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Outfit Formula: The Pencil Skirt

Finding an affordable, high-quality pencil skirt isn’t easy. Often they are too short and tight-fitting. Or they are a perfect fit but over-priced.

But a Ponte skirt, like our featured skirt from Boden, in a comfortable stretch-knit, can be dressed up or down, and it is under $100 in all sizes

Like some of our other Outfit Formula posts, I’ll expand on as the seasons change. Because it’s a classic basic, there are so many ways to wear it. 

My inner-nerd is delighted by this formula because it shows how you can start to think about all the ways you can style something to get true versatility. Which, to me, is when you can create completely different looks with a few pieces.

Remember, a good rule of thumb is to be able to wear your better basics three different ways. 

As we build out our 52 Outfit Formulas, you’ll notice that pieces repeat themselves – because that’s the point! You don’t want a closet full of one-off purchases.

So, for example, a shoe you pick up one week will float throughout many of these outfits to give you ways to wear that as well. 

Key Piece: Classic Pencil Skirt

Ponte Pencil Skirt, $85

The kind of skirt you wear is important. 

As much as I recommend breaking up “sets,” in this case, if you have a few skirts that were part of a suit, don’t wear them. You’ll end up looking like you’re wearing a skirt from an old suit. 

I like this one from Boden, available in navy and black, in sizes 2 – 20/22 also in petite sizes. 

I’m happy to see skirts come back into our everyday wardrobes. When the pandemic started in 2020, skirts were the first category I saw fall off our shopping radar. 

Then, styles changed, and all of those terrible Little House on the Praire skirts and dresses hit the racks, along with mini skirts I wouldn’t be able to bend over in.

They’re still out there, they are still terrible, but a least we also see the return of the slim, knee-length skirt. 

Below is a Basic Formula to focus on: 

As I mentioned, there are dozens of ways to wear a pencil skirt.

This formula works off a “column” of color, and then gives two looks with a simple change of accessories. 

Here it is brought to life:

Pencil Skirt Formula 

navy ponte skirt, navy cowl sweater with either white low top sneakers and leopard crossbody bag or a camel wood coat, tan leather tote, tan suede heels, and two tone hoop earrings

Skirt, $85| Sweater, $69 | Sneaker, $99 | Crossbody Bag, $75 | Wool Coat, $250 | Block Heel Pump, $160 | Tote, $198

The base of this look is a slouchy monochromatic sweater. I’m using a cotton-blend sweater, from Caslon at Nordstrom. Available in XXS – XXL.

Since the skirt is fitted, we’re playing with proportion and using a slightly oversized knit that we’ll half tuck into the waistband.
So cute.
You’ll get two completely different looks by changing out the shoe and bag and adding a coat.


Navy Ponte Skirt, Navy Cowl Sweater, Leopard Canvas Bag, white sneakers

Skirt, $85| Sweater, $69 | Sneaker, $99 | Crossbody Bag, $75

This outfit is so simple yet on-trend and modern. 

Grab a crisp white sneaker – and of course, the kind of sneaker matters.

Because of the length of the skirt, you need to wear a low-top sneaker. This will help elongate your leg. And it needs to be an “outfit” sneaker, not a gym sneaker. 😉

I’m using this pair from Sam Edelman just under $100. I like the shape and ease of them. 

Then all you’ll want is a sporty bag. Many of you grabbed this crossbody from Boden earlier this week. It’s leopard print with a navy stripe strap, so it works perfectly here. 

That’s it! Add your everyday jewelry and your set. So easy!


Navy Ponte Sweater, Navy Cowl Sweater, Camel Wool Coat, Tan Leather Tote, and Tan suede Shoes, and two tone hoop earrings.

 Wool Coat, $250 | Block Heel Pump, $160 | Tote, $198 Skirt, $85| Sweater, $69 | Earrings, $45


I haven’t worked in or visited an office in over two years, and I have no intention of returning.
But, now and then, I do miss dressing up for work and pretending to be Miranda Priestly. You can’t deny how amazing it is to feel powerful in your clothes.

Yoga pants just don’t give the same vibe.

So, if I was heading to an office, this is a look I would love to wear.

We’re using the same column, same half-tuck, and throwing on a neutral tan overcoat. I would celebrate it and drape it over my shoulders just to be extra.

I’m using a tan wool-blend coat from H&M, also available in this gorgeous rusted orange. I’m have several H&M coats and am a big fan. Their quality is impressive and they fit true to size.

These suede Marc Fisher block heels have popped up in our Formula’s before. They have a pointed toe that elongates your legs in a skirt, with a block heel that gives some extra balance and comfort. 

Then, I used this sleek tote by Rebecca Minkoff, that is just under $200

And finally, these small mixed metal hoops from Ann Taylor

Outfit Formula: The Pencil Skirt

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Sunday 6th of February 2022

What would you wear on your legs? Nude stockings? Tights?

Megan Kristel

Monday 7th of February 2022

Whatever option you're comfortable with.


Friday 28th of January 2022

Megan, I am so enjoying this series! Can hardly wait every week for my email!

Ellen Dusault

Thursday 27th of January 2022

Love these looks, but what type of stockings or tights do you suggest with each look - it's too cold to go bare legged with the sneakers, and navy tights with the work look seem a bit too monochromatic to me.


Thursday 27th of January 2022

Megan, I know you don't tell women what they "should" or "should not" wear, but how to wear it best. But...can you tell me if a longer legged pear shape like me can wear a pencil skirt? I have always loved the way they look, and it's usually on someone with a more slim hip-or maybe I've been looking at the wrong pictures.


Thursday 27th of January 2022

Would you do a post on tucking in tops? I love the look of the half-tuck but always feel like I look silly. Any suggestions?


Thursday 27th of January 2022

What about hosiery?

Laura S

Thursday 27th of January 2022

Meg! I might even wear a skirt with this weekend look of yours, and I am a pants girl who will be back in the office… possibly never. My “slouchy monochrome sweaters” are pilled and nasty. Suggestions?


Thursday 27th of January 2022

@Laura S, Try a sweater shaver. Pilling happens almost immediately from rubbing, on almost all knit sweaters, including cashmere, and wool. I hope this helps.

Megan Kristel

Thursday 27th of January 2022

What about a simple cashmere option? It doesn't have to be overly slouchy, just like a menswear fit?


Thursday 27th of January 2022

Where on your knee should a pencil skirt hit? Just above, just below, or in the middle?

Megan Kristel

Thursday 27th of January 2022

A good rule of thumb is either at, or an inch above you knee. You'll want to play with the length against your leg and the kind of heel you'll wear because it really depends on your height and what you are comfortable with. :)