Fall & Winter

How to Wear a Pencil Skirt Over 40: Fit Tips & More

Dear Deborah,

I’ve just returned to work after being at home with my kids for many years, and I’m trying to figure out how to dress. I still have a pretty good body (hourglass shape), and I want to look both businesslike and feminine. I like pencil skirts. Are pencil skirts are still in, and if so, how should I wear one so it fits right and looks fabulous?  Thanks, Jill

 

Tall Boots - Black Pencil Skirt

Hi Jill,

The pencil skirt is a timeless classic that never goes out of style. I think it would be perfect for you because it would highlight your curves, but you’d still look professional. Here are 5 tips for choosing a pencil skirt that fits right and looks Fabulous.

Fall work outfits- Plaid Pencil Skirt

1. Pencil Skirt Fit – Snug but not Tight

Your pencil skirt should be wide enough across your hips to avoid pulling, but it should also be snug enough around your waist to look sleek.  ( You shouldn’t be able to get more than 1 or two fingers between your waist and the waistband)

If you have trouble with the fit, find a pencil skirt that fits your hips and takes the skirt in at the waist, not the other way around. The better the quality, the better the pencil skirt fit.

 

 

Denim Skirts - Denim pencil skirt striped tee

2. Keep your Look Streamlined

Remember, a pencil skirt’s idea is to accentuate those curves, so you don’t want to wear a loose, bulky top or one that’s so long that it covers up half of your skirt. Pencil skirts look best with tops tucked in or that end just at or a bit below the waist.

Bold Stripes - Pencil Skirt

3. A Print Pencil Skirt can look Modern

Pencil skirts in solid black, taupe, navy, or camel are the most appropriate for business, but cute pencil skirts with a pattern are popular. They give off a professional, more creative vibe than a plain-colored pencil skirt.  Wearing one is like saying, “I’m all about business, but I’m not boring!”

4. A Jacket Cranks up Your Authority

A sleeveless blouse can look lovely with a pencil skirt, but at work, it’s always best to have a jacket on hand for those times when you want to show more authority.  A tailored jacket will instantly elevate your credibility and status.

A dark, solid-colored jacket worn with a matching pencil skirt projects a more coordinated look. You’re more likely to see this matched suit combination in high corporate environments, such as law. Coordinated pieces are more suitable in businesses such as communications and sales, as well as in more relaxed corporate environments.

Holiday - Black Lace Pencil Skirt

5. Pencil Skirts Look Fab After Hours Too!

Pencil skirts for work don’t have to be boring. Replace your regular work pump with a stylish shoe featuring ties, ankle straps, and other alluring details, and you can transition your pencil skirt from the boardroom to the bar for after-work drinks and dinner with friends. Or go home, change, and slip on a dressier lace pencil skirt if you are going out to a special event or dinner.

Jill, have a wonderful time back at work, and dress Fab Boss Lady!

Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

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3 thoughts on “How to Wear a Pencil Skirt Over 40: Fit Tips & More

  1. Like the first two, the third one fits poorly even on the model. There is a definite indentation at the lower hip where the skirt is too tight, and you can see how the pocket slits above it bulge out a bit. A good fit is essential with the cut. Otherwise, you look lumpy!

    1. Agree with you there, Kathy. They didn’t have the right size for the model and squeezed her in. Thanks for pointing that out. Deborah