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Orvis camouflage floral print utility jacket, Keep Calm Let the Meteorologist Handle It T-shirt, Oliveo leather skirt, Steve Madden fall sandals (all own), and green wood watch c/o Jord

Maxi skirts are a summer thing. Maybe because maxi skirts would just plow snow or get wet in winter. But maxi skirts in leather are a different beast and winter suitable. This style guide provides the tips to look stunning with provides tips and tricks how to style a maxi leather skirt in all seasons.


  1. What to wear with a maxi leather skirt
    • Try the maxi leather skirt with a cardigan
    • Long over long and over short
    • Pick two colors and work with their different saturation
  2. How to wear a long nappa skirt on dry, below freezing winter days
  3. What Outerwear Goes With a Maxi Skirt
  4. Which Jackets to Wear with a Maxi Skirt?
  5. Wrapping Up How to Wear a Long Leather Skirt


Disclosure: There are affiliate links in this post.


What to wear with a maxi leather skirt

When I saw the long hems on the runway at fashion week, they called my name. When you are a regular reader you know  I have loved leather since I was a child. Thus, I bought this tea-length beauty in cherry red. It’s perfect for windy, but dry weather when temperatures are in the 50 to 60F (10 to 15oC.) Of course, tights underneath permit wearing the skirt also at temperatures below the freezing point.



Try the Maxi Leather Skirt with a Cardigan

In this post, I show how to wear a leather skirt that is almost floor length. This outfit example shows this cherry red A-line leather skirt with fall snake skin open-toe booties, a short-sleeve cashmere black knit sweater, and a gray cashmere cardigan.

Knot the tails!

Like with fabric maxi skirts, you have to balance the skin/fabric to not look old-fashioned. Thus, when it is already too cold to go bare legs, fake the look with pantyhose like in the inspiration photos below. Also you have to create a balance between the long skirt and whatever you wear on top. Knotting the tails of the cardigan “shortens” it visually, and adds some shape. The bold necklace that I made in a recreational class when I was in college, adds further interest. The bright cherry red added a pop of color to improve the mood on this rainy day in fall. Its leather is a great wind protection.



influencer showing How to Wear a Long Leather Skirt
Outfit details: Oliveo long leather skirt (similar here), Moda International cashmere cardigan, Moda International sweater, structured bag, Hermes collier de chien bangle, Bulova watch, unbranded pantyhose, open-toe snake print sandals, and DIY necklace



Long Over Long and Over Short

In the above look, the knotted tails of the cardigan create a long-under-short look. The look below shows a long jacket over the top, and hence a long-over-long look. Again the right balance for the horizontal lines is important for the look to work. Pulling the drawstrings a bit gives the illusion of a peplum. It creates some curves and highlights the waistline of the skirt. All these efforts serve to balance the look.


style blogger in casual look with leather skirt
Outfit details: Orvis camouflage floral print utility jacket, Keep Calm Let the Meteorologist Handle It T-shirt, Oliveo maxi leather skirt, Steve Madden fall sandals, unbranded pantyhose, studs, headband, Hermes collier de chien cuff (all own), and green sandalwood watch c/o Jord



Try a 3/4 Sleeve Tee

Another way to create a skin-leather balance is to go for a short-sleeve or 3/4 sleeve top. The outfit idea below features a 3/4 sleeve striped T-shirt with the nappa bottom. The plateau sandals add height which helps to not overwhelm the frame. A high heel is a Must for all petites when wearing anything “maxi.”

Create a tall illusion when you are petite.


fashion blogger in maxi leather skirt with striped T-shirt
Side view of maxi leather skirt outfit


midlife woman in maxi leather skirt
Outfit details: Oliveo long leather skirt with Dr. Scholl wedge sandals, DIY long pendant necklace, Festina watch, pearl studs, and striped T-shirt c/o Marine Layer



Pick Two Colors and Work with their Different Saturation

The following example shows this long cherry red leather skirt with a menswear cable-knit sweater and a big statement necklace in beige and rose. The necklace beads are a darker and lighter version of the sweater and skirt colors, respectively. The Hunter boots pick up the color of the beige strands in the necklace. The wide sweater offsets the slim cut of the skirt (or vice versa). This means the looks is an example of bulky  with slim.


fashion blogger over 50 in cable knit sweater with long leather skirt
Example long maxi skirt styled with oversize cable knit sweater, beret and cape


stylist in maxi-skirt in winter
Similar maxi leather skirt, unbranded oversize cable-knit sweater, Hunter rubber boots with wool socks cuffed over the boots, statement necklace and LeatherCoatsEtc winter white beret and tan gloves, Louis Vuitton bucket bag



Can You Wear Long Skirts in Winter?

