Many of my clients enjoy wearing a tailored pencil skirt outfit because the combination generally looks dressy, professional and flattering. But they don’t necessarily want to look too dressed up and bombshell, which is often the case when you pair a formfitting pencil skirt with a tight top and pair of heels. So we look for ways to “de-bombshell” the pencil skirt for days that require a more relaxed vibe. 

There are many ways to relax the pencil skirt, and I’ve started the ball rolling here with three tonal renditions. The oversized pullover is at the heart of de-bombshelling the outfit. The ensembles become more casual from left to right. I’ve used solids, but by all means incorporate patterns and use any colour palette. Pairing the pencil skirt with the same colour pullover creates a two-piece dress effect, which I personally think is a great look. 

Here are the components: 

Pencil Skirt: Choose a pencil skirt, either dressy or casual, at a length that tickles your fancy. Some pencil skirts taper more dramatically at the side seams like a tube skirt, which adds more structure to the outfit and curve to your silhouette.  

Pullover: Choose a fluid or oversized pullover in a chunky or fine gauge. Choose a style with a neckline of your choice. Roomy pullovers with asymmetrical hems, high-low hems, split hems, and welts tend to work best because they add a little structure to the slouchy integrity of the top. Semi-tucking a fine gauge baggy pullover, thereby shortening its length, works well if the pullover is long. Scrunching sleeves to reveal forearm skin adds further structure. 

Swingy pullovers with a trapeze silhouette look quite nice over pencil skirts. Their volume is on the hem as opposed to the torso. 

Footwear: Pumps and ankle strap pumps are fab dressy options. Tall tailored boots with heels are great too. Heeled booties are easy, and wedged booties dress the look down even further. Pointy toe flats and loafers are another way to go. 

Wearing heeled booties with a notched and narrow ankle opening creates a longer leg line. Feel free to wear hosiery that matches the colour of the booties, or your skin tone. 

Accessories: Finish off the look with a bag, eyewear, jewellery and watch as desired. A bib necklace works well over a fine gauge pullover.

Here’s Olivia Palermo sporting the look with a semi-tucked slouchy burgundy turtleneck, pencil skirt, ankle strap pumps, clutch and bib necklace. Choose a trench coat or longer wool coat as a topper.