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!

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Ask CF Question

Hi,

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 

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.