How to Wear Maxi Skirt in Winter

My daughter says that winter is where fashion goes to die. This is true for most people unless you love maxi skirts and dresses. As others move their beautiful summer outfits to the back of the closet in readiness for winter, we are doing none of that.

After all, nobody around here was wearing booty shorts and miniskirts in hot weather. We are a maxi tribe year-round, with occasional visits to the jean and midi skirt closet.

I recently did a how-to-wear a maxi dress in winter as well so you can check that out, even as we explore the skirt option.

Granted, you can’t wear a maxi skirt in winter like we do every other day. Those crop tops, sandals and stilettos have no place in this weather. But instead of showcasing specific maxi skirt outfits for winter, I’ll start by giving you actionable tips for pulling off maxi skirts in cold weather in style.

Tips for Staying Warm in a Maxi Skirt

1. Layer Up.

There is no way around this if you want to stay warm in winter. But unlike most people who layer up with winter jackets and ugly sweaters, I recommend doing the layers underneath.

I usually start my winter outfits with a base layer of a warm turtleneck and leggings. Sometimes I also do a t-shirt or a long sleeve bodysuit under the turtle neck for good measure. Make sure you also wear socks because feet can allow a lot of cold into your body.

With this base layer, you can wear any outfit without all those ugly heavy coats. Sometimes it will be necessary, especially if you are going outside but you don’t have to.

2. Don’t Be Afraid of Color

I understand why people say to stick to a winter color palette. Black, emerald green, brown, muted grays and purples are all very thematic and still beautiful. But it is all these dark colors that make you look and feel like you are in mourning.

(Wondering what to wear with a black maxi skirt? Here’s a guide for you)

Injecting a bit of color into your winter outfit will brighten things up and help you stand out. Sometimes I wear neutral-colored maxi skirts, except white, and also wear bright-colored coats and boots. But if you want something a bit safe, try wearing a bright-colored top such as white, pink, red and green.

3. Define Your Waist

Another reason winter fashion looks so bad is the fabric overwhelm with no shape. You can quickly solve this by defining your waist with a belt or tucking in your tops.

Even when I’m wearing a thick oversized cardigan or sweater, a statement belt helps to cinch in the waist and create some shape. You can also achieve this by tucking the front of the sweater into your skirt and then leaving the coats open.

4. Wear Warm Shoes

This should go without saying, but sandals, stilettos and all open shoes are out in winter. You can try wearing them with socks, but the look doesn’t always work.

Instead, opt for closed warm shoes such as boots and sneakers. I recommend going for knee or thigh-high boots because they keep your entire legs warm, unlike ankle boots. They are also the perfect way to hide socks and leggings. That said, ankle booties do work better with straight skirts.

For a more casual look, I like wearing trainers and sneakers. They may not be the warmest option, but they do the trick if you have leggings on.

5. Consider a Casual Look

The coats, scarf, and boots make many winter outfits look heavy and serious. I have figured out how to wear a maxi skirt casually in winter without all the heaviness. You will still need the base layer for warmth and probably a sweater over the turtleneck.

But instead of a coat, you will rock your favorite leather biker jacket or denim jacket.

And instead of boots, you will do trainers. This look with a pleated or tiered maxi skirt is extremely casual but oh-so stylish; you won’t feel like it’s winter.

I rocked the same look with a cropped hoodie and a leather jacket over it.

6. Embrace Seasonal Accessories

The perfect winter ensemble must include seasonal accessories for style and warmth. Shawls and scarfs add some much-needed coziness, and they are still very much in fashion.

And while I hate to admit it, you will also need felt hats for your head and ears. Note that I said felt hats and not beanies because we are way past that and trying to look fashionable. A nice felt hat, paired with jewelry and the right outfit, makes you feel like a London princess every damn time.

Wearing winter gloves goes without saying, especially if you are headed outside. The last thing anybody wants is frosty fingers.

But the one accessory rarely discussed is the bag. Besides being dark and leather, your winter bag should also be big enough to hold some of your winter essentials. You will be throwing the gloves, the felt hat and a lot of other stuff in there.

How to Wear Maxi Skirts in Winter to the Office

There are plenty of stylish ways to wear a maxi skirt for work in winter. They all involve a structured blazer or long coat, and you need the base layer we discussed earlier.

One of my best ways to style a maxi skirt for work is to wear a stylish blouse over the turtleneck and tuck it in. Sometimes, I wear a warm long sleeve t-shirt underneath the turtleneck for extra warmth. I then throw on a blazer and pick the proper boots for the day.

But as you can see from this photo, you don’t need the blouse. You can just wear the blazer and accessorize with jewelry or a belt and a nice handbag. Keep the colors light or neutral to avoid feeling gloomy all day.