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One of the most versatile pieces you can add to your wardrobe are jumper dresses. There are many more ways of wearing it than in the classic sheath under sweater combination shown in the Mad Men TV series. In this guide, you learn how to wear your sheath as a skirt and in multiple other ways year round. Read to create more looks with the pieces you own for more sustainable fashion.


  1. Sheath Dresses Are Versatile to Style
  2. Sheath Dress Outfit Ideas
  3. Sheath Dress as a Skirt
  4. Same Style Recipe, Different Color, New Look
  5. A Leather Sheath Can Be Styled for the Office
  6. Wear Your Jumper with a Blazer
  7. How to Style a Plaid Sheath Dress
  8. Don’t Underestimate the Power of Accessories
  9. Sheath as Skirt in a Nutshell


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Sheath Dresses Are Versatile to Style

Well, it’s because they have no sleeves or just short sleeves like cap sleeves or 3/4 sleeves. They look great just on their own. A sheath dress is an instant outfit with a pair of pumps. It’s a no-brainer to wear them with something underneath, at least in the cold season. You can even create an outfit for St. Patrick’s Day by adding a green sweater, shirt or cardigan.


Sheath Dress Outfit Ideas

Here some ideas how not to get into a style rut and how not to look boring or get bored over time. In fall, a jumper looks great with a blouse/shirt underneath or worn over the sheath. In winter, you may wear a turtleneck cashmere sweater underneath, and even add a blazer for those 40 below zero days. A motor cycle jacket pulls a sheath into the cool territory for a girls’ night out on the town. A denim jacket shifts the sheath to casual territory for a Sunday brunch. It looks office appropriate with a pair of pumps and a blazer or cardigan. A sheath dress is really worth its money. Read on to get inspired and learn about even more options.

Sheaths are the champions in being able to create multiple looks with the same item.



Sheath Dress as a Skirt

In fall, use blazers instead of a coat because it will helps you to not get bored of your outerwear already early in winter. In regions with long winters, try to wear various pieces in quite different ways, and to incorporate pieces from summer in your summer-to-fall transition outfits.


leather sheath as skirt with denim shirt worn over it
Example shirt over sheath



fashion blogger over 50 in a sheath leather dress as skirt for the office
Outfit details: Unbranded leather sheath dress, Great Northwest denim shirt, Burberry plaid blazer, pearls, Kieselstein Cord belt and buckle, Kate Moss for Longchamp bag, and Anne Klein T-strap pumps (all own)


An Easy Way to Create a Separates Look with a Sheath

The following outfit idea features a sheath dress worn as skirt. In this inspiration, the colors make the look work. The argyle pattern has purple, grey, and burgundy colors, which seem to scream for my patent leather burgundy ankle strap pumps and my lilac Coach bag. The lilac stays in the color families of the sweater’s pattern as it seems to be a mix of grey and purple. To finish the outfit I added a long pendent necklace.



woman wearing a argyle sweater over a sheath dress
Outfit details: L.L. Bean argyle sweater,Elli Tahari sheath dress, Steven Mary Janes, Hermes collier de chien bangle, statement necklace, and Coach bag


#maturefashion woman in a dress that features the colors of the aurora
Sweater over sheath. Pin it to look like a half tuck


sheath dress worn as skirt
BB Dakota floral sheath worn under Ann Taylor dyed sweater with GNW tight, Seiko watch,  smoky quartz statement necklace, and Aldo pumps


In the following example, a Fair Isle sweater makes a beautiful winter separates look with my second hand hounds-tooth patterned dress.

Look at a dress as a skirt or even top to get more outfits out of your wardrobe. #budgetfashion Click To Tweet
style book author in houndstooth sheath with Fair Isle sweater
Fair Isle Eddie Bauer sweater, hounds tooth Loft sheath dress, opera length pearl necklace, Paloma Picasso sunglasses, Celine bag, GNW tights and pumps


The example below works with the same principle, but turns a leather jumper into a skirt under an Irish cable-knit Sweater.

fashion over 50 back view of a winter work outfit with sheath as a skirt
Back view
belt buckle
Buckle details


Details of printed pantyhose

fashion blogger over 40 donning an Alaskan winter outfit with sheath as a skirt under an Irish cable-knit sweater


Same Style Recipe, Different Color Scheme, New Look

The following two work outfits both base on the same styling recipe: Dress with knit jacket, tights and booties. Nevertheless, these two work outfits look quite different from each other due to the change in the color scheme. Who says that instant style would lead to boring outfits over time? On the contrary, it can make up your signature style!

