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How to Wear Jeans and Shoes

I just realized, after I had prepared this post, that I have been writing a lot about how to wear jeans and shoes. I showed you some cute ways to wear converse and how to wear ballet flats! (There’s still time to enter to win $250!) However, there are a lot of other options out there! What type of jeans do I wear with my booties? Do I one cuff or two cuff my jeans with flats? What type of jeans go best with a combat bootie?

Well, I’m here to help!

I do believe there are multiple options when it comes to how to wear jeans and shoes, and although there are some hard and fast rules, as long as you’re not breaking those, you’re probably fine. Let’s get started!

How to wear jeans and shoes

how to wear jeans and shoes

So our basic shoe choices are flats, heels, booties, combat boots and riding boots. Most shoes can fit into those categories.We’ll start with flats and work our way up!

Jeans and Shoes: Flats

how to wear jeans and shoes - ballet flats

When I showed you ballet flats with jeans the other day, I showed them with two, thick cuffs. Today I’m showing you a thin one-cuff. Just enough to show the cuff and a little ankle but no need to cuff it up more. These particular ‘jeans’ are actually jeggings. So they are tight but still cuff-able (is that a word?) at the bottom. Not to mention extremely comfortable!

Jeans and shoes: Combat booties

how to wear jeans and shoes - combat booties

Those shoes are the best. They go with me everywhere. They’re cute and they go with pretty much everything. I’ve worn them so much they are even starting to come apart at the toe! No worries, I will just repair and keep it moving. Combat boots can be tough to style as well. They come up high, but don’t look right under a boot cut jean. Skinny jeans can’t go over them, what’s a girl to do?

With jeans and combat boots you have a couple choices. You can tuck your jeans into the boots, tuck them into socks and then the boots and you can also cuff them like I’ve done here. I did a post a while back with a bunch of ways to wear combat boots as well as ankle boots, you can check that out for more inspiration!

Jeans and shoes: Riding Boots

how to wear jeans and riding boots

There is really only one way to wear jeans and riding boots – with super skinny jeans. Boyfriend jeans, straight-leg jeans, or really anything else doesn’t work. These boots are meant to go over your jeans and not have a lot of material bunched around the knee. So pair these with your skinniest of skinnies or even leggings 100% of the time.

Jeans and Shoes: Boot Cut

how to wear boot cut jeans with shoes

Boot cut jeans can be tricky as well. They are meant to go over boots (hence the name) but definitely look better with a heel. Thats why these are great paired with a wedge. Definitely make sure that your jeans are long enough. Not a good look when you’re wearing a heel with a pair of boot cut jeans that don’t hit the shoe.

Jeans and Shoes: Leggings with a Bootie

leggings with booties

These are those same jeggings as above that I one-cuffed. Here I just did a simple, thin two-cuff to pair with some low ankle booties. It works because you are showing skin between the boots and jeans and the cuff adds style.

Jeans and Shoes: Skinny Jeans & Booties

Booties with skinny jeans

I wear these a lot. They are so comfortable and so cute – what more is a girl to ask for? They look great double cuffed, but I wanted to showcase the single thick cuff. Just another option when pairing jeans and shoes! Other options would be double thin cuff or double thick cuff. What not to do with these types of booties is try to wear a skinny or straight-leg jean over the boot. It will just look funny. If you have ankle boots with a heel that will fit comfortably under your boot cut jeans (mine don’t) then that works too!

Jeans and shoes: heels

How to wear jeans and heels

I don’t think you can really go wrong with a pair of heels. They make every outfit super cute. They go well with boyfriend jeans, boot cut, skinnies, even leggings! I paired them here with a pair of my skinnier jeans without any cuff. You can cuff your jeans with heels, but I preferred them un-cuffed.

Well, there you have it! Seven ways to wear jeans and shoes. There are obviously more options than these but if you just stay away from the no-nos, you’re probably okay.

Any other suggestions? How do you wear jeans and shoes?


4 Responses to How to Wear Jeans and Shoes

  1. Cate @ Wild Ruffle April 8, 2015 at 6:45 am #

    Ooh – love those combats! Some great tips. 🙂

  2. Darcy April 8, 2015 at 7:10 am #

    So many great shoes! Love those cutout booties!

    • Natalia April 8, 2015 at 8:26 am #

      Thank you! Those are some of my favorites too!

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