Leather jacket outfits for women: wear it over a long skirt

My stance: retire the skinny jeans. A short leather jacket over tight denim was the 2010s uniform, and it now reads as a date stamp. Over a long skirt, the same jacket looks deliberate, because the hard leather meets something soft.

The jacket itself is older than any of us. Irving Schott made the first Perfecto in 1928 and named it after his favourite cigar, and Marlon Brando wore one in The Wild One in 1953.

Quick facts

• Jackets: CAD 700 to CAD 845, read 5 November 2026 on within.
• Long skirts: CAD 399 to CAD 1,170.
• Leather dress: CAD 899, 100% lamb leather.
• Boots: CAD 2,050 for a back zip boot in full grain leather.
• Shipping: all 3 shops below ship to the US, the UK and Australia.
• First Perfecto: 1928, by Irving Schott in New York.

The jacket

Soia & Kyo, founded in Montreal in 2004, makes the Miu leather jacket in black lamb leather, CAD 845 at Due West. Lamb is softer and lighter than cowhide, so it moves when you walk instead of standing up at the shoulders.

For a jacket with a story, a pre owned Supreme Smurfs leather varsity jacket in size S is CAD 700 at Utopia, a resale shop. It is a men's small, so it sits roomy, like a bomber.

If you have no jacket yet and want the shape without the leather, Patou's oversized denim shearling jacket in grey is CAD 799. Check any used jacket with our leather jacket checklist before you pay.

Under it: the long skirt

Patou's Wave Milano long skirt is black viscose knit, CAD 399, the cheapest way into this outfit. Jean Patou opened the house in Paris in 1914.

Litkovska's ruffled midi skirt in black is CAD 1,170. The ruffle swings under a cropped jacket, and the contrast is the whole idea.

Patou's long volume skirt in white, CAD 499, does the opposite: black leather over a white skirt, which reads summer even in October.

Hard leather on top, something soft below it.

Or a dress, also in leather

Helmut Lang's Nappa bubble dress is 100% lamb leather, CAD 899. Under a leather jacket it is a lot of leather, which is exactly why it works on a night out.

For a quieter top half, Pleats Please Issey Miyake's basic pleated pullover in black is CAD 425. The pleats show at the cuffs under the leather sleeves.

The boot and one bracelet

Guidi, a tannery in Pescia since 1896, makes the R22V back zip boot in full grain black leather, CAD 2,050. A midi skirt should stop above the boot shaft, never at it.

Tom Wood's Robin duo bracelet is CAD 349. Silver on the wrist, by the leather cuff, is all the jewellery the outfit needs.

You will find the skirts, the dress and the boot at WDLT117, a designer shop. All three shops ship to the US, the UK and Australia, per each product page on 5 November 2026.

More combinations are in the leather jacket outfits edit and on our leather jacket outfits board on Pinterest. Schott cut the Perfecto for riding a motorcycle, and it has outlived the reason by a century.

Common questions

What to wear with a leather jacket for women?

A midi or long skirt, a slip dress, or a fine knit with wide trousers, and a flat boot. Patou's long black knit skirt is CAD 399, read 5 November 2026.

Can you wear a leather jacket with a dress?

Yes, and it is the best way to wear one. Pick a dress that falls below the knee so the short jacket and the long hem balance.

What shoes go with a leather jacket?

Leather boots with a low heel, loafers, or plain sneakers. A back zip boot under a midi skirt keeps the line clean.

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