November 9th, 2015
It Item

Monday Must-Have

The return of a 90s sartorial staple, the slip dress, is a trend I will embrace wholeheartedly—it’s an easy piece to layer. Tuck a turtleneck underneath, top with a chunky cardigan, and go. Any shoe of the moment works with this look and add Wolford tights, or over-the-knee boots, when it’s too cold for a bare leg.

Styling tip: If the slip dress needs a slip, wear the slip under the turtleneck.

Tabitha Simmons Mary-Jane, Jacquemus Beige ribbed top, Theory slip dress, slip dress, Gucci brown loafer and here, Gucci black loafer, slip dress, Chloé Cardigan, J. Crew black turtleneck, Gucci mule and here.


what's new




Leather jacket


Cropped corduroy pants


Able boot




Embroidered bag


Shearling-lined boots




Mini tote


Sweater dress





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  • Very timely post, Preston. Trying to style around a midi slip dress for an upcoming weekend in NYC – can you recommend a boot to wear with it?

    CatNovember 9th, 2015  6:35 AM

  • I’d wear black tights with loafers, or an over-the-knee boot.

    PrestonNovember 9th, 2015  6:43 AM

  • that long sweater is everything! so cozy.

    midnight snark

    kimNovember 9th, 2015  8:07 AM

  • Great round up of items. I wish I could wear those Tabitha Simmons shoes – gorgeous.

    KathyNovember 9th, 2015  8:24 AM

  • Very timely post. I have seen this look popping up on the streets of Toronto. A lacy slip dress layered with a nice old fisherman’s sweater and over the knee boots is my favourite. Loafers are great with this look too.

    KarenDNovember 9th, 2015  8:26 AM

  • I’m intrigued by the look of the slip dress with loafers and a sweater. Any good pics of this look?

    AprilNovember 9th, 2015  9:26 AM

  • April, I’m going to wear this look with my Saint Laurent loafers, that was the inspiration. Sorry, no street style pic to add to the post.

    PrestonNovember 9th, 2015  10:53 AM

  • Thanks, Preston. I like the idea of a loafer with a little heel. Cute look!

    AprilNovember 9th, 2015  11:07 AM

  • I have that Organic John Patrick slip dress in navy that I love. One of the keys to a great slip dress is the length. Right below the knee or midi length is best in my opinion.

    zoeNovember 9th, 2015  11:43 AM

  • It sounds like a great outfit but I’m having a hard time picturing this one. I haven’t seen it on the streets here, perhaps its not cold enough yet for the layers?

    micheleNovember 9th, 2015  12:34 PM

  • I like exploring and freshening up the styles of past decades, but I’m going to have a hard time embracing the return of the mid 90’s!

    EBNovember 9th, 2015  1:33 PM

  • I’m having a hard time imagining how a slip dress could ever be warm enough, regardless of the layers added. And if I managed to add sufficient layers, even in So Cal, how I could not look incredibly lumpy with undies, tights, a sweater causing static electricity . . . I just don’t see it!

    Tori MordecaiNovember 9th, 2015  8:52 PM

  • Fond memories from the slip dress days…I think it’s a timeless, sexy and versitile look. The updated ribbed turtlenecks and loafers are always chic, but that Chloe sweater is calling my name, but my wallet is not listening.

    KWNovember 9th, 2015  10:38 PM

  • I just love all the Gucci shoes ! Also, the slip dress seems to be having a moment, and I might just fall for it as well 🙂

    CarolineNovember 11th, 2015  11:18 AM


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