Creating playful ensembles with pencil skirts is an ongoing project with many of my clients because tight pencil skirts are often thought of as overly corporate, strict and bombshell, especially when they are matched with a classic pair of black pumps. Of course, there is a time and place for strict corporate pencil skirt outfits, and it’s a great look for some specific work environments. But there’s also room for a less serious pencil skirt outfit in a more casual setting. So with de-bombshelling strategies and colour top of mind, we’re going to tickle that pencil skirt until it laughs right back at us. Choose one or more of the following tactics:

  • Wear it in a colour
  • Wear it with a roomy top that’s less expected than a tailored and tucked button-down shirt
  • Keep the footwear lighthearted

Playful Skirt Ensemble

The components of the ensemble:

  • Pencil Skirt: A non-neutral pencil skirt tends to look less serious. Choose brights, pastels, mid-tones or jewel tones. A neutral pencil skirt is an option, as long as its support act has a sense of humour.
  • Roomy Top: You have many options, and here are four to get you started (from left to right in the picture). Wear them untucked.
    1. Sassy Sweatshirt: Choose a fashionable sweatshirt with a banded bottom for extra structure, and scrunch the sleeves. This is the fashion forward option that’s a touch sporty.
    2. High-low Pullover: Choose one in a fine gauge knit, and scrunch the sleeves. It’s on trend and very comfortable.
    3. Swing Top: This one’s more flirty and ideal for hot weather. A sleeveless style adds structure to the outfit.
    4. Drapey Top: This is the arty option with added drama.
  • Footwear: The point is to stay away from a conventionally corporate look, so if you’re going to wear pumps, wear them in fun colours, white, and sci-fi metallics. Or wear ankle strap sandals or caged wedge sandals. And for Team Flats there’s slipper flats or gladiators.
  • Accessories: A daytime clutch is a great option, but so is a satchel, tote or crossbody. To my eye, light neutrals, metallics and non-neutrals are generally less serious than black or dark brown bags. Add jewelry as desired and eyewear as required.

I’ve left out a jacket to keep the vibe a touch relaxed. Peasant blouses, oversized boyfriend shirts and silky tees are more options for tops. And apart from the slipper flats, I’ve kept the ensemble solid. But feel free to add pattern in any one of the outfit components. Pattern mix to your heart’s content! That in itself is a playful styling concept.