What Do You Wear with a Maxi Dress in the Winter?

Layering up your maxi dress in winter
Learn how to stay chic yet toasty in a maxi dress this winter season by layering the right way. A great way to keep warm and look great in your maxi dress.

Like you, the picture that comes to mind when I think of a maxi dress is bright summer fabrics with sandals, sunglasses and a wicker bag. But these ankle-skimming dresses aren’t just reserved for warm weather.

Style stars like Nicole Richie have proved that a maxi dress can be an even more eye-catching option in winter. It’s long enough to cover your legs, versatile and allows you to still look and feel feminine in an otherwise gloomy climate.

But knowing what to wear with a maxi dress in winter can also be challenging. It’s not as easy as throwing on some sandals and sunglasses; you have to be creative, warm, and stylish at the same time.

Luckily, we have some fun ideas for you, and they are things you already have in your closet.


You don’t really wear pockets with a dress, but you get my point. There is nothing better on a cold day than keeping your hands warm. Gloves do solve that problem, but pockets give you an extra layer of fabric and allow you to keep your hands close to your warm body.

A Fluffy Coat

Having mentioned the obvious, I’ll start with the upper part. Dressing up a maxi dress in winter calls for some layering. The easiest way to stay warm and cozy when wearing a maxi is to throw on a wool or puffy coat over it.

There are two ways to do this; wear a medium-length wool coat or a long ankle-length coat. Long coats paired with a maxi dress are straight out of the fashion book, and it’s a style that never fails. For best results, get a coat longer than the dress to structure the whole look.

Sometimes though, a coat is not enough layering, especially if your dress is lighter. I find that wearing a long sleeve turtleneck underneath the dress brings in a cool layered factor and more warmth.

A Chunky Sweater

Fluffy coats can be heavy and unstylish most of the time, so I avoid them when I can. The best alternative when it’s chilly but not freezing cold is a chunky sweater over the maxi. Wearing a contrasting color of sweater turns your maxi into a stylish skirt.

This is a really great casual look, and you can throw on a warm t-shirt underneath the dress for layering purposes.

Fitted Jacket and Blazer

Many of us have done the maxi dress/leather jacket look during spring and sometimes the fall season. It’s a great way to style and layer a maxi when it’s a little breezy. In the winter, however, you can throw on a turtleneck underneath to add some warmth.

Switch the leather jacket with a structured blazer when going to work or a meeting, and no one will question that look. Maxi dresses have a summery and free-spirited reputation (just look at how many floral maxi dress options there are out there!) but a good blazer tones down that image for a more refined look.

Warm Vest

There’s something so stylish and regal about wearing a woolen vest over a flowery maxi dress and finishing it with high heel boots. The vest is heavy and warm, but you have to leave the chest area open and the arms, of course. This means you must add something underneath like a light sweater or long sleeve turtleneck to cover the arms and chest.

It’s a classy, sophisticated style that makes you look like a celebrity without trying so hard.

Tights and Leggings

Now that the top part is covered, let’s warm up the legs. As long as a maxi dress is, it’s not enough to keep your legs warm during winter. This is why you need to wear some leggings or warm tights underneath. The secret here is to ensure they are not visible, so the dress must be long enough or the shoes must cover them.

Leggings are not your only option, though. If you have a button-up maxi dress, wearing it with tight pants looks really good. Wear a pair of tight leather or jean pants underneath and keep the dress open from the waist down. You can also do a belt at the waist to add structure to this look.


Boots boots boots. This is all the shoes you need during winter. Knee-high boots, high heel boots, ankle booties- whatever you like will be very useful in these three cold months. Of course, the style of boots you choose has to go well with the outfit.

For example, the open maxi dress and pants look go great with high-heeled boots, while ankle booties complement a more relaxed casual look.

That said, you can also do sneakers or any other closed shoes if your area isn’t laden with snow. The chunky sweater and maxi style looks really good with sneakers, and it’s easy to pull off.


Maxi dress accessories in summer and spring mean jewelry, statement handbags and sunglasses. In winter, however, the job of accessories is to add warmth; hence you are looking at a bright scarf, gloves and a winter hat.

A belt also comes in handy to add structure to an otherwise boring look. That is really all you need because nobody will see the jewelry on your neck or hands anyway. If you must, a popping pair of earrings will bring the look together, so consider bright colors like gold loops or pearls.

As for handbags, try to keep it light and small because your clothing is too heavy already. A small sling bag or light tote is good enough as long as it brightens up your outfit.

What do you wear with a floral maxi dress in the winter?

When styling a floral maxi dress in winter, your purpose is to add warmth and tone down the summery vibes. You, therefore, need a darker coat, jacket or chunky sweater and high heel leather boots or sneakers. Keep accessories minimal with a winter fedora and small purse, and you are good to go.

How do you stay warm in a maxi dress?

Layering is the best way to make a maxi dress warm enough to pass for winter attire. You can wear a long sleeve turtleneck underneath the dress and then layer up with a coat, sweater or warm jacket. Keep your legs warm with some tights or leggings and closed shoes like boots or sneakers.

Lior Shapiro

I love clothes with pockets and dresses, and I think any woman can pull off a good maxi dress.
I believe women's clothes with pockets make the world a better place.