What to Wear with a Pencil Skirt? Find out Here!!


Are you looking for what to wear with a pencil skirt? 

So was I! 

And the thing about it is the skirt itself is a winner!  But finding something to wear with it that creates a great look is a whole other ball of wax. 

I went through the agony of wearing my skirt with tops that did nothing at all for the look I was going for. 

Yes, there are photos out there of what to wear, and either trying to copy the idea didn’t look as good on me or I just couldn’t find the complementary pieces of what I saw in the photo. 

So what to do right??!! 


I finally figured it out so wanted to share my lightbulb moment with you to help you figure out what looks best on you to wear with your pencil skirt. 

Let’s get this out of the way first thing:  You want to start with a skirt that fits you and fits you well. 

You want the cut to be a compliment not too tight and not too loose, yes it matters, the fit is everything. 

So start with a great fitting skirt (if you’re still looking just check out the skirt below and know it is highly recommended due to the cut).

For now, I’ll assume you have a pencil skirt and if you’re still on the hunt, just check out our pick.  


So the thing you need to do first is decide what look you’re going for.  That’s important groundwork. 

If the look is formal these are the things that matter:  Wearing a loose fitting flowy top that falls at mid hip creates a great look to your outfit, try this look with a pair of pumps.

I prefer at least a 3 inch heel but whatever you are comfortable with.

It doesn’t matter if it has sleeves or not, all those little things should be left for you to decide what looks best on you.

It’s great to see a visual of what something looks like on someone else but it is a skill to learn how to visualize something on you as well as how to put it together. 

Once you master this skill it will become second nature.


Hopefully, you can paint a mental picture of seeing yourself in the outfit I’m laying out.

It will give you a new way of thinking and can change the way you shop and make your outfits enhance your figure and give you the look you’ve been trying to master.

With remote work becoming a new normal there is still a need to meet with clients and sometimes attend an important meeting.  

There will always be a need to dress up and put on your Corporate Look every once in a while so why not do it with a little style. 

Check out the Forbes Article on Business Casual here.

This post contains affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through a link.

Enough with the prelims, let’s get on to the tops you can wear with a pencil skirt:


This Swing top is a high fashion statement and has it all, comfort, style and it offers a great silhouette when worn with a pencil skirt and pumps.

#2  COTTON Cardigan – ANGIE + WES


Every Wardrobe needs a button up Cotton Cardigan!  Yes, EVERY WARDROBE!  It is one of those staples that help you to change up your look and can be worn with a pencil skirt to create a polished look.  Pair it with the matching top.

#3 Stunning White Blouse


This top is minimalist with an edge.   Wear with your pencil skirt with heels and this will be a great look for any Corporate Event.


The Straight Pencil Skirt made by Susanna Monaco and sold at Shopbop will always be a staple that adds a sense of style to your wardrobe.  It’s a timeless skirt that speaks for itself and looks amazing.  You can dress this up or down. 


What to Wear with a Pencil Skirt

This Swing top (currently available only in Lt Grey) is a high fashion statement and has it all, comfort, style and it offers a great silhouette when worn with a pencil skirt and pumps.


What to Wear with a Pencil Skirt

This is the pencil skirt we can stand behind.  The fit says it all. This skirt is a pull on knit and exudes comfort needing no zipper.  It’s not easy to find a pencil skirt that offers old world charm and modern lines but this skirt does that.  Also, as with most ANGIE + WES pieces, it’s easy care and no need for the dry cleaners.


These are the tops that can successfully be worn with pencil skirts.  They all answer the questions of ‘What to Wear With a Pencil Skirt.’

What you wear does matter.  If comfort and style is important to you, choosing one of these styles should make you very happy. 

Also, it’s so important to keep your wardrobe updated.  If you believe in continuous improvement, you may want to keep your resume dusted off and ready to go. 

Leave some room for interviews, whether they are inside or outside of your current employer. 

This Forbes Article can be helpful in preparing you to raise the bar for your career and provide some guidance on what you can wear. 

We hope you enjoyed this post.  We are always working to add value to the working woman and the woman on the go. 

You’re valuable and have so much to give, why not look amazing while living your best life?  

To stay updated on future posts, sign up for our email list and we will keep you posted on great finds that can help you find what you can wear. 

We will keep you up to date and promise not to clog up your mailbox…

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