Alison Syrett | March 22, 2016

Sorry to your Apple Bottoms

Once upon a time, skinny jeans were all I wore.

But sometime between 2014’s reemergence of vintage Levi’s and the culottes that came after, I went from wearing cigarette cuts every day, to a few times a week, to feeling repulsed by the idea, which made wearing my vast collection of boots made just for tucking feel impossible.

Can’t I have my baggy-fit trousers and eat my boots, too?

No. That would be painful. Keeping my favorite kind of footwear around, however, isn’t. Allow me to present a three step plan:

1. Stop thinking in terms of just pants.

3.1 Phillip Lim dress, Topshop boots, J.Crew turtleneck, Olympia Le-Tan x Muzungu Sisters clutch
3.1 Phillip Lim dress, Topshop boots, J.Crew turtleneck, Olympia Le-Tan x Muzungu Sisters clutch

A pair of over-the-knee boots shields one’s legs from the bipolar temperament of early spring weather with all the efficiency of trousers but in a less expected way. To squeeze every last ounce of visual interest from this look, opt for a midi skirt that’s slit just enough to show off extra tall shoes. Thanks to the perfect balance of proportions and shapes, it’s like a wearable Instagram filter, guaranteed to turn every movement into a post-worthy shot.

Speaking of great shots, by the way, meet our lovely model for the day, Simone Kitchens! She’s the associate beauty director at Glamour where she also contributes features, and she, too, is ready to give skinny jeans a breather.

“I was sent a press release last night for some plastic surgery treatment claiming to make ‘every day a skinny jeans day,’ which is maybe the most depressing email I’ve gotten this week,” she said. “That’s my idea of skinny jean fatigue. When doctors are trying to change your body to better fit a jean trend, I’d say it’s time to move on!”

2. Move on we shall — to cropped trousers!

Johanna Ortiz dress, Edun pants (similar style here), NECKLACE TKTK, Paula Paula Cademartori bag (similar style here), Everlane boots
Johanna Ortiz dress as top, Edun pants, Everlane boots, Paula Cademartori bag

Fashion may be reaching peak culotte, but crisply tailored, just-above-the-ankle lengths still feel fresh. The proof is in the pinstripe pudding that are these flood pants and the way they hover just so above Everlane’s contrast sole sneaker boots. Because there are so many neutral colors and straight lines happening in the lower half of this look, we went full fiesta up top. This is a chance to mix bright red, puffy sleeves and a butt cape without looking like a superhero sidekick. Take it!

3. Prefer something more subdued? Bust out the overalls.

TKTKT OVERALLS, J.Crew turtleneck, Everlane sweater, Doc Marten boots
Frame Denim jumpsuit, J.Crew turtleneck, Everlane sweater, Dr. Martens boots

It’s an easy way to satisfy your denim craving without singing that same old skinny jeans song. The best bibs of the moment, in my opinion, are reminiscent of jumpsuits with sleek, clean lines and a dark wash finish — a sly, sexy of wink to the Western trend — and ideally paired with Doc Martens. Because the clunky-cool silhouette doesn’t match any of the stereotypes so often associated with all-in-one dungarees (farmers, mechanics and pre-schoolers — oh my!), it lets the look be a blank canvas on which to paint your own style.

So what are you waiting for, Picasso? Get to it!

For more fashion and beauty inspiration from Simone, you can find her on Twitter here and Instagram here; Photographed by Krista Anna Lewis.


  • ooo these looks got me DYING. So inspirational. I want it all.

    • Hattie Selden

      When I looked at the draft of 5889 dollars, I have faith that brother of my friend was like really generating cash in his free time with his PC…yiv His aunt’s neighbor has done this for only 11 months and by now repaid the loan on their home and bought a new Car.

      For Details Click Here

  • AhhhhhYeah!

    Don’t forget option 4.
    Wearing black thong, black bra, and your hair in a pony tail.

  • love the second look!


    • Deanna Matthias

      When I looked at the draft of 5986 dollars, I have faith that brother of my friend was like really generating cash in his free time with his PC..uo His aunt’s neighbor has done this for only 11 months and by now repaid the loan on their home and bought a new Car.

      For Details Click Here

  • Charlotte

    Gorgeous! And so are the looks!

  • I tried my skinnies just yesterday but my legs screamed out ‘Claustrophobic!’ so I switched into mom jeans….

    • Aydan

      my boyfriend jeans made a resurgence this past weekend, I was surprised at even myself

  • Ariana H

    Hyperbolizing a mental illness (to describe the weather, nonetheless) is not only harmful to those with said illness, but also incorrectly perpetuates a myth that bipolar is a one-size-fits-all illness. Not everyone with bipolar disorder has rapid mood swings. By trivializing their experiences, by making it seem like an everyday adjective, you make it hard for people to take others seriously when they actually have that disorder.

    • lemonruby

      “bipolar” has a meaning outside of mental illness textbooks:



      having or relating to two poles or extremities.

      “a sharply bipolar division of affluent and underclass”

  • Abigail

    i like the dress w/ OTK boots idea!!! are there any rules/guidelines to wearing a dress with a turtleneck underneath? i know leandra was obsessed with those tissue turtles from j crew last year and i’m hoping to transition some of these into spring… thoughts?

    • I have a few sheer-ish ones for COS that I wear under almost everything! It adds a cool grunge/mod look depending on the dress and accessories. I wear them under… tent dresses, sun dresses, smock things, fit and flare dresses, literally all the dresses.

  • Melissa

    SO good. Simone is killing it.

  • Rachel Coleman

    Love this. It’s so true that skinnies are not what we reach for on a daily basis; I certainly don’t anyway!