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One of the most versatile pieces you can add to your wardrobe are jumper dresses. In this post, you learn how to wear your sheath multiple different ways yearround.

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

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Sheath Dresses Are Versatile to Style

Sheath dresses are very versatile. 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 when putting on a pair of pumps. It’s a no-brainer to wear them with something underneath, at least in the cold season. You can wear it in various combination like with a green sweater as an outfit for St. Patrick’s Day.

Nevertheless, sometimes it may be stressful to come up with ideas to not look the same, same.

But you love this dress, right?

There are many more ways of wearing it than the classic sheath under sweater combination that became famous with the Mad Men TV series.

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.

fashion blogger in plaid sheath, red cardigan and tights
Dyed Moda International cardigan, GNW tights, Hermes collier de chien bangle, Clark booties (all own)

Sheath Dress Styling for Fall

In fall, use blazers as a jacket when the temperatures allow for it. Doing so helps you to not get bored of your wardrobe when you have to wear winter clothes for up to seven month (e.g. northern Europe and Canada, Russia, Alaska). In regions with long winters, try to wear various pieces in quite different ways, and to incorporate pieces from summer.


leather sheath as skirt with denim shirt worn over it

styling a dress with a shirt for a separates look

fashion blogger over 50 in a 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.


stylist with sweater over jumper

woman wearing a argyle sweater over a sheath dress
Outfit details: L.L. bean argyle sweater worn over Elli Tahari sheath dress with Steven Mary Janes, Hermes collier de chien bangle, statement necklace, and Coach bag (all own) for a modern way to wear the Mod argyle


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 worn over a hounds tooth Loft sheath dress accessorized with opera length pearl necklace, Paloma Picasso sunglasses, Celine bag, GNW tights and pumps (all own)


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

belt buckle


fashion blogger over 40 donning an Alaskan winter outfit with Irish cable-knit sweater
Winter outfit with Orvis Irish cable-knit sweater, Eli Tahari leather dress, Kieselstein Cord belt and buckle, GNW tight, Söft shearling booties and Festina watch (all own)

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. These two posh office outfits, however, 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

style book author in sheath with cardigan and booties
Outfit details of winter work outfit: Chanel-inspired tweed sheath dress c/o Shein styled with own GNW burgundy cardigan, burgundy and blue neckerchief worn as bracelet, GNW burgundy tight, garnet necklace and earrings (all own), wood watch c/o Jord, and Mousse & Cloud booties c/o Coolway


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

The next outfit works with neighboring colors on the color wheel, blue and green and the shades thereof. You can add brown as a neutral for balance. This outfit has a calming vibe, while the first outfit has a more powerful attitude. In case you missed it, you can find the review of this tweed sheath at the link.

Don’t let the right outfit be a random thing. Wear the right look in every situation by looking up easy to follow styling recipes in How to Dress for Success in Midlife. Buy my book now.


mature style winter work outfit with cardigan and tweed dress

mature fashion blogger in work outfit with Shein sheath and cardigan
GNW teal knit jacket, teal GNW tight, Antonio Melani booties, Sak bag, Festina watch (all own), 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 they are not super short, you can get more wear out of them. Just style them like a normal solid color jumper for the office.

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

midlife woman in work outfit

mature woman in gold leather trench coat
Golden leather Burberry trench coat with Burberry plaid blazer, Jaeger tote, Anne Klein pumps, Ray Ban sunglasses (all own) 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
Ruby Belle plaid sheath dress, Ann Taylor cashmere sweater, Hermes bracelets, and Harley Davidson booties


stylist in white winter outfit
Ruby Belle plaid sheath dress, Paloma Picasso sunglasses, Hermes collier de chien bangle, Hermes Medor watch with green wrist band, GNW tight, HH-booties, and chartreuse Landsend cashmere sweater (all own)


jumper with denim jacket and leather vest
Ruby Belle plaid sheath dress worn as skirt under an oversize Great Northwest denim jacket with leather motorcycle vest, flower and multiple strings of beads statement necklace, opaque GNW tights, and Harley Davidson motorcycle booties (all own)


A sheath dress can go from sophisticated to girly, to street style. #styling Click To Tweet

Don’t Underestimate the Power of Accessories

There is this saying

A pair of shoes can make or break the look. #fashionquote #agelesstyle Click To Tweet

While there is a lot of truth to this fashion quote, the footwear is also an opportunity. Just think about what a difference a pair of pumps with pantyhose make vs. opaque black tights and boots.

Don’t forget what you have in your jewelry box. Brooches are great ways to add an acsent to a look. Learn 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 (all own)


Belts are another great option to alter the vibe of a sheath. Learn how to best accessorize with belts to create more looks with the pieces you own.

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.

When you liked this post, please recommend the post to your friends. I just read a cool post on creating outfits using style recipes. #easystyle #agelessstyle Click To Tweet

How do you style your sheath? Do you use “styling recipes”? Do you think about your color combinations and what vibe they convey? What are your work outfit challenges? Do you have a favorite sheath that you wear again and again? Do you wear it always the same way or differently? What is your favorite dress? Let me know, so I can help you.

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Do you style your outerwear? Just curious.

Photos: G. Kramm, N. Mölders

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