Pencil skirts can be formal, strict, classic, professional, ultra feminine and bombshell, which is fabulous if that’s how you want to wear them. They can also be playful, casual and relaxed with the right support act. These outfits showcase ways of doing just that. Mix things up by creating tension and interesting juxtapositions. Feel free to change up the colours and patterns so that they’re more to your taste.

IMPORTANT:

  • The strength of the pencil skirt is its structured slim silhouette, which makes wearing just about any silhouette of top or topper a flattering and streamlined-enough option.
  • Pencil skirts vary from straight to very tapered on the side seams creating a tube-skirt effect. Take your pick.

1. Playfully Heeled

I like the tension between the severity of the pointy-toed, glossy, dressy, heeled boots and the relaxed and gentle vibe of the roomy cardigan. The flowered pattern and billowing sleeves add a dash of romance. The knit top adds a little more softness, which in turn complements the hard-edged shaved head of the model. The tucked top adds polish and lengthens the leg line from the thighs upward.

New Neoprene Pencil Skirt

2. The Comfy Touch

The pattern on this pencil skirt is playful in itself, and accentuated with the addition of the comfy sweatshirt. The layered white shirt is an interesting detail, but not essential. The flat high-shaft haute hiking boots throw in a ‘90s integrity, and the white laces magically pick up the white in the rest of the outfit. You could wear a less oversized sweatshirt, leave off the white shirt, and semi-tuck into the pencil skirt instead. Throw in a dressy shoe and Bob’s your uncle.

Zara Midi Skirt

3. Haute Hiking in a Bomber

The tension between the tight tube skirt and relaxed bomber is interesting. Sporty Bombshell. The layering top is a simple long-sleeved tee or pullover worn over the skirt. Feel free to leave off the belt bag. The haute hiking boots add back a ‘90s touch, and the scrunched shuffle socks above the boots bring back the ‘80s. I’d have preferred to see a beret or beanie for a hat, but the felt fedora is unique.

Scotch & Soda Knitted Skirt

4. Relaxed Elegance

This pencil skirt here is less tapered and dressier than the first three looks. The roomier pencil skirt complements the oversized pullover thereby matching the relaxed effect. Semi-tucking the front adds some structure, as does scrunching the sleeves of the pullover. The black-on-black creates an elongated column of colour. The naked silver sandals look seasonally confused with the pullover to my eye – cold feet! But I love the way the silver magically bookends the model’s silver hair. Silver pumps, Mary Janes, pointy-toe ballet flats, or booties would have been my choice of shoe. Gorgeous look.

J.Crew Slip Skirt in Burnout Velvet Leopard