Five Ways to Style a Dress for Fall

Transitional seasons are a tricky time to dress appropriately for both the weather and the season so today I am showing five ways to style a simple dress for times like this. I am using this Target dress I picked up last year, but many types of dresses will work, especially the “fit and flare” type that hit at the waist.


Let’s start with the basics. You can wear the dress on its own, especially if warmer temperatures allow, and use simple accessories to complete the outfit. I don’t like too many accessories, so I opted for a navy belt and gold necklace here. Other suggestions would be a silk scarf around the neck, or a classy, vintage brooch on the collar.



An easy & practical way to change the look of this dress is to simply add a sweater/cardigan. This would be a great look for mornings where it’s cooler outside because you can always remove this layer later on as the day warms up. The key to picking the right cardigan is all about the length. You either want it to hit significantly below the waist of this skirt (as shown), or right at the waist. The in between areas may throw off proportion, so use your best judgement. I also believe 3/4 length sleeves are the most flattering when layering over a dress (as shown), however you can also cuff the sleeves on a cardigan that’s too long.


Button Down Shirt Layered Under

Wearing a button down collared shirt underneath the dress is one of my favorite ways to style a dress like this when I’m looking to do something unexpected. It still looks polished and helps bridge the sleeveless dress into fall. When trying this look, be mindful of the neckline of the dress. The neckline shown below is high which makes this look easy to pull off, but a v-neck dress may be a little harder to make this look work. Regardless, it’s a fun way to experiment with your wardrobe and try an outfit that’s cute and functional.


Blazer Over Dress

Blazers are a great investment as they keep you warm like a jacket while giving your look a prep school vibe. Blazers and dresses balance the tomboy and girly style with perfection, which is why I’m drawn to this type of look. Again, be mindful of proportions as a blazer may not look so great with a long, maxi dress. A dress that tapers in at the waistline and flares out is your best bet for this blazer/dress combination.


Button Down Shirt Over Dress

Lastly, one of my new favorite ways to wear a fall dress is to make it look like a skirt. I don’t own any high-waist skirts, so this is a way of achieving this look. Just layer the button down shirt over the dress, button the top few buttons down to the waistline of the dress, and tuck the rest of the shirt underneath itself and tie it off. This look works best with a lightweight button down. I tried it first with the oxford cloth button down that I wore in the look above where I layered it under, but it was too heavy of a fabric to work right. This chambray shirt worked perfect because it’s lightweight and also gave it more of a casual style especially when paired with the booties.



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