Ask CF: How Do I Style a Sheath Dress in a Casual, Edgy Way?

Put a laid-back spin on this workplace staple.

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Woman wearing black sheath dress, maroon coat, and black pointed-toe kitten-heel mules with white bow, and carrying small black leather bag
Modern and chic.

Welcome to the latest edition of Ask CF! Every two weeks, we select a reader fashion question and answer it here on the site. Do you have a specific fashion question for us? Scroll to the bottom of this post to learn how to send it our way!

Ask CF Question


I’ve been following your blog for a few years (university start) and even though I know you get a lot of emails, maybe you will find time to read mine.

The thing is about pencil dresses. I see many of them in stores and am wondering if there’s a way to wear them more “casual” or “rebel” (make them less office-like). I really like those kind of dresses, but I have a problem styling them for everyday. Any ideas?

Kimberly 🙂

Our Response

Dear Kimberly,

I’ll admit that when I got your letter, I knew that fulfilling your request would be hard, because pencil dresses — also known as sheath dresses — have such a strong association with office wear.

However, as I discovered — and hope that you will too — wearing a sheath dress in a casual, and even edgy, way is doable. All you need is a dash of creativity, a willingness to take some fashion risks, and, of course, a few good styling tricks.

So, keep scrolling to see how to style a sheath dress in a casual, edgy way.  (Note: For these looks I used this dress from Nordstrom, but all of them could easily be replicated with almost any simple sheath dress.)

Sheath Dress Outfit #1 

Black sleeveless mock-neck sheath dress with side slit, black leather and suede backpack with bamboo button closure, black off-the-shoulder zip-front sweatshirt, black opaque tights, black knitted sock boots with stiletto heel, gold square stud earrings with faceted pale blue rainbow moonstones, gold hand chain bracelet/adjustable ring with Czech crystal, Cirque Colors nail polish in

Products: Dress – Nordstrom, Backpack – Mango, Sweatshirt – Target, Tights – Topshop, Sock Boots – ASOS, Earrings – Karen London, Hand Chain – Lord & Taylor, Nail Polish – Cirque Colors, Hat – Century 21

For this look, I decided to play with the sheath dress’ mock-neck silhouette by pairing it with a black off-the-shoulder sweatshirt to create an interesting geometric neckline. 

Opaque black tights and heeled black ankle boots keep the look streamlined, and allow the focus to be on the outfit’s shape rather than its color scheme. 

As for jewelry, I chose dainty pieces that have a bit of edge to them, like these moonstone stud earrings, and simple hand chain.

Oxblood nail polish adds a subtle bit of color to the look without being flashy, while a black backpack with a cool bamboo button closure makes for a practical yet stylish accessory.  

An embellished baseball cap adds a touch of lightheartedness to this otherwise-moody ensemble.  

Sheath Dress Outfit #2

Black sleeveless mock-neck sheath dress with side slit, light-wash denim button-up shirt with front chest pockets on either side, lavender kitten-heel pointed-toe mules with fold-over detail, black cat-eye sunglasses with ombré purple lenses, gold multi-layered lariat necklace with clear stone detail and chain fringe, gold open double cuff, gold loop stud earrings, black top-handle bag with cross-body strap, gold hardware, and clear vinyl cover

Products: Dress – Nordstrom, Button-Up – Abercrombie & Fitch, Mules – Mango, Sunglasses – Nordstrom Rack, Necklace – Revolve, Cuff – Lord & Taylor, Earrings – Revolve, Bag – Mango

For a more laid-back look that would work for both school days and weekends, put on a light-wash denim shirt over the shift dress, knotting it at the waist; you could also not wear the shirt at all, and instead tie it around your hips for an effortless look.

These lavender kitten-heel mules have a cool fold-over detail that makes them the perfect shoes to wear with this modern outfit.

Cat-eye sunglasses add a classic touch, but a bag with a clear vinyl cover keeps things current. 

Fun jewelry — a layered lariat necklace, a sleek cuff, and quirky loop earrings — makes for a perfect finishing touch.

Sheath Dress Outfit #3

Black sleeveless mock-neck sheath dress with side slit, black faux-leather motorcycle jacket with silver hardware, Kat Von D Studded Kiss Crème Lipstick in

Products: Dress – Nordstrom, Jacket – Mango, Lipstick – Sephora, Shoes – Topshop, Earrings – Saks Fifth Avenue, Cuff – Shopbop, Bag – Century 21

For the final outfit, I decided to put something together that would be appropriate for a night out.  

A black motorcycle jacket is the perfect layering piece for the sheath dress, while these awesome shoes are a great way to incorporate the Ultra Violet trend into your look. 

A splurge-worthy sliced cuff bracelet takes the ensemble up several notches, while drop earrings that are made to look like the different phases of the moon add a unique touch.  

You can’t go wrong with a quilted cross-body bag to class things up; lastly, a shimmery berry lip color completes the look in an edgy way.

I hope that these looks have inspired you to take sheath dresses from workwear to everyday wear. Thanks for your question!

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What do you think?

Have you ever worn a sheath dress in a casual setting? How did you style it? What do you think of these looks?

Let me know in the comments!

2 thoughts on “Ask CF: How Do I Style a Sheath Dress in a Casual, Edgy Way?”

  1. Aw, I miss the times where you would create four sets, instead of three. It’s probably a lot more work, so I understand, but ugh, you have super great taste. Thanks for your articles, you’re my favorite writer here on CF.


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