• emsteinbrink

Layer Your Dresses for Fall & Winter



There's no need to pack away your dresses just because the weather is getting cooler! Keeping your dresses in your fall and winter wardrobe is a great way to mix up your outfit rotation from the normal sweater and jeans combo. Plus, it works just as well for working from home as it does for a cozy outdoor dinner with friends or your partner.


Keep reading for some outfit inspiration to get you started! And you'll note that I've got some layering tricks to help you stay extra warm on those cold Fall and Winter days. (a must where I live in the Midwest!)


Outfit 1

Dress + Sweater + Boots

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I love this cozy way to style your dresses for fall. The pieces to pull this together are really simple:


1) Dress. I love the midi or maxi length best, although a shorter option can work as long as it's flowy.

2) Cropped sweater. A cropped sweater or one that hits your waist sweater makes it easier to get your proportions right with this outfit. Another trick is to wear a belt and partially tuck the sweater into the belt to get the right proportions.

3) Boots. Ankle, mid-calf or tall boots all work! I love this western style bootie in the outfit above for a cool, on-trend look for this fall.


Extra warmth trick:

Add a turtleneck underneath the dress for extra warmth. Also add a pair of warm tights to keep you toasty outdoors! If you opt to wear tights with shorter boots, make sure that they match for a more cohesive look. (i.e. black boots with black tights)


Shop my favorite warm layering tights here!


Outfit 2

Dress + Moto Jacket + Turtleneck + Tall Boots

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How classy and cool is this look?! I'm already thinking this would be an amazing outfit for Thanksgiving gatherings coming up. Here are the key pieces to make this look just right:


1) Dress (again, go with a longer length here - either midi or maxi). A patterned dress looks amazing, but a simple solid color works, too!

2) Turtleneck. This is a great way to stay warm, but also makes this style look cozy and perfect for fall or winter.

3) Moto jacket. You may already know I love a "soft and hard" mix up in any outfit, and the addition of a Moto jacket to this look really gives it the cool factor! Find a roundup of my favorite Moto jackets here. (Hint hint... BlankNYC is a favorite brand of mine!)

4) Boots. Personally, I think the tall boots make this outfit, but ankle length boots can work, as well.


Extra warmth trick:

Again here, add a turtleneck underneath the dress for extra warmth and a warm layering tight. Shop my favorite warm layering tights here!


Outfit 3

Dress + Blazer + Belt + Sneakers

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Finally, here's a third idea for styling a dress this fall and winter. I love how fun this look is with the mix of casual sneakers and the polished blazer on top. Here's how to pull it off:


1) Dress. Pick a dress of your choice. By now you can guess I'm going to recommend a longer length especially since this one isn't paired with boots. I also love the flowy, oversized look of this dress above, making it feel even more casual.

2) Blazer. Add a blazer of your choice! I love tweed, houndstooth, and plaid for fall, but go with what you have! If you have a solid dress, consider adding a patterned blazer - and vice versa. It's all about balance people! Want to do some pattern mixing? Learn how to mix plaids with patterns right here.

3) Belt. Personally, I'm a big fan of belts, and it does two jobs in this case: One, it gives you some shape. It is really easy to lose your shape or add unnecessary volume in a billowy dress like this so adding a belt can help define your waist. And two, it adds an interest element and detail to this outfit.

4) Sneakers. The casual look of the sneaker really pulls this whole look together and balances out the serious-ness of the blazer. If you're into combat boots, that would also be an acceptable swap for the sneakers in this look!


Extra warmth trick:

Again you can add a turtleneck underneath the dress for extra warmth. If you opt for combat boots in your look, you can wear tights in a matching color to keep you warm. Shop my favorite warm layering tights here!


Here's two ways I styled a floral midi dress this week. You can see my belt trick for getting your sweater length just right in the left picture.



For more outfit ideas and my curated wardrobe picks for Fall, including top affordable denim picks for Fall, favorite suede Moto Jackets, and my favorite wool coats for fall, you can shop it all on my site here.

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