Dressing Tips · Fashion · Seasonal Guide · Style

How to Embrace the Bootie Trend This Fall

This is a little Fall Guide Preview… Our Fall Guide will launch next Monday, September 16th!

I did a poll on Instagram last week about what people wanted to see for fall. One of the questions I got was how to know which type of booties to wear with what length of pants.

Booties are definitely a little harder to style depending on their height. It also feels like you need a million different ones to go with pants or skirts or dresses. I am breaking it down to the 5 styles that are most important and what they will go with in your closet.

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Dress // Shoes (similar) // Necklace

Low Profile.

This style will basically go with everything. Generally these booties can be confused with a shoe which gave us the term, shooties. Depending on the style this type of bootie will take you from the office to dinner and anything in between. My dressier booties are always low profile because I can wear them with any of my pants or dresses.

Cheat Sheet…. Mini, Midi and Maxi length skirts and dresses. Skinny jeans. Boyfriend jeans. Flares. Cropped length pants.


Flat boots are usually your most casual boots. They are going to be more functional for walking and standing but if you are looking for something dressy with a flat heel I would opt for a ballet flat.

Cheat Sheet… Cropped length pants. Midi Skirts. Mini Skirts. Dresses. Skinny jeans. Full Length pants. Boyfriend Jeans.


Ankle boots are going to hit you slightly above your ankle bone. These booties are going to start looking less like a shoe and more like a boot for sure. Once you start getting to boots that come up to the ankle you want to make sure they have a zipper or snaps to get them on and off.

Cheat Sheet… Cropped pants. Skinny jeans with a cuff. Midi skirts. Mini skirts. Some Maxi length skirts.

Above Ankle.

These are going to be your booties that are at least 3″ or more above your ankle bone. These are your more substantial booties and depending on the heel can look casual or dressy.

Cheat Sheet… Cropped pants. Midi, mini and maxi skirts. Full Length Pants.


This is really getting out of the bootie territory and more toward the boot range but I wanted to include them. Mid Calf boots are going to be really popular this fall and that is why I wanted to talk about them. These types of boots are really important to try on so try to find them in your store or make sure you get free shipping and returns. Check the shaft size when you are ordering to know what part of your calf these boots are going to come to.

Cheat Sheet… Skinny Jeans. Midi and Mini skirts.

I always like to give this reminder too. With shoes it’s important to make sure that you get the right fit but it is especially important with boots. It’s incredibly uncomfortable to have boots that are too tight or are a struggle to get on each time you want to wear them. Always make sure your boots are right!

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