Trend Alert: How To Nail the Ladylike Look This Season

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Get ready for a demure winter.

If you watched Mad Men for the fashion (who didn’t?) and were partial to Joan’s aesthetic, I have great news for you: One of the biggest trends of the season is the ladylike look. Think everything Joan encapsulates with a sleek, modern edge. If you’ve noticed a resurgence of fitted jackets, slingback kitten heels, and midi skirts and dresses, you’re already aware of this fad. Major fashion magazines have reported on it, including Vogue and Women’s Wear Daily.

I’m here to help you nail the ladylike look this winter. 

It’s a little retro, a la Jackie O., but young women are making it their own with bright makeup and avant-garde shapes. The best part is you get to reclaim the word “ladylike,” which was weaponized against rebellious women for so long.

If you’re looking for items that fit this feminine, preppy, and put-together aesthetic, look for the items mentioned above, as well as generally opting for fitted apparel — don’t be afraid to turn to your tailor to get the measurements just right. Collarless and cropped blazers, A-line skirts, scarves, structured totes, peacoats, and elegant belts all fit the bill. Cardigans and capes work, too. Even retro sneakers and polo shirts count as ladylike. Don’t forget accessories — like dainty timepieces or pearl jewelry. For textures and patterns, think tweed or suede, with accents like buttons or bows. 

If you’re done with the drowning-in-your-clothing trend, your time has come: Get ready for a demure winter. 

I’m exploring two of my favorite elements of this trend in the videos: Fitted jackets and slingback heels. 

We’ve also compiled some items that fit into the ladylike category for you to shop below.

Ladylike Fashion