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Wiggle Dress Pencil Skirt – Vintage Office Wear Fashion

How to wear vintage to the office: the wiggle dress, the pencil skirt, 1950s suits and blouses, and eight tips for keeping it smart at work.

Four wiggle dresses from Mad Men: a blue shirtdress, a black satin dress, a fuchsia sheath and a green satin dress

With Mad Men, Downton Abbey and The Great Gatsby guiding modern fashion trends, vintage-inspired fashion is on the rise. Now, you might think you can’t wear vintage to the office, that it is only for after hours and weekends, but we think you might be wrong. Vintage is becoming more acceptable at work, especially in creative industries like graphic design, digital media, publishing, tech, advertising and non-profit, and in other less formal offices. If you work for a bank, a law firm or an insurance company, it might be a little more difficult to fit your vintage looks into the formal office dress code. But don’t be afraid to experiment a little and throw in a vintage piece here and there.

Mad Men costumes side by side: a belted blue dress, black satin, a pink sheath and a green draped dress

Still: Mad Men, AMC

A good place to start figuring out what vintage looks to wear to the office is to look at women’s office wear of the past.

Leather pencil skirts

Queen Letizia of Spain always rocks a red leather pencil skirt. She is a big fan of the Inditex fashion label Uterqüe.

Meghan Markle wears one too.

Meghan Markle in a burgundy knit top and red leather pencil skirt, smiling and talking with a man in a blue suit
Queen Letizia and Meghan Markle side by side in red leather pencil skirts, one with a white blouse, one with a burgundy top

In fact, I have the same red leather pencil skirt from Uterqüe too.

Gracie Opulanza seated on a blue velvet sofa in a red leather pencil skirt, black ruffled-sleeve top and blue slippers

Mine is the same red leather. But it has a split and a matching belt.

It looks wonderful with a black opulent T-shirt with sparkle.

Gracie Opulanza taking a mirror selfie in a red leather pencil skirt and black sparkly top

Don’t forget to add accessories. A pencil skirt is fabulous when turning fifty.

The wiggle dress

Our first and favourite option: the wiggle dress. If you have never heard of it, think of Joan Holloway, later Joan Harris, from Mad Men, above. During the 1950s and 1960s women wore wiggle dresses to the office. They were very body-conscious, and meant to exaggerate the hourglass silhouette, with a hemline that narrowed from the hips to the knee.

Black pencil dress with a rust and black chevron-striped bodice on a dress form, beside the same dress in Mad Men

Still: Mad Men, AMC

Suits

Just like today, women wore suits in the office. They tended to be nipped in at the waist, with narrower skirts as opposed to the full skirts that were more common outside the office. Suits were often more feminine than what we think of as a business suit today. Vintage suits had more details, like trim and darts. Sleeves were often shorter for practical reasons, like keeping them from getting caught in, or soiled by, typewriters. A popular style was the box jacket, a boxy jacket that fell to just below the waist and just above the hip.

1950s black-and-white fashion photograph of two women in fitted tweed suits and small hats

Skirts and blouses

Whilst less formal than a suit, skirts and blouses were worn in the office too. Pencil skirts were popular, as were tie-front blouses.

Tips on how to wear vintage at the office

  • Don’t wear vintage head to toe. It really is too much for the office and gives the impression that you are in costume.
  • Be careful of wearing styles that are too body-conscious for the office.
  • Make sure your zips work too. They can be costly to change.
  • Some vintage styles might be too dressy for the office. Fashion, especially for the office, has become less formal over the years. So if a piece seems too dressy for work, accessorise it to make it more work-appropriate. Add a belt and a cardigan.
  • Leave the vintage make-up and hairstyles for after work. It is definitely too much for the office.
  • Don’t go crazy with prints and fabrics. It is easier to get away with vintage styles at the office if they are in one colour and aren’t made from 1970s polyester.
  • Don’t wear anything too dated. The goal is an updated, vintage-inspired look, not to look as if you are working in London circa 1957.
  • Vintage clothing is often easy to spot because it is a little saggy, missing a few beads and has some pilling. Don’t wear anything that isn’t in tip-top shape and condition.

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