This ensemble is for Team Skirt. It combines the ladylike and bombshell vibe of a tight midi pencil skirt with the casual and sporty ease of a bomber jacket. The juxtaposition is fun and a little unexpected. Note that a midi pencil skirt is knee-covering, and looks best when tapered quite severely at the hem. The outfit will not have the same dramatic and elegant effect if you wear an above-the-knee pencil skirt. 

Choose any colour palette, and feel free to create a column of colour under the bomber. I’ve chosen high contrast pieces with brights and patterns, but a neutral look in solids is just as fab. The renditions on the left and in the middle are pretty, while the rendition on the right adds a little hard edge. Go with whichever vibe tickles your fancy. 

Here are the components:

Skirt: Choose a midi length pencil skirt that is tightly tapered at the side seams. That way you’ll create adequate structure when wearing roomier tops and flats. And your skirt will stay put as you stride. Lengths can vary from just over the knee to further down the calf. Knitted pencil midis are best, because they stretch as you stride. Tight woven midi pencils skirts are quite hard to walk in, so I vote knitted all the way. 

Top: Think fluid tees, tanks, high-low blouses or peplum tops. A crew neck, V-neck, or scoop neck works best with a bomber jacket. A tee creates a more casual look. A blouse creates a refined and dressier vibe. A black leather peplum adds some edge. Wear the top untucked or partially tucked. 

Bomber Jacket: You’re after a sporty bomber jacket in a woven or knit. Lace works too. Scrunch the sleeves and wear the front open to create a slimming vertical line down the front of the body. 

Footwear: Your choice of footwear seals the deal. Pumps, ankle strap pumps and caged sandals are pretty and office appropriate in some environments. Slipper flats and d’Orsay flats are trendy and super for Team Flats, and particularly elongating with a pointy toe. Cut-out and peep-toe booties add a harder edge, especially in black. 

Accessories: Choose any bag. A fashionable backpack is a fun option and amps up the sporty vibe of the outfit. Finish off the look with jewellery, watch and eyewear as desired. 

It’s an easy outfit to pull together and you might be able to shop your closet for the look right away. Nice for some office settings, or for a casual night out. No jeans required. 

I passed on my woven midi pencil skirt a few years ago because it was too hard to walk in. Now I’m in the mood for a knitted pencil midi so that I can pull together the look with my lace bomber and pointy toe ankle strap pumps.

Pencil Midi and Bomber Jacket