1 Pencil Skirt 5 Ways

I’ve had many requests to see pencil skirts styled multiple ways over the last few months – and it’s been a request that has taken me longer to fulfill. Don’t get me wrong, I love pencil skirts, but finding one that actually fits me, is another thing. Pencil skirts are typically too tight in my hips and too loose in my waist, and I’ve yet to find a pencil skirt that’s made for a curvier frame.

I’ve ordered a few to try and have sent many back, but this one in particular is finally a good fit. I went up one size in this skirt to accomodate my hips, and the waist isn’t a perfect fit, but it’s not crazy oversized – so I think it’s a win. Plus, the print is really cute!

So, I’m finally able to deliver on a pencil skirt styled multiple ways style session, and I hope it gives you a little inspiration!

1 Pencil Skirt 5 Ways

My Sizing: I’ve had requests for my height and measurements to assist you with choosing the right size when you shop my posts, so I’ll be including this on every post. I’m 4’10”, and around 105lbs. My bust, waist and hip measurements are 32″, 24″, and 36″.

Casual Side

I typically think of a pencil skirt as something to wear to work, but they can be dressed down too, especially a nice cotton one with a fun print. So, I added my favorite sandals and knotted my tank top for a casual vibe. Although it’s a little dressed down, I could personally still wear this look to work.

Five ways to wear a pencil skirt | petite pencil skirt
Sizing: Skirt Petite 0 | Top XXS | Jacket Petite XS | Shoes Size 5 TTS
Casual way to wear a pencil skirt | Pencil skirt outfits via pumps and push-ups blog | petite style blog
Sizing: Skirt Petite 0 | Top XXS | Jacket Petite XS | Shoes Size 5 TTS

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With a Blazer

Nothing says business casual like a blazer and a pencil skirt. This skirt has a cream undertone that I didn’t love paired with my white blazer, but this pink one is a pretty neutral that I think looks great with the tan sweater tank top. I didn’t photograph it, but I think the tank top looks just fine without the blazer too. My exact blazer is sold out, but I’m linking a blazer with a similar fit.

Five ways to wear a pencil skirt via petite style blog pumps and push-ups | petite style blogger | petite style
Sizing: Skirt Petite 0 | Top Petite XXS | Jacket Petite 00 | Shoes Size 5 TTS

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With a Sleeveless Blouse

Pencil skirts always look nice with a pretty blouse. I chose a sleeveless one for the season.

Summer pencil skirt outfits via pumps and push-ups blog | petite style blogger | petite style blog
Sizing: Skirt Petite 0 | Top Petite XXS | Shoes 4.5 Size down 1/2 size

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With a Chambray Top

If you don’t have a chambray top – get one! The most versatile top I have in my closet, that goes with everything! You can tuck the top in for a more professional look, but I like it knotted to look a little more casual with my flats.

Pencil skirt outfits for petite women | petite style | petite summer outfits | business casual outfits
Sizing: Skirt Petite 0 | Top Petite XS | Shoes 5 TTS

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With a Dressed Up T-Shirt

I know ruffles aren’t for everyone, but whenever I comes across a simple t-shirt with ruffles, I can’t help but buy it. I think the ruffles instantly dress up an otherwise basic top and it’s really comfortable! This top in particular is a linen blend.

Summer business casual outfits | petite style blogger | petite style blog
Sizing: Skirt Petite 0 | Top XXS | Shoes 5 TTS

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Pencil Skirts

I would like to say that all No. 2 pencil skirts from J.Crew fit like this one, but they don’t. I do love J.Crew, but the sizing is not always consistent and for me, this particular skirt fit better than the solid No. 2 pencil skirt.

I know many people are still working from home (and I’ve seen your requests too). I’ve been back at the office for a few months now, living that mask life. What about you, are you still WFH or back at the office?

-Brooke

Brooke of Pumps and Push-Ups - petite style blogger

Hello, I'm Brooke!

A petite (4'10") gal on the hunt for the best petite clothes. I show you where to shop for petite finds, and how to style them in my weekly style sessions. I don't alter or hem any of the clothing on my blog - what you see is exactly how the items fit me right from the store.

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Pumps and Push-Ups participates in affiliate programs, including Rewardstyle and the Amazon Associates Progam. Pumps and Push-Ups earns commissions from qualifying purchases made through links posted.