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How to wear 2 leather items without looking like a rocker

#fashionover40 woman in a fake suit in leather
#fashionover40 woman wearing leather on leather
Lookbook Store motorcycle style inspired leather jacket with Sienna Studio leather pencil skirt (similar here), Jeanne Pierre sweater, Pavalo Russian scarf, GNW tight and Harley Davidson booties (all own)

Leather fashion over 40 is tricky, especially when it comes to wearing two leather items at the same time. While younger women can get away with the biker chick style, at 40+, motorcycle leather pants with a motorcycle jacket may look past prime unless you are sitting on your Harley with your helmet on.

#fashionover40 woman in a fake leather skirt suit
Back view of outfit with leather motorcycle style inspired Lookbook Store jacket, Sienna Studio skirt, GNW tight and Harley Davidson booties (all own)

Unless you ride a bike, we 40+ are often told not to wear leather. Who hasn’t seen on pinterest the quote of Edith Head

Only Roy Rogers and Marlene Dietrich should be allowed to wear leather trousers.

Think about it! Both of them are known for their great style and taste. For my money, the quote means you really need to pay attention to get it right and to not look like Miss Whiplash’s auntie. Now when it comes to two leather items in an outfit, you will have to be even more alert on that you don’t look like trying to hard or not trying at all.

#fashionover50 How to wear leather on leather and look effortlessly chic @ High Latitude Style @ woman in pencil leather skit and leather motorcycle jacket
Side view of the above outfit. The outfit works as the skirt is a classic pencil cut (i.e. it would not work on a bike) and the jacket has a blazer cut with motorcycle inspired embellishments. It would not work on a bike either

Leather is part of my signature style. As I pointed out in last week’s post on looking posh in leather over 40, tailoring is key. The leather items should have a classic tailored cut, and it should not be the original motorcycle pants or jacket cut. The same applies to bomber jackets.

How to wear leather-on-leather


When wearing leather with leather combining suede with plain leather is the safest because of the different textures (see example below with suede skirt and leather top). Different colors of leather work well too. A fool-proof way is to wear a leather top or jacket underneath a leather coat. Unless you wear the coat open, the leather-on-leather is not visible. Even when the coat is open, it is more forgivable. Many people do not consider outerwear as an outfit that needs styling. However, I am a strong believer that one should style the outerwear and consider it as an outfit as well.

When styling a leather-on-leather outfit pick classic items in high quality leather. Go for neutral colors like black, blush, tan, gray, cream or white. Red and oxblood/marsala/burgundy and red are options for the more daring 40+ woman. However, only wear colors that flatter you. Make wearing leather-on-leather the statement of your outfit, i.e. let the accessories play a supporting role and the leather be the star.

Try out leather items you want to wear together and make a couple of photos with your cell phone. Best, have someone take them. Then have a look at the outfit photos and pick the leather-on-leather look that looks the most flattering, i.e. the one that looks the best “wrong” in the sense of the old fashion rule not to wear leather over 40. 😉

Examples of leather-on-leather looks

Here are additional examples of leather-on-leather outfits that I wore to work.

#styleover40 woman in leather skirt and jacketExample fake suit: Oliveo leather skirt with leather jacket, hat, scarf tied as a bow, and pumps (all own). This outfit has a slightly British eclectic vibe#fashionover40 woman in leather coat over suede jacket and leather pantsExample outerwear over pants and suede: Boxy leather coat with Orvis suede blazer, INC leather pants (similar here), Michael Kors leopard print satchel bag, Coach booties and silk printed scarf (all own)

#styleover50 woman in suede skirt and leather topExample top with skirt: Leather top with G-III suede skirt, leopard print scarf, Modalo Pippa bag, gray T-strap pumps (all own). The scarf ties the color of the pumps and top together

#maturefashion woman wearing a leather coat over a leather skirtExample coat with skirt: Leather coat (similar here), Oliveo leather skirt, GNW Luxe sweater, Christian Louboutin pumps, LV saddle bag, and sunglasses (all own)

#midlifefashion woman in leather pants and shearling jacketExample shearling jacket with leather pants: Andrew Marc shearling jacket with INC leather pants (similar here), 3.1 Philip Lim bag and Clarks booties (all own)

#maturestyle woman in leather pencil skirt and shearling coatExample shearling over skirt: Cole Haan shearling coat with Sienna Studio leather pencil skirt, GNW tights, Harley Davidson booties, 3.1 Philip Lim bag, gloves and fedora (all own)

When you liked this post why not sharing it by tweeting to your friends how to wear leather on leather and look effortlessly chic.

Do you wear leather? How do you wear your leather clothes? Have you ever tried to wear two leather items in one outfit? Tell me your styling problems by email so I can help you in the next Agless Style series post.

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Photos: G. Kramm (2015)

Copyright 2013-2017 Nicole Mölders | All rights reserved

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