Everything You Need to Know About Styling Jeans and Boots

As we head into fall, boots and booties start to show up on our radar.  With the many different styles of jeans currently trending, I started wondering how to style jeans and boots.  After a little research, I’ve come up with a few perfect solutions for us.  After all, just because most of us here are over fifty, it doesn’t mean we don’t want to be stylish.  

For those of you who are new here, I call my style “modern classic”—and I know a lot of my peers call their style “modern classic” as well, but here at Sharing A Journey, I mean that we blend classic style  with modern pieces.  We go for contemporary fit and add a trend or accent piece here or there to make the look our own.  We shop at a variety of shops to create our own personal style, rather than purchasing ready made outfits.  I wanted to share that philosophy so you can feel free to create outfits according to your personal preference.  So back to styling jeans and boots.

When everyone was doing skinny jeans, the jeans and boots situation  was pretty straight forward:  Skinny jeans went with most types of boots.  However with all jeans styles currently trending, it becomes trickier.  For example, flair jeans won’t fit into a knee high or over the knee boot—you will have fabric blousing out of the top of your boot- or worse bunched up inside the shaft of the boot, but flairs look amazing with a pointed sock boots.  So what needs to happen first, is that you need to figure out which jeans are best for you, and go from there.  I’ve written about choosing jeans here. 

Once you’ve sorted out which types of jeans you like, then you can begin to accessorize them with the right boots.  The best part of this exercise is that there is something for everyone, unless you don’t wear jeans.  However, these same ideas will also go for trousers and pants,—I’m here to help  everyone, as you can see.

Let’s have a quick chat about jeans shall we?  We all know the skinny jean, it is skin tight and tapers at the ankle.  The skinny also comes in a cropped version which shows off our super cute ankle bones.  And then there is the boot cut jean, some times called a straight leg,  the cut is long, and straight.  It’s not as form fitting as the skinny—especially at the calves. One of the most important thing to note with a boot cut jean is the length.  It looks a bit odd if it’s not the right length.  

These Booties are Hot

If you want to add a little pizazz to your wardrobe this season, and enjoy a trending look for seasons to come, start with a great pair of booties. For the trend lover, I selected these lug sole booties in a light beige. They will look great with cropped styles, skinny jeans and peaking out from a pair of flairs. I had a pair in black–they somehow ended up in my daughter’s wardrobe-they are that good and comfortable too. My personal favorite are the square toe booties–not too high a heel but really high on elegant style. For the final look,( I have a pair like these in red, and I wear them through fall and winter). Shown in black, these stack heel booties are a wardrobe staple.

My favorite, flair jeans are also trending this year.  Flairs should be long enough to just brush the floor.  I love flairs because they elongate the silhouette and make you look as if you have long legs.  

As you can see, there are many different styles and they need be worn in different ways. I’m sharing here the best ways to style jeans and boots by jean type.  I figured the easily way to be helpful, since you can scan down to the type of jeans you like to wear—I’ve pared the boots with the jeans along with a few notes on styling and this year’s trends.  It’s simple, you choose the pair of jeans and pair of boots that look best and you are good to go.

Speaking of which, along with the classic styles we all know and love, we are seeing combat boots, “track sole” boots and hiking boots this season as well as a re-emergence of the sock boot and some variations of the cowboy boot.  Snake skin, and leather are showing up more this season—and so far, I’m seeing less suede than in seasons past.  Mind you, that doesn’t mean I won’t be wearing my suede boots—my policy is that I wear what I love even if its not on trend.  I blend it with things that are trending—that’s part of that “modern classic” thing we talked about before.  

When starting your boot wardrobe, I think you need a variety of different styles and colors in your boot collection.  You will want black boots-they go with most neutral colors, and brown boots, for casual wear. I also think it’s important to have a pair of dress boots that can be worn with jeans, skirts and dresses.  This season, there are many boot styles to choose from, which is good news.  In any event, with this post, you will be able to figure out the best option for you and your body type.

