How to Wear Ankle Boots with Jeans...

The Dos & Don’t

Note: I love this look and ankle boots are my first choice.  A great fall/winter look.   Plus a feminine differential that always works.  Some great suggestions, especially the "Do Nothing" one.

Straight-A-Style by Amy Ann Arnold

Cropped Denim

This is perhaps the easiest way because your jeans do all the work for you. If you are wearing a cropped pair of jeans, they are already not going to conflict with your booties.

• Do let your denim hit above your booties
• Don’t let there be too much skin between the bottom of your jeans and the top of your booties. This may mean (depending on how cropped your jeans are) that you need a taller ankle bootie (one that hits above your ankle bone) as opposed to a shorter pair. In both pictures below, I am wearing one of my taller booties.

                   

Tuck Your Jeans In Your Boots

This one is the trickiest of all in my opinion.

• Do tuck your denim when it is very skinny at the ankle and will not bunch. It also has to be long enough to tuck.
• Do tuck your denim when your boots have a wider opening at the top.
• Don’t try to tuck your denim when your boots are very short (i.e. hit at your ankle), only when they are a bit taller.

Cuff Your Denim

• Jeans that are 1.) too long to naturally hit above your booties 2.) not super skinny at the ankle and/or 3.) may be paired with taller booties are great candidates to be cuffed. My jeans below are a great example because they are a thick denim that is pretty long and not super skinny at the bottom. Any bootie I pair them with really means they need to be cuffed because it causes them to bunch.
• Do cuff your jeans when they would otherwise bunch over your booties.
  

Do Nothing

• Sometimes your jeans are just regular length skinny jeans and your boots are ankle length, and there is no need to cuff or tuck. Win!
• Do nothing when your jeans are skinny/narrow at the bottom and hit just above your ankle.
• Do nothing when your booties hit at your ankle.