If you’re looking for a skirt to wear for work or for an evening out, you really can’t go wrong with a pencil skirt. But what top should you wear with it? Below I explore the best tops to wear with pencil skirts with 9 pencil skirt outfits for you.

Who suits a pencil skirt?

First, does a pencil skirt flatter everyone? Well, that depends how you wear it.

A pencil skirt is perfect for the hourglass as it flatters your natural waist and curves.

For the pear, you could wear a dark pencil skirt and lighter top if you like to downplay your hips. Of course you can also embrace your pear shape and accentuate your wider hips by doing the opposite.

If you are an inverted triangle, you can do the opposite from a pear and wear a lighter colored pencil skirt to downplay your bigger upper body.

If you’re a rectangle, it will emphasize your athletic figure. If you want to create more curves, you could wear a peplum or wrap top.

For the apple shaped body, a wrap top, drape top or jacket will help to disguise a belly.

Now, let’s look at some outfits featuring pencil skirts.

1. Tucked in shirt

Pencil skirt outfits - Natalia in an all-blue outfit | 40plusstyle.com

Natalia @odin.stylish.me above opts for an on-trend outfit in one color. This is a great way to wear your pencil skirt if you want it to look more like a dress.

Recreate her outfit with this similar top, midi skirt, sandals, handbag, necklace and sunglasses.

Of course this look also really works with contrasting color combinations as seen in the outfit below.

Shirt and pencil skirt outfit | 40plusstyle.com

L’AGENCE Holly Stripe Long Sleeve Button-Up ShirtBelle Poque Midi Pencil SkirtNUBILY Laptop Tote BagNaturalizer Samantha Pointed Toe FlatMadewell Freshwater Coin Pearl Huggie Hoop Earrings

2. A peplum top

Peplum tops work particularly well with pencil skirts because they match each other in sophistication. A peplum can create or emphasize curves. Plus, as you don’t tuck this type of top in, it can help to hide a little bit of a tummy.

Peplum top and pencil skirt outfit | 40plusstyle.com

GRACE KARIN Wrap Peplum TopGRACE KARIN Pencil SkirtClarks Linvale Jerica PumpKate Spade New York Penny Pebbled Leather Shoulder BagMadewell Freshwater Coin Pearl Huggie Hoop Earrings

3. Pussy bow blouse

A pencil skirt and pussy bow blouse create a vintage, 1950s style look which is perfect for the office or an evening out.

Pussy bow blouse outfit | 40plusstyle.com

Cinq á Sept Khloe Ruched Sleeve BlazerBelle Poque Bow Tie BlouseHybrid & Company Ponte Pencil SkirtDREAM PAIRS Mary Jane PumpAimee Kestenberg Busy Bee Leather SatchelKate Spade New York Mini Small Square Huggies Earrings

4. sweater

Patricia in a sweater and green skirt | 40plusstyle.com

Patricia @madamechicbcn above (read her style interview here) wears a classic beige sweater with her green midi pencil skirt.

Steal her look with this similar sweater, skirt (plus size option here), pumps, bag, earrings and sunglasses.

You could also choose an off-the-shoulder sweater like the outfit below.

Off the shoulder sweater and skirt outfit | 40plusstyle.com

Simlu Off The Shoulder TopBelle Poque Ruched Pencil SkirtNaturalizer Samantha Pointed Toe FlatAimee Kestenberg Busy Bee Leather SatchelKate Spade New York Mini Small Square Huggies Earrings

5. t-shirt

While pencil skirts are associated with professional and formal looks, you can also wear yours more casually. Wear with a t-shirt and sweaters for everyday.

t-shirt and skirt outfit | 40plusstyle.com

Nordstrom Crewneck T-ShirtKate Kasin Wrap Pencil SkirtSperry Crest Vibe SneakerAimee Kestenberg Busy Bee Leather SatchelKate Spade New York Mini Small Square Huggies Earrings

6. wrap top

If you don’t want to tuck your top into your pencil skirt, a wrap top will work well. This will add shape to your figure and is also perfect for hiding a belly or muffin top.

