This post covers what to wear with a jumper dress over 40 and why every woman should invest a jumper dress. Read how to style a sheath dress for work in midlife, and how to accessorize a jumper dress in multiple, different ways. Get inspired by the outfit inspirations for work and play with this versatile garment.
- You Can Recycle Jumpers in Many Different Work Outfits
- Why to Invest in Jumpers/Sheaths
- How to Accessorize a Jumper Dress in a Different Way
- What Kinds of Bags to Wear with a Jumper Dress?
- What Shoes Go with a Jumper Dress
- Wrapping Up How to Accessorize a Jumper Dress
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You Can Recycle Jumpers in Many Different Work Outfits
In this jumper dress outfit inspiration, I wore my navy blue poplin jumper over a gingham shirt for a work appropriate look. I like jumpers aka sheaths because they provide immediate polish. One can wear them alone or match them with many items like a T-shirts or shirt underneath.


Why to Invest in Jumpers/Sheaths
They can go from casual to work outfit and dinner when you style them with different items and accessories. They also look great with a cardigan, denim or leather jacket for an American Classic Style look or as dress as skirt.
A cropped tweed jacket with a tweed sheath, large gold-colored watch, pearls and medium high block heel court pumps lead to a Euro Chic look – think the young Jackie Kennedy.
How to Accessorize a Jumper Dress in Different Ways
Up your style by using the right accessories. The easiest way to accessorize a jumper dress is a brooch half-way between your neck and widest part of your breast circumference. Try a group of brooches with similar motifs in one look. For instance, several animal brooches or abstract pieces. An odd number is better than pinning an even number of broches or pins.
Use brooches instead of a belt (see first photo). Accessorize with a wood sport watch and a charm bracelet for an alternative on typical Casual Friday outfits.
When the seams of the jumper at your natural waist or the jumper is cut in one piece for the front, accessorize with a belt at your natural waist.

Tip: Switch your classics up with a twist for personal style.
What Shoes Work with a Jumper Dress?
Pumps and Ankle Strap Heels
Pairing a jumper dress with pumps and a bag is a foolproof instant style summer office outfit. However, it can easily go into boredom land when on repeat. Therefore, you want to mix it up to keep it interesting (and to covey the message that you are creative and on top of things).
This gray leather sheath with a striped button-down shirt and gray ankle strap pumps makes for an edgy, but office appropriate look (when HR allows wearing leather). The twist? Wearing leather in spring and summer. It’s perfect on those chilly rainy, windy days. To stay warm in the evening when temperature drops add a white denim jacket or a classic trench coat in a neutral color.


This outfit works because the stripes of the shirt pick up the shades of the different gray of the sheath and shoes and the bag.
Yes, you cane even wear your jumper with sneakers for the weekend, playground, walking the dog and running errands.
In winter, style your jumper with a turtleneck sweater, tights outfits with tall boots or booties.
What Kinds of Bags to Wear with a Jumper Dress?
When you style a work outfit a briefcase, work tote or laptop bag are best. However, large top handle designer bags in a different color than your shoes are great option. The bag and shoes should have the same vibe, but don’t need to have the same color.
When you work in a corporate style work environment in a high ranking position you may even carry expensive luxury bags that read business.
In case you accessorized your jumper for the weekend, playground or farmer’s market an around-town tote or basket work.
Photos: G. Kramm
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