How to Wear Maxi Dresses in the Fall: 5 Style Options
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  • Writer's pictureBrenda

How to Wear Maxi Dresses in the Fall: 5 Style Options

Updated: Sep 28, 2023

Maxi dresses are a girly girl's favorite item during the Spring and Summer but who says they can't also be worn as a transitional Fall piece?

This wardrobe staple comes in so many styles, different colors and patterns that it only makes sense to want to be able to wear them across seasons.

If there's any season to carry a maxi dress apart from Summer, it would be Fall. Why? Well it's thanks to the layering technique most commonly used in the Fall.

I would have said Winter but living in Canada means there's typically inches of snow on the ground and that's not the type of weather you want to be caught up in wearing a maxi dress.


We tend to think of a maxi dress as just a Summer staple. We pair it with sandals, flip flops or sneakers and enjoy time spent in the warm weather, comfortable in our long flowy dress. Maxi dresses have always been a great way to look a little more dressed up when it's hot outside while staying cool and comfortable.

However, in this post I shall be showing you how to take your summer maxi dress worn during the warmer months, into the Fall season. Different looks appropriate for the chillier season would be achieved through the use of cozy sweaters, jackets, blazers, boots and longline coats. You would be able to rock these looks as not only casual wear but even for formal events.

*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

1) Add a sweater on top

Probably one of my favorite ways of turning my Summer maxi dresses into Fall maxi dresses is by adding one of my oversized sweaters on top of it. Mind you, the sweater does not have to be oversized but a looser sweater does work best for this style.

Your maxi gown now looks more like a long skirt since the top part is covered and I have already talked about choosing your footwear to avoid looking frumpy. This look is a great option to go with if you're out of ideas on what to wear to the office or if you're just looking to try something different with your wardrobe.

Image source HERE

I've said it several times on the blog: clothing is meant to be used and re-used. The more versatile it can be, the better, especially in this economy. Adding a cozy cardigan on top of your maxi dress gives you a more casual look and so you could definitely wear this out for a casual date night, to meet up with the girls or for a nice Fall walk.

Get a similar look HERE

2) Wear a sweater underneath

During the cooler months, a perfect way to look chic but stay warm is by adding a sweater underneath your maxi dress this time. A thinner, lighter sweater should be used here instead of a chunky one made from heavier fabrics to avoid looking bulky up top.

The best maxi dresses to try this look with are ones with thin straps, that way your shoulders can be seen and this would make you appear slimmer, even with the extra layer underneath. I personally prefer to go with a thin black turtleneck, or one in a neutral color, especially if my maxi dress has some bold colors on it already.

Image source: HERE

You can choose to add either a leather jacket, denim jacket or longline coat to complete this look along with an ankle bootie. Remember that ankle booties work better with long dresses and skirts because no one is seeing the rest of your foot under your floor-length dresses.

During the winter seasons, you could wear a pair of leggings as well underneath your maxi skirt for some extra warmth and no one would even know.

Similar sweater HERE

3) Add a shirt underneath and throw on a denim jacket

If it's not yet too cold outside, a white shirt could be the perfect piece to add to your casual maxi dress and take it up a notch. I would recommend going with a white button up dress shirt - as I have talked about in this post and if necessary, adding a light jacket on top. If some form of outerwear is needed, a jean jacket is a great option to go with if you're going for a more casual look.

Image source: HERE

For a more sleek look, grab your moto jacket and a pair of boots to really rock this Fall outfit. Maxi dresses that would work great for this look would be a floral maxi dress or any maxi dresses in solid colors.

The white shirt would provide neutrality and the solid color of your outer layer would also ensure there's minimal color clashing. As most of your body is covered with this look, it's one maxi dress outfit that works for any body shape.

4) Add a leather jacket

Adding this wardrobe staple to your look instantly adds some spunk to an otherwise basic attire. A black leather jacket is the best way to turn you breezy maxi dress into a Fall show stopper.

The rest is simple - you can throw on a pair of boots (even combat boots if you're feeling really spunky) and some gold jewelry to soften things up a little. A brown biker jacket could also work nicely with your knit maxi dress and I even talked more about styling one HERE.

Image source: Here

Get the look HERE

What I love about wearing a short jacket with a long dress is how it ends up elongating you, especially if your boots are heeled. If your maxi dress has floral prints, then a brown jacket may actually work better for you as black may be a little too harsh. A cute tote bag could also make this look more feminine.

Image source: Here

5) Add a belted blazer

A well-structured blazer can hold you in the right place and is one of the most versatile pieces. It's only normal that it would be added to this list. If you wish to look a little more formal in your maxi dress, try adding a blazer on top of it.

A wrap maxi dress or a strapless maxi dress would work amazing with this look because they're already dressier. All you would need is a statement necklace to top it all off. This is such a great look to go with for a Fall wedding or any wedding held in cooler weather.

Image source: Here

A style tip for you: for some extra formality, add a slim belt on top of your blazer to really accentuate your waist if you worry it's getting lost in your outfit. A blazer with puff sleeves is also a great idea if you have narrow shoulders and are bottom heavy. It would draw attention to your upper body, thus balancing things out overall.

Get the look HERE

These 5 different ways to style your maxi dresses show just how easy it can be to create simple Fall outfits using key pieces from your Summer wardrobe. I hope you won't be too quick to stow away your summer maxis after reading this post and realizing that they could be that transitional piece you're looking for before you're forced to throw on a full-blown winter jacket.

Regardless of your body type, or the type of maxi dresses you own, you can definitely pull off all of these looks. It's just a matter of coordinating the colors and prints.

Until the next post,



For more inspiration, check out my post on how to wear white booties in the Fall.

I also have a post on how to wear a pencil skirt in the winter, which could serve as a great guide.

Headed to a pumpkin farm? Check out my post: 11 Outfit Ideas to Wear to a Pumpkin Patch in the Fall for some great outfit options.

Check out my post on 8 ways to wear a denim shirt for some more style inspiration.

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