Pencil skirts can be ultra flattering and streamlining, but I personally find that wearing a flared skirt is a lot more fun. The swoosh of the skirt as I stride puts me in a good mood. Skirts with movement get bonus points because they allow you to walk at a faster pace and feel more comfortable. 

  • J.Crew Crossover wrap skirt: A front wrap skirt that glides along the contour of your hips and thighs. The wrap crosses over a little further than other skirts in this silhouette which makes it less revealing when the vent falls open as you sit down. But do the sit-down test just to be sure. Combining the skirt with black leggings and a black top is another option.
  • Topshop Textured Box Pleat Midi Skirt: Dramatic and pretty with a fun texture.
  • Whistles Skirt - Asymmetric Hem: An A-line wrap skirt in the shape of a kilt. Breezy, flattering, and best with a tucked top. Beautiful on pear shaped ladies. Best on those with a smaller waistline who can fill out the hip and bottom area. Not as good on an inverted triangle or apple shaped body type.
  • Free People Skirt - Printed Show You Off: Swooshing boho chic galore. Great length on tall gals.
  • DKNY Laser-Cut Full Midi Skirt: An architectural flare in a laser cut looks a little tougher than a flouncy style in a floral. I like the alluring exposure of the leg due to the short lining. Beautiful with a black support act.
  • Club Monaco Tundi Skirt: The fabric is sublime. A little like a Shantung silk but a lot more robust. Drape is gorgeous and the fit is snug on the waist.
  • Nona Wrap Maxi Skirt: A roomy wrap pencil skirt is a genius design. Casual, feminine and drapey. Covered yet alluring. Super soft cozy fabric. Read the rave reviews.
  • Dessie Midi Skirt: A stunning floral pattern. It's a LOT of skirt and quite dramatic so consider yourself warned. Best on a curvy figure with a small waist and round hips. Might run a size small.
  • Club Monaco Nuria Skirt: This skirt is a '90s blast from the past. I can see it worn with moto boots and a cropped jacket. Delicate and drapes very well. Nice asymmetrical seaming.
  • Classiques Entier Floral Print Cotton & Silk Skirt (Regular & Petite): Retro Deluxe in fabric, shape, colour and pattern. Love the pockets. It's also available in petites, and you might need to size down a size.
  • MILLY 'Cascade' Midi Skirt: A dramatic sculputural beauty that is a little restricting to wear, but the flounces and front vent make the style feel a lot freer than a regular pencil skirt.
  • Trouvé Trouvé Pleated Metallic Midi Skirt: A pleated skirt with an ombré effect. It's not a slimming style, but it IS interesting and unique. Good length for tall gals.
  • Komarov Print Handkerchief Hem Skirt: An easy style to pair with white and denim. It works surprisingly well on both a curvy and straighter body type. The asymmetrical hemline is flattering and provides ample structure.
  • Bailey 44 'Shadow Waltz' Skirt: A tulle midi for your inner ballerina. Read the rave reviews. Available in three colours.
  • Boden Pandora Skirt: A romantic soft floral flared skirt in pretty pastels. Gorgeous swoosh as you stride. Runs a little small. Check out the other colours.

Pairing tops with flared skirts can be tricky, so here are thirteen top options to pair with the silhouette. And here’s a summary of how to achieve flattering proportions with skirts.

Visit the collection page to see the items alongside my descriptions.