4 Layered (Gen-Z Approved!) Looks.

winter layered looks

When Carly suggested we do a post about layering, I was all for it, but wanted to let her run with it as truthfully, layering is not my strongest suit. I do better with dresses than I do with separates… and I sometimes go overboard with the layers and wind up looking like a haphazard fashion version of the Michelin man. It’s tricky! Carly pulled together these four looks and honestly? I love them all!

I love that she incorporated a lot of my favorite pieces into these looks (the Boden Loafers, my favorite button-down and t-shirt) but her taste and style shines through. The end result is a perfect hybrid of our individual styles. It also made me think of this article in the NY TImes: Millennials Don’t Know What to Wear. Gen Z Has Thoughts, which I really loved. Below, four Gen Z suggested (but Millennial approved!) layered looks.

Which one is your favorite?

4 Layered Looks (Gen-Z Approved!)

The Art of Layering

art of layering - denim on denim

Layered Denim

Grace: Denim on denim is something that has always intimidated me a little bit but this version feels really wearable and if I might add, elegant, even? The denim pieces err on the more classic side and the tailored black coat, boots, and belt make it feel sophisticated, not schleppy! While this look is the furthest one from my personal style, it has me thinking I need an oversized denim jacket to layer under my more tailored, ladylike jackets.

Carly: There is honestly nothing I love more than a good Canadian tuxedo. But this layered look goes above and beyond, and feels so approachable for so many different generations! Having spent a part of my career with Max Mara I really benefited from the personals we could pull each season, namely this fitted denim shirt. The wash of the denim paired perfectly with jeans that had been withering away in the back of my closet, and thus my love for a layered denim look was born. I fell in love with the Boden belt and cutaway tank combo for this too.

monochromatic look

Tonal Color

Grace: OK this one feels easy to me. It’s elegant and chic and makes me think of The Swans (who else is watching?). This outfit inspire me to shop my closet, to be honest. I love a monochromatic look and this one slays.

Carly: As a lover of all things brown, this look is right up my ally while still feeling elegant and very on par with Grace’s closet! I am a BIG skirt girl and fell in love with the wool material of the Loeffler Randall midi. A perfect winter wardrobe staple!

Related: Winter Knitwear Edit

how to layer a Turtleneck

Tailored Turtleneck

Grace: This feels like another easy one! I fully plan on wearing this exact outfit. I have been seeing turtlenecks styled all over the runways and in my favorite fashion substacks. The key I think is to get a really thin turtleneck; one that is meant to be layered. And you want a button down that isn’t too fitted but also isn’t too oversized. For me, the Sezane Max Shirt checks all of the boxes. It’s roomy without being overwhelming. I have all sorts of thoughts on button downs and probably own too many but my thought is that if you are going oversized, you need to show some skin. If you aren’t doing that (turtleneck), you don’t want to go to big!

Carly: Arguably my favorite layered look! Because its so simple you can really lean into the accessories to make it your own. My immediate first thought when I sourced this look was to pair it with a kitten heel slingback and a colorful sock. BUT to encourage Grace to take a walk on the wild side, I threw in her FAVORITE Boden loafers (seriously we talk about them non stop) and topped it off with some Chimi sunglasses (which I’ve taken note of how much she loves them too). I’ve actually worn a variation of this look several times this winter but opted to finish it off with a gray sock to match my gray turtleneck, and these vintage Prada mules (which my dog has since ate so they’re off at the shoe doctor).

4 Layered Looks (Gen-Z Approved!)

Day to Night

Grace: See, this is where I, the elder millennial, get tripped up. I love everything about this look but don’t want to put a t-shirt under my top. It feels wrong to me, but I also know it looks fresh. I might try this. I am not sure. But Carly has sure made it tempting as she incorporated my favorite Loewe bag and a Reformation top I’d been coveting.

Carly: This look was actually deeply inspired by our videographer, Faith. She is so effortlessly beautiful and loves to show up to shoot days in the most stunning tailored tops. I love how all of these pieces can feel high or low, depending on how you style them. Grace and I are suckers for a good white tee, so I wanted to challenge us to style it for a day to night look since we’re both always on the go.

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Leave a Comment

Leave a Comment


  1. Elle:

    Would be so helpful to see these looks on! I’m interested but it’s hard to capture the mechanics of some of them without seeing (ie how does the button down collar layer w the actual neck of a turtleneck?) Thanks!

    2.7.24 Reply
    • Elizabeth:

      Plus one to this! Would love to see these looks on. They are truly all so good.

      I’m also curious if you know how the Sezane white button-down compares to the AYR one?

      2.7.24 Reply
      • I don’t own the AYR white button down but I had some of their striped ones and would say the Sezane one is a bit longer which I appreciate!

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        • Elizabeth:

          Thank you! Appreciate the short feedback.

          2.7.24 Reply
          • Elizabeth:

            Shirt, not short πŸ™‚

    • Marissa:

      I third this. I love the looks, but it would be so helpful to see them put together and being worn by Grace and Carly!

      2.7.24 Reply
      • I’ll try πŸ™‚ not going to add this to Carly’s plate but I share my daily outfits on Instagram and Substack!

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        • Jean:

          What is the blazer/coat in the top/title photo? J’adore.
          I am always on the lookout for an oversized blazer, so if that’s a blazer, i’m tap dancing with joy.

          2.18.24 Reply
    • I always share my IRL outfits on instagram and substack so you’ll see them there πŸ™‚

      2.7.24 Reply
  2. m:

    Fun post! I like skirted look number two the best as baggy jeans are where Gen Z throws me for a loop. Give me a beautiful skirt with tall boots and a sweater that doesn’t need to be tucked in and I’m a happy (and comfortable) older lady feeling put together. I too am loving the sumptuousness and tailored look of The Swans.

    2.7.24 Reply
  3. Laura:

    I clicked through to the GAP trousers and it reminded me the Zac Posen has just signed on as the lead creative for GAP brands which I am very excited about! I love him as a designer and think these partnerships have been good for GAP in the past, like when they brought on Patrick Robinson.

    2.7.24 Reply
  4. Leanne:

    I loved these! As an elder millennial who wants to be in style but doesn’t want to return to the low rise cargo pants of my youth, this was actually helpful, haha! Ordered the Boden loafers today – you’ve sold me on them!

    2.7.24 Reply
  5. Lauren:

    I also want to see these outfits on you! Love the idea of figuring out how to modernize my wardrobe and style but really really need to see how this all works together

    2.7.24 Reply
  6. I love the idea of this, though it would have been more helpful to see the outfits in action. Anything can look good on a product collage but then look silly once on.

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  7. Michelle:

    This was so helpful! I layered my white Ayr button down over a mock neck for work today!

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  8. Sofia:

    I loved this post! I live in a city where it gets cold so a turtleneck under my button down is one of my favorite styling tricks (in fact I’m wearing it today!). The look reminds me of Diane Keaton for some reason, even though I have no proof that she’s ever worn this look. It’s just something I *think* she would wear πŸ™‚

    2.8.24 Reply
  9. This is so helpful to me as my daughter is GenZ and I’m clueless about fashion. I notice that the color palette is subdued, which does match her taste.

    2.8.24 Reply