Boot Cut Jeans and Straight leg jeans:

Second to flairs, I love a good boot ut or straight leg jean.  I thing they are very flattering, especially with the higher rise we have been seeing these past couple of seasons.  This type of jean is versatile when it comes to wearing boots because you can tuck them into a knee high boot, specially if you get a slim fit.  They  as well as wearing them with  this season’s cute booties.  If you choose a relaxed fit, you might have trouble with the fabric pooching a the top of the boots.  If this happens, you can simply choose a different kind of jeans or switch to booties.

Booties:  When choosing booties to wear with straight leg jeans, consider trying the cropped cowboy bootie perhaps in python for added interest.  A sock bootie can also be worn with just the pointed toe peaking out-  this is where the length of the jean is important.  

Chelsea Boots are a classic and come in a variety of heel heights.  I am often asked for suggestions for stylish low heel options, and the Chelsea boot is a great low heel option.  

Skinny Jeans are a staple in most of our wardrobes and are great for styling boots, especially knee high and over the knee boots.  I love styling a tunic with skinny jeans and a cute pair of over the knee boots, though we have been seeing fewer over the knee looks over the past couple of years.  I did’t wear mine at all last year, and have been looking to add knee high boots to my collection this year and going forward.  

Since there are so many boots to experiment this year, why not try a pair of track sole boots or a pair of combat boots to freshen your skinny jean look.

Flair jeans, as I have shared are my favorite in the jean family, but, they are probably the least boot friendly of all the jean styles.  I love wearing my flair jeans with pointed toe booties, especially sock booties.  I will also go for a pair offtrack sole boots, as flairs look great with interesting toe and heel details, as well as interesting leathers and patterns.

Wide Leg Jeans fall into the category similar to flair jeans as the additional fabric makes them challenging to tuck into boots.  Here as with flairs, I would focus on booties with interesting patterns, materials, toe and heel details.  If you are interested in trends, you may try combat boots, hiking or track sole boots.  

We are seeing a variety of cropped jeans, some are tapered, while others are belled at the ankle.  These jeans scream for a bootie that shows off a little skin between the top of the boot and the jean.  We are seeing raw hems, which are meant to be shown off-so be sure to really pay attention to the height of the boot and the length of the pant.  A finger’s width of skin should show so your boots take center stage.  The boots that look best with cropped jeans are:

Chelsea boots

Sock boots

Lace Up boots

Track Sole or (lug sole) Boots

Some people ask how to choose the right boot and jeans colors—white jeans look great with a neutral color like light beige, soft grey or black boots.  Dark blue jeans look great with all colors of boots-as do black jeans. 

I have blended in this season’s trends into each jeans grouping, but I thought I’d cover them separately- but before I do, I want to share my view on trends.  I love a smattering of trends in a wardrobe-and purchase trends when they really sing to me. Occasionally I will purchase a trend from a discount retailer if I am interested but feel like it’s going to go out of style quickly.  However, if I love the item, I will invest and consider it an accent piece even if it isn’t continuing to trend.

Track sole boots have a thick tread, rounded toe and sit just above the ankle, my daughter bought a pair a few years ago, and then gave them on to me.  I gave them away last year, and wouldn’t you know they are back!  These look great with boot cut jeans, crops and skinny jeans.  They are great for those of you who like an edgy look.

Lace up boots: These boots remind me of what we used to call witches boots, they are very delicate, sport a heel, and lace up the front.  These would look amazing with a pair of cropped jeans-perfect to show off the details of this type of boot.

Sock booties are back as well, though this time they are being shown in leather. They are delicate, with kitten heels, great for the glamorous fashionistas out there.  These look great peaking out from a pair of flairs as well as going well with all jeans styles.  

Combat Boots returned a couple of seasons ago, and I think they are here to stay for a while.  They look great with straight legs and skinny jeans.  If you aren’t completely sold on combat boots, you may want to check out hiking boots which you will see more of this season.

One of the best things about boots is that they look great on everyone, and they can really make an average jeans outfit sing.  I’d love to hear which boots you are wearing this season.