Updated February 2019

unflattering fashion
dress: Kate Spade, shoes: J.Crew, purse: Papaya Art

A large part of my job is lengthening the line of one’s body. This involves v-necks, shorter hems, slim bracelets, ruching, waist-defining anything, and a scallop hem. I do love flattering one’s figure, but sometimes it’s nice to kick the lengthening to the curb and embrace fun garments and comfortable outfits that basically make us look short, fat, or both. My rule of thumb for these unflattering garments is it better be absolutely fabulous and completely comfortable. Here are some of my favorite unflattering fashions that do just that…

Loafers With Baggy Dresses

Loafers with slim ankle pants or the perfect shorts look slimming and stylish, but loafers with almost anything else often makes us look short and stout. Pictured above you can see me swimming in an embellished Kate Spade shift dress and silver and blush J.Crew loafers (similar here). I felt absolutely chic and pajama comfortable in this getup.

A Colorful Muumuu or Vivacious Caftan

A gargantuan flowing colorful drape of fabric that is the muumuu or caftan is fabulous. I am absolutely in love with Dolce & Gabbana’s banana leaf print silk caftan. It’s actually quite flattering considering all the fabric. It is sold out now, but I have fresh new options in the Shop This Post below.


High-Waisted Baggy Pants

The high-waisted baggy pant is notoriously unflattering in the belly or torso area, but occasionally there’s one that makes it worthwhile. In fact, Free People has put out a fantastic crop cargo pant that is fresh, fun and comfortable. Again, it’s actually quite flattering considering what it is. It is sold out now, but I have fresh new options in the Shop This Post above.

Graphic Sweatshirts

Sweatshirts don’t do the body any favors, but the overzealous sweatshirt is one of my favorite things. Of course Kenzo always has some aggressively graphic sweatshirts to share with you. And Ann Demeulmeester has a fantastic black velvet dolman sleeve oversized sweatshirt thing that I love, despite it being black. If you pair it with leggings you will be utterly fabulous, 100% comfortable, and definitely au courant come fall. For something a bit sweeter, try J.Crew’s Save the Elephants Sweatshirt. Update: These are all sold out now, but I have fresh new options in the Shop This Post above.

Bizarre T-Shirt Dresses

With the spirit of the muumuu in mind, bizarre t-shirt dresses are so fun, deeply comfortable, and easy to throw on for a sloppy look that feels like an intentional fashion choice. The Fifth Label has quite the delightful man-repelling t-shirt maxi dress available right now. It’s on sale. I wonder why. Update: It is sold out now, but I have fresh new options in the Shop This Post above.




personal stylist


graphic purse

Photos by Dayley Photography

Make-Up by Antonella Annibale