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In Praise of Pencil Skirts – Why They’re Awesome & What To Wear With Them

October 17, 2020

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I’m going to go out on a tree branch and say… when it comes to workwear, pencil skirts are one of the most versatile, chic, and timeless items you can have in your closet.

Versatile? Because they are always stylish and appropriate. Not to mention, they make the day into night transition look easy peasy. Cocktails after work anyone?

Timeless? Because while lengths may vary slightly season to season, the slim silhouette remains much the same.

So once we own a few of these classic little gems, we face the challenge of what to pair with them that’ll fit & flatter your body and mesh with your style.

But that’s a challenge no longer, Sunshine! Here are 13, yes, 13 fabulous tops that’ll look smashing on you this fall.

But, before we dive in we must briefly talk proportion.

The 66/33 Rule:

13 Perfect Tops For Pencil Skirts

I hate rules and love breaking them. However… to quote an old cliché, adage, manifesto, whatever, we need to know the rules before we break them.

So here it is. I like to call this the 66/33 rule. Sort of like 80/20 but different.

I’m super excited to share this because once you know it you’ll suddenly and immediately understand why some outfits just seem to magically work while others just seem… off.

Even better, from now on, you’ll see proportions that are out of whack and know why. And more exciting, you’ll know how to fix it.

A picture is worth a bazillion words, so when it comes to proportion the goal is to have 66% of your length come from your waist down and the 33% to come from your waist up.

Pretty simple, right?

In Case You’re Asking, Where’s My Waist?

The easiest way to tell is to bend your arms and then put your elbow against your side. That’s it.

Now, your actual waist might fall higher or lower – hence all the chitter-chatter about long, short, or high waisted. But wherever your elbow hits is where we want to create the illusion that your actual waist is.

A Couple Things You’ll Likely Notice:

All these tops all hit at the hip bone or above. Not to bang away more on proportions, but because of the length of pencil skirts, the most flattering tops will be on the short side.

Something else that most of these tops have in common is either a very definitive waistline or created from a softer material that allows you to belt it without any additional bulk.

One more thing… the top options are divided into conservative or creative. So, if you fall firmly into one camp versus the other, you can scroll right to that area.

Now that that’s out of the way, let’s dive into some fun Fall tops that’ll turn that classic pencil skirt into an exciting and super flattering fall office outfit.

For Classy, Conservative Girls:

13 Perfect Tops For Pencil Skirts

The Marc Jacobs Pearl Trim Leotard $395. Tap The Picture For More Details.

Bodysuits almost completely eradicate panty lines which make them brilliant for slim fitting pencil skirts. So brilliant in fact, I’m including the next one too!

13 Perfect Tops For Pencil Skirts

Vince Long Sleeve Crossover Bodysuit $165. Tap The Picture For More Info.

13 Perfect Tops For Pencil Skirts

Ann Taylor Floral Mixed Media Tie Waist Shell
$54.50. Tap The Pic For More Info.

This shell will work perfect under almost any jacket and the front tie is going your waist look amazing!

13 Perfect Tops For Pencil Skirts

I like this peplum blouse because of its softer/less dramatic lines that give it a more modern feel.

13 Perfect Tops For Pencil Skirts

CECE Pleat Sleeve Collared Crepe Blouse $79. Tap The Picture For More Details.

I debated about which category to put this under; creative or conservative, because honestly depending on your accessories it could go either way. If your style is edgier, I can totally picture this with a badass pair of biker boots or patent leather Mary Janes. But that’s beauty of this versatile blouse. Either way you take it – enjoy!

13 Perfect Tops For Pencil Skirts

J. Crew
Collection silk twill top with fixed bow $138. Tap the picture for all the options.

This bowed gem also comes in a lavender/navy (which I’m obsessed with) and a red/pink combo. Also, when I wrote this article it’s 40% off, but I’m not sure how long the sale will last.

13 Perfect Tops For Pencil Skirts

Banana Republic Pleated Shirt $62. Tap The Picture For More Info.

The lightweight material makes this one a perfect top for transitioning from summer into fall.

Have Fun Creative Girls! These Tops Are For You:

13 Perfect Tops For Pencil Skirts

Are those puff sleeves bonkers or what?!? If you love them as much as I do, make sure to check out the article all about Ruffles, Bows, & Puffs here.

13 Perfect Tops For Pencil Skirts

Asos Monki Maya shirred cotton blouse $48. Tap The Picture For More Details.

This blouse has found the perfect balance between covered up yet flattering. Brilliant!

13 Perfect Tops For Pencil Skirts

Staud Luna Top $315. Tap The Picture For All The Info.

This vegan leather number is screaming out for a short scarf or layered necklaces or both. The accessories options are limit-less.

13 Perfect Tops For Pencil Skirts

Free People Fall for You Twisted Top $78. Tap The Pic For More Info.

This also comes is a warm cream. And if you’re thinking, Gadzooks Batman! I can’t flash my stomach at work! No worries – a contrasting cami underneath is always a fun option.

13 Perfect Tops For Pencil Skirts

Ba&sh Hippie Top $245. You Know The Drill – Tap The Pic For More Info.

Here they let the bow legs hang, but I think it would be super cute tied into a big-ole bow.

13 Perfect Tops For Pencil Skirts

Anthropologie Joanna Ruffled Top $68. Tap The Picture For More Details.

A top so simple, yet so many charming details; the ruffles on the shoulders, the flattering pleats on the front, and finally, the front panel. Added Bonus – If you’re like me and have stomach-showing issues, the front panel is going to do an amazing job camouflaging.

That’s A Wrap, Sunshine!

Although I have about six more perfect tops for pencil skirts that I’m dying to show you, I’m going to stop it now. After all, you are a busy woman and have other things to do than on-line shop at 5 o’clock in the morning :-).

But… if you have a moment, leave a comment below. Do you love pencil skirts? Excited about picking up some new fall blouses? Fill me in and we’ll get the conversation started.

‘Til Next Week.

Hugs & Happy Shopping.

Our Style Addiction - Angela

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13 Perfect Tops For Pencil Skirts

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