top of page

To Cuff or Not to Cuff...

… jeans with booties.

Booties are so fun and a fantastic way to keep your fall looks stylish. I’ve had a few people ask me lately about how and when to cuff jeans with booties and reckon there may be others with this question.

Here are three different booties I own and how I cuff them to make them work for me!

Flat boots with a loose top:

You don’t always need to roll your jean cuffs when wearing booties.These booties have a special place in my heart as I bought them in Italy! I love the edgy feel of them. My preferred way to wear them is with no cuff (third photo), however with the right outfit I would wear a small messy cuff (middle). The large cuff makes my legs look shorter than I’d prefer.

Mid height booties:

I spent many years looking for a mid healed bootie that I love, and these black suede Cole Haan’s stole my attention. They hit right around my ankle and the no cuff look make my legs look too lanky while high cuffs make them look too short. The small double roll is just right!

High Booties:

These are my Frye boots…I love love love them. They land just above my ankle and have a higher heel. For both those reasons it’s best to do one larger cuff. Straight legs (picture 1) make my legs look lankier than the previous booties. (If you don’t want to cuff your jeans - wear a longer top to provide balance). The middle style is a little off balance, so the third is the clear winner.


First and foremost, before you step out with any style or trend like a jean cuff ask yourself: ‘do I like the way this looks on me?’ Don’t feel you need to wear it just because it looks great on someone else. I am a believer that you can pick and choose looks and trends based on your style personality.

When you are wearing your booties with jeans pay attention to proportions of the entire look as well as how high it lands in relation to your ankle. You can cuff your jeans to create the illusion that your legs are either shorter or longer than they really are! If you want to know more about proportions, consider hiring me for a private session.

Additional tips:

  • You can wear a cropped style jean if you’d prefer not to cuff them, they should just skim the top of the boot.

  • Make sure the jeans look good cuffed…there are some jeans where the inside just won’t work, so think about rolling them under instead.

  • Match the height of the cuff with the height of the bootie – In most cases: the higher the bootie the higher the cuff.

Always remember to #dresstoconqueryourworld.




bottom of page