Long skirts are a summer thing? No way! They are great on a dry winter day ! See the photo inspiration above. The temperatures just have to be low enough that even around the warmest time of the day there is no risk of snow melt. Under these conditions, long skirts are great. One can wear warm leggings underneath for nobody to see. Even long johns would work. Everything is covered up and the full length provides some protection too.

On windy days, leather is a great idea to keep the wind out. The piece gets a casual vibe with my Irish cable-knit sweater. To not make the long skirt and heavy sweater overwhelm a petite frame, wedge sneakers are a great option. They give some height, are comfy, and insulate the feet from the ground. A layering top underneath the cable-knit sweater provides for some extra insulation. When it is windy the wind chill gives the feeling of an even lower temperature than it actually is.


maxi nappa skirt with black cable knit sweater and wedge sneakers
Outfit details: Black Orvis Irish cable-knit sweater, Oliveo A-line maxi leather skirt, long necklace and Michael Kors camouflage wedge sneakers (all own)


When styling/picking your top, recall the golden cut, your were taught in arts class. The ratio of 2:3.

Do a half tuck with long sweaters to create an outfit in the rule of the golden cut.



What Outerwear Goes with a Maxi Skirt?

Long skirts are a summer thing? No way! They are great on dry winter days as well. Especially, when the material is leather. The temperatures just have to be low enough that there is no risk of snowmelt during the day. You can wear warm leggings underneath for nobody to see. Even long johns would work. Everything is covered up and the full length provides some protection from the wind too. However, you have to pair the maxi with a short jacket or cape to create a balanced outerwear outfit.

Keep the look balanced!



Casual winter look in maxi length
Front view of leather maxi skirt with short jacket.


mature woman in maxi A-line skirt standing in the snow
Oliveo maxi A-line skirt, Michael Kors wedge booties, Orvis Irish cable-knit sweater, LeatherCoatsEtc gloves and jacket


In the look shown in the photo below, I wear a long sleeve layering top under the sweater to provide some extra insulation. Note that coarse knits like this sweater are “cold bridges” (Read more on cold bridges in the post at the link). The air can easily enter or leave through the loops of the knit. Thus, a fisherman cable-knit sweater like this one is not a good protection from the cold in windy climates. Even in cold climates with calm or no winds like in Interior Alaska, wearing it needs some extra thoughts. My solution was to wear the cape shown below that does not easily let air in or out. Paired with the beret the outfit gets a French style twist.


fashion over 50 Winter look with cape and long leather skirt
Vintage cape worn over long leather skirt with oversize cable-knit sweater outfit accessorized with LV bucket bag, gloves, statement necklace, LeatherCoatsEtc beret and gloves, Hunter boots


When wearing rubber boots in snow, you need to wear wool socks in the boots. Rubber conducts the cold very well.  You would get quickly cold feet outside in rubber boots or Wellies without thick socks in winter. Actually, here I am wearing a pair of wool socks over the tights. Read more on avoiding cold feet in frigid temperatures.


Which Jackets to Wear with a Maxi Skirt?

style book author wearing a maxi skirt with a jeans jacket and plateau sandals in early fall
Outfit details: Hermes collier de chien leather band, Dr. Scholl plateau sandals, Great Northwest medium wash jeans jacket, Kate Moss for Longchamp satchel, Festina watch, DIY agate pendant  necklace (all own) and striped 3/4 sleeve T-shirt c/o Marine Layer


A waist or upper hip long jeans or (colored) denim jacket is a great cover-up to stay warm in the already cool morning and evening hours in fall.


Wrapping Up How to Wear a Long Leather Skirt

A floor- or tea-length hide is a style statement. It can be worn year round, but needs tights, leggings or long johns underneath in winter. Showing some skin is great in the warm season to balance the length. In the cold season, add height with plateau soles, heels or wedges to not overwhelm your frame. Outerwear should be cropped or nipped in at the waits and non longer than hip length to keep the look balanced.


Photos of me: G. Kramm

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