Wrap top and skirt outfit | 40plusstyle.com

Halogen Belted Wool Blend CoatAnne Klein Geo Print Wrap TopGRACE KARIN Pencil SkirtAllegra K Chunky Heel Knee High BootsNUBILY Laptop Tote BagKate Spade New York Mini Small Square Huggies Earrings

7. sleeveless top and blazer

Tanasha wears a red pencil skirt | 40plusstyle.com

Tanasha @prettytallstyle above chooses a classic look with a pencil skirt and blazer. See how she switches her shoe choice to create a slightly different look.

Check out this similar top, blazer, ruched skirt, pumps (black option), bag, earrings and belt.

Print pencil skirt outfit | 40plusstyle.com

FASHIONOLIC Gathered Sleeve Open BlazerKOBI HALPERIN Leyla Sleeveless Chiffon BlouseRANPHEE Ruched Wrap Pencil SkirtSARTO by Franco Sarto Devin Pointed Toe Slingback Pumprag & bone Field Leather ClutchKate Spade New York That Sparkle Round Stud Earrings

8. Tunic top

Another option for you if you want to wear your top outside of your skirt, perhaps because you have an apple-shaped figure or want to hide a belly. Choosing asymmetry in your top means you won’t look as if you have visually cut your body into two halves with your clothes, which generally isn’t flattering.

Tunic and skirt outfit | 40plusstyle.com

Esenchel Tunic TopKate Kasin Pencil SkirtChinese Laundry Carlita Ankle BootKarine Sultan Layered Imitation Pearl Pendant NecklaceAimee Kestenberg Busy Bee Leather SatchelMadewell Freshwater Coin Pearl Huggie Hoop Earrings

9. high neck top

For a sophisticated look, you could choose a high neck top with your pencil skirt. The look below would work well for a dinner out.

High neck top and skirt outfit | 40plusstyle.com

Karen Millen Italian Premium Check Belted Trench CoatMisook Cowl Neck Sleeveless BlouseKate Kasin Bow Tie Pencil SkirtSARTO by Franco Sarto Devin Pointed Toe Slingback Pumprag & bone Field Leather ClutchKate Spade New York That Sparkle Round Stud Earrings

More pencil skirt outfits inspiration

Below, you can see more outfit ideas starting with a pencil skirt.

Tops for pencil skirt outfits: the best tops to wear with your classic pencil skirt | 40plusstyle.com

Karen @styledbykaren above shows how you could wear your pencil skirt for summer.

Recreate her outfit with this similar silk top (another option here), skirt, sandals, watch and sunglasses.

Kim in a sequin skirt and moto jacket | 40plusstyle.com

Kim @kimair (read her style interview here) opts for a glamour look with a sequin pencil skirt and studded moto jacket, teamed with white shoes.

Check out these moto jackets from Amazon, Sam Edelman, BLANKNYC and Levi’s that you can wear with this similar top, skirt and pumps.

White shirt and pink skirt outfit | 40plusstyle.com

Julie @stylishparadox above (read her style interview here) shows how you could wear a white shirt over your pencil skirt.

Get her look with this similar shirt, skirt, sandals, clutch, necklace (another option here) and earrings.

Pencil skirt outfits together in one capsule

Below, you can see all of the pencil skirt outfits from above together in one capsule. You can easily wear any of the tops with any of the skirts.

Pencil skirt outfits | 40plusstyle.com

shop some of the pencil skirt outfits above here:

Continue reading:

  1. The Best Tops To Hide Your Tummy
  2. The Best Pants And Skirts To Fit And Hide Your Belly
  3. What To Wear With A Black Skirt: 9 Black Skirt Outfits To Inspire You

Like this article on tops for pencil skirt outfits? Share it on Pinterest

Tops for pencil skirt outfits: the best tops to wear with your classic pencil skirt | 40plusstyle.com

Feature image by Kim @kimair

Sylvia

Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

Want to get more articles from 40+style in your inbox, subscribe here.

You can also connect with 40+style on Facebook, Instagram or Pinterest.

Support 40+style by using the links in our articles to shop. As an associate for Amazon and many other brands, we receive a small commission (at no cost to you) on qualifying purchases which enables us to keep creating amazing free content for you. Thanks!