• Amazing Gray

How to: Wear Booties with Jeans

For those who have been stressing over the length of jeans to height of ankle boot ratio for months now...my apologies. This post should have been done months ago.

Small disclaimer: The jean/ankle bootie situation is really not a black-and-white issue. There are many correct ways to wear your jeans with ankle boots and few ways not to wear them. A lot of this is based on your preference. For those Type A personalities out there, I know that is not what you want to hear. You would probably prefer someone to just tell you, in a cut and dry way, how to wear them. So, it if helps you can just take my opinions here as gospel truth and run with it. If options are overwhelming for you, then you can also take my suggestions and stick to them. I tend to see fashion in more grays than black and white (shocking, I know), so I rarely draw hard lines on such topics. It's all about preferences. Unless we start talking about Uggs, bedazzled denim or leggings as pants. I have very strong feelings on those topics. That's for another day...

To simplify everything, here are the two ways you should not wear your jeans with booties:

Tucked inside


Pulled outside

A cryin' shame.

These just look ridiculous. There is no other needed explanation than that. The key to wearing these two pieces in unison is to have just a bit of your ankle peeking out. This is usually done by rolling your jeans. "But how and how much and why types of jeans roll?!" you may ask. Let's not freak out. It is only pants and shoes so don't overthink it.

I have chosen all of these looks with skinny jeans. That is the most common cut of jean you have probably seen styled with booties. It is generally the look most people are going for. However rolling boyfriend jeans, straight leg or not-so-skinny skinny jeans with booties will still look great. It is a more casual, loose look but totally acceptable. Don't believe me? Would you believe Jessica Alba?

I would like to take a second to note that all of these looks are age appropriate for all ladies! So before you start thinking, "I wonder if I am too old..." stop. No, you are not too old. Ok. So you have your basic pair of skinny jeans and your basic ankle height booties (as in, hits around the ankle bone or a bit above. I don't think this is a fine science.). You have two solid options -- roll them twice or use one larger cuff.

Again, just a little bit of your ankle peeking out. Roll the jeans twice (maybe get about an inch-ish of denim in each roll...for those that need specs) and don't make it look perfect. Messy it up a bit! Or you can do a neat, 2 inch-ish cuff. Now, if you have shorter legs, muscular calves or stalkier legs then the cuff won't be the best look for you. It will definitely shorten your legs visually.

Now, if you have ankle length jeans then no cuffing is required! These are jeans where the length is a bit shorter -- hitting around the top of the ankle bone (NOT to be confused with capri jeans. Which none of you should be wearing. Not one single reader).

If your booties have a longer shaft -- the top of the boot hits several inches above the ankle bone -- then it just got a bit trickier. You will see a million different options here. Honestly, I don't think many look very good on me so I generally just avoid this style boot. I don't care to fight that battle. Unless, I wear them with leggings, tights or ankle jeans since they skim just the top of some boots. Here are my preferred options for a higher cut bootie:

The single cuff

Although, you can certainly roll your jeans or even do one smaller cuff. It gets simplified when paired with an ankle or cropped length jean or leggings:

On the left: Ankle length black jeans that barely skims the top of the booties. On the right: Black leggings that fall nicely inside the bootie.

And there you have it! A couple options to get you started on getting your jeans and booties paired up right. This isn't an exhaustive or definitive list. However, this should get you feeling pretty good to go or take care of the issue altogether. Be free of your anxiety on this topic and save that for bigger issues. Like potty training the kids, house training the puppy or what the heck is going to happen to Steven Avery?!

#fashion #Howtodostylingtricks #wardrobeconsultant #Styling #AmazingGray #fashionblogger #blog #falltrends #personalstylist #personalshopper #Tallahassee #Howtowearankleboots #anklebootsandjeans


Amazing Gray Personal Styling  |   angie@amazinggraystyle.com  |   850-591-0893