Make a styling recipe your signature style. #personalstyle Click To Tweet

The work outfit shown below has a burgundy jacket and burgundy tights. The accessories, a square silk scarf worn as arm candy and wood watch stay with the burgundy theme. The color combination works two basic colors red and blue darkened with black to burgundy and navy. It also would work with the black and white extreme with the white in the tweed and the black booties.


over 50 years old fashion blogger in Shein navy and white pencil dress with burgundy accents
Chanel-inpired sheath

style book author in sheath with cardigan and booties


Stylist’s secret: Change the vibe of the look with your color choice


The next outfit uses blue and green, which are adjacent colors. You can add brown as a neutral for balance. This outfit has a calming vibe, while the first outfit has a more powerful attitude.


mature fashion blogger in work outfit with Shein sheath and cardigan
GNW teal knit jacket and tight, Antonio Melani booties, Sak bag, Festina watch, jade best girlfriend bracelet c/o Chico’s, and sheath dress c/o Shein


Don’t forget to add at least one trendy item to look great in tweed over 40, no matter whether the tweed clothing is a sheath, (styled as) skirt or blazer.


A Leather Sheath Can Be Styled for the Office

Leather sheaths are often considered as party dresses. However, when you buy one in around the knee length, you can wear them in your everyday life. You can even style them like a normal solid color jumper for the office when your work dress  code allows leather.

Stylist tip: It’s easier when the leather isn’t shiny or black.


older woman in leather jumper with blazer
Jones New York Hawaiian print shirt, Elie Tahari leather sheat dress, Burberry plaid blazer, plateau loafers and 3.1 Philip Lim fuchsia bag (all own)


Wear Your Jumper with a Blazer

Paired with a blazer a solid color sheath looks always office appropriate. It’s a perfect look for a business casual work environment when meeting customers or for a meeting.

posh chic look with sheath dress and blazer
White jumper with belted plaid blazer



mature woman in gold leather trench coat
Outfit details:  Burberry trench coat, Burberry plaid blazer, Jaeger tote, Anne Klein pumps, Ray Ban sunglasses, and winter-white V-neck dress c/o Lookbook Store



How to Style a Plaid Sheath Dress

It’s a no-brainer to pick up the colors of the plaid pattern (next photo). Why not going for an unexpected look with a pop of color like in the second next photo? Not so brave?


plaid sheath jumper office outfit
Ann Taylor cashmere sweater, Ruby Belle plaid sheath dress, Hermes bracelets, and Harley Davidson booties


jumper with denim jacket and leather vest
Ruby Belle sheath, oversize Great Northwest denim jacket, Moda International leather motorcycle vest, necklace, opaque GNW tights, and Harley Davidson booties


A sheath dress can go from sophisticated to girly, to street style.



Don’t Underestimate the Power of Accessories

There is this saying

A pair of shoes can make or break the look.

Use your footwear as to vary your look. For example, think about the difference a pair of pumps with pantyhose makes vs. tall boots with opaque black tights.

Don’t forget to accessorize. Read how to change a good look to an awesome one with brooches.


accessories Arm party
Arm party: Golden bangle (gift from my late mother), enamel bangle (gift from my girl friend), Hermes enamel lion bangle, and Tissot stone watch


Wearing a sheath as skirt with a bulky sweater can look frumpy. Therefore, accentuate your waist with a belt for shape.  Also, try altering the vibe of your jumper with a belt. More on how to best accessorize with belts.


Sheath Dress as Skirt in a Nutshell

Using style recipes like presented here is an easy way to achieve ageless style. They also help you to get more outfits from your wardrobe. Moreover, style recipes take the stress out of getting dressed. My style recipe book How to Dress for Success in Midlife has timeless, easy-to-follow outfit suggestions for all kind of dressing situations in midlife. Buy the book now.

More outfit ideas for a sheath dress.


Photos: G. Kramm, N. Mölders

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