Learning from Pinterest: Boots + Jeans

I was always a bootcut jeans girl, so figuring out how to wear boots with my jeans was pretty darn easy. Put on jeans + stick boots under jeans = done. Easy peasy.

Over the past year, I’ve started liking more of the straight and skinny jeans styles. In the summer, it’s pretty easy to style them with Toms, flats or sandals… but once the weather started getting cold I was kind of at a loss.

Most of my jeans weren’t super tight at the ankles, so shoving them into the tops of my boots looked kind of odd to me. If I rolled them up, that looked kind of weird too. I know that other people seemed to figure this out easily, so I’m not really sure what my issue was.

So I did what every lady does in 2014… I checked Pinterest. You can check out my Wearing Jeans + Boots board here.

It seemed like there were three main ways of dealing with things:
1. Shoving the pants inside the boot.
2. Cuffing the jeans above the boot.
3. Wearing boot socks.

In the name of science, I decided to try them all out. I mean, I might as well do the work so you don’t have to, right?

Here are the pants I was working with: Kayla Skinny Jeans in Red (from this Stitch Fix post), Kate Spade Broom St Grey Denim Skinny Jeans (Nordstrom Rack), Kut from the Cloth Toothpick Skinny Jeans (Nordstrom Rack), and Kensie Sophia Distressed Jeans (from this Stitch Fix post).

I picked these four pairs of pants because they get the most wear out of my closet. The Kensie jeans are pretty tight at the ankle, which makes them easier to manipulate into boots, but the others are more of a straight bottom which can make things awkward.

Here are my favorite boots that I’ll be using to try each style:

boots - Pocketful of Joules

A. Naturalizer Jovana boot – a pretty typical knee-high version.
B. Nine West short boot – a bit shorter, which can make them hard to style.
C. Cole Haan Air Tantivy boot – a medium height, which can be awkward.
D. Frye Wyatt Disk short boot – more of a “bootie” look.

Why yes, that is a pair of FRYES in my boot list! After I lucked out in Austin last week I went ahead and clicked ‘buy it now’ on a pair I was stalking on eBay. They go for $350 new, but I got them for $99! YAY for being patient and stalking shoes online!

Style #1: Shoving the pants inside the boot.
So when I first thought of how to throw on a pair of boots with skinny jeans, I figured I’d just shove those bad boys in there. In order to keep them inside the boots, there are a few Pinterest tips that can help: you can do a small roll of your jeans and then shove that into the boot, you can tuck your jeans into your short socks, or you can buy little straps that connect to your jean cuffs and go under your foot to hold them tight.

Style one - shoving the pants inside the boots.

So this style seems to depend on the pants and the boot height. For the first picture it’s working with the mid-height Cole Haan boots, but looks a little stumpy. I think that the higher knee-high boots would look much more flattering. The grey jeans are not very tight at the bottom, so they look a bit sloppy stuffed into the Fryes. As for the distressed jeans and grey Nine West boots, this is how I typically wear them. Since they are pretty fitted at the ankle, it’s easy to stuff them inside the boot.

Style #2: Cuffing the jeans above the boot.
It seems that many people deal with the weird shoving the jeans in the boot issue by cuffing their jeans above their boots, showing off either skin or cute socks. Here’s an example pin with socks and one without socks.

Style two - cuffing jeans above boot

Ok, the red jeans are a mess. They are just too baggy to cuff above the boot and it looks pretty ridiculous. I’m also not loving the dark blue jeans cuffed — it’s not terrible and I’d probably leave the house like this, but something about the bulkiness of the cuff isn’t doing it for me. The only one that’s really working for me is the skinny distressed jeans. I actually like the look of the cuff with a pair of neutral socks peeking out.

Style #3: Wearing boot socks.
Apparently boot socks are all the rage and you can totally buy them at department stores, specialty stores and on etsy. Or, you can make your own using thrift store sweaters or old socks. I bought a couple $3 sweaters from my local Goodwill to try this out myself.

Style three - wearing boot socks

Now this is a style I can totally get behind, because it seems to work well with my tall boots and my medium-height boots. All I did was take a couple sweaters and cut the sleeves off! The boot socks do double duty of keeping my legs extra warm and also looking pretty darn cute. I’m thinking a sparkly sweater cuff could look snazzy peeking out for the holidays. Or, you could sew on a pretty button or pin on a jeweled broach. A little tip, when you’re buying thrift sweaters to use… go for a medium or a large. Both of the ones I bought were size small and I think the cream pair would look better if they weren’t stretched so tight.

I’m really glad I tried this little exercise because it helped me figure out how to mix and match boots and pants from my own closet, without going on a shopping spree for jeans with tighter ankles. So, get used to seeing me in lots of jeans and boots this winter!

Am I the only one who had issues with the whole boots and jeans combo? Did you find my examples helpful at all? Do you have a boots + jeans tip I should try?

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8 thoughts on “Learning from Pinterest: Boots + Jeans”

  1. I totally feel your pain. All of my boots are short. Either ankle or a few inches above. I even have this issue with my snow boots. If I put my pants over the boots, my cuffs get wet, if I shove them in the boots they look stupid. Leggins are the exception to the rule because they tend to look adorable with ankle boots. I like the look of the socks but you’d have to have boots loose enough to fit not only your leg but the pants and socks. That can be tricky if you have bigger calves in a knee high boot. Which I do.

    1. I have an awful time finding knee high boots because apparently I have Hulk calves. The ones I finally found are “wide shaft” and actually even have room for jeans AND socks!!

  2. I totally love your boot socks and would rock that like crazy! I always have a hard time finding boots to fit my calves, though. I think I’ll end up with shorter booties, and then what shall I do? Ack!

    1. I have a hard time finding knee high boots too, but the ones I’m wearing are a “wide calf” style that are awesome. Try googling the brand — they might work for you too!

      Also, boot socks can be worn with short boots too! 🙂

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