Building Chic Winter Looks with Jeans

Casual Attire

When it comes to casual dressing, jeans are arguably the first piece most of us reach for. But what about the rest of our look?

With that question in mind, I thought that a tutorial on putting your jean looks together was in order. Not only will you find the information fun, but it will also be endlessly useful! 

In this post, we will look at three jean styles: wide-leg, skinny, and bootcut. I’m not including cropped silhouettes as we’re dressing for colder weather right now, so we’ll keep our jean lengths long. That said, in this week’s shopping, I’ve included jean styles in each category (in case it’s time to add to your jean wardrobe), along with various boots, shoes, and some yummy sweaters to help create your jean looks. I’ll also discuss the necessary details to pull some fabulous looks together.

So, without further ado, let’s begin!

Styling Wide-leg Jeans  

You will see more shoes here than in the other two categories, where I focused almost entirely on boots. Note the mules, clogs, ballet flats, and especially the smoking slippers—an all-time favorite of mine. 

All of these shoes are adorable and perfect for year-round easy dressing. And in the boot category, you will see lots of chunky and lug-sole boots that will pop your wide-leg jean look. This is not to say the shoe categories won’t pop your look, as they do, just differently.

There is one style of boot that I’ve been unable to find this season, and that is the pointy-toed flat boot. I bring it up because I want you to make a mental note to watch for this silhouette. You will see some very low-heeled pointy-toed boots as they work beautifully with the wide leg but remember to keep any pointy toes as low to the ground as possible.

In the sweater category, you will note a few cropped cardigans that will look adorable with a T-shirt under them. When it comes to wide-leg jeans, you can do almost any length or fit of sweater. For instance, a fitted turtleneck is gorgeous if your tummy is flat. Throw a jacket or coat over it, and you are good to go. 

The tunic sweaters featured in this post are a bit lighter in weight, and that is because my intent is for you to tuck a section of it in the front and let the rest of the sweater drape. A few sweaters are designed to drape at the waist and are also fabulous with the wide-leg jean.

You might be wondering about a third piece, and you can do anything from a denim jacket in more temperate zones to a mid-length (just below the knee) puffer. A shearling jacket is also perfect—and it doesn’t matter if the cut is cropped and you have a layer hanging out. For instance, if you do the tunic sweater tucked in the front with the rest of the hem hanging out. The layers give dimension to your look, and it’s so chic. Of course, the longer jacket works beautifully here, too. 

There is lots of fun to be had styling your wide-leg jeans, considering the large variety of pairings you can do. 

Styling Skinny Jeans

Most of us have kept our skinny jeans to use as leggings of sorts for our taller boots. For that reason, I have shopped a number of them for you, including some fabulous brands at equally fabulous (low) prices.

You will also see mid-calf to over-the-knee boots and everything from flat to heeled boots. One thing to note—and this is counsel that you will always want to keep in mind when styling skinny jeans—do NOT wear ankle booties with your skinny jeans. The only exception to this rule is if you can pull your jeans out over your boots and the boots are pointy-toed. Otherwise, stick with the tried and true and oh-so-flattering plan we show here. The offerings here are delicious and can easily be combined to create the compliment-garnering looks you prefer.

I mainly stuck with tunic sweaters here as they are lengthening and slenderizing—and who doesn’t love that? You can do the tuck-in thing in the front with your sweater, which adds dimension to your look and also helps to slenderize. This fabulous look is so easy to pull together.

As for your third piece, I recommend the same looks mentioned in the wide-leg jean section.

Though skinny jeans have taken a backseat in the denim world, they are ever so useful when you want to tuck them into your boots.



Styling Bootcut or Flare-leg Jeans

Lastly, I’ll focus on the silhouette that is flattering to everybody—literally! I’m talking about bootcut or flare-leg jeans. These jeans make you look long and slender and are just plain fabulous! You will see some great brands and variations here; they are absolutely dreamy!

With regard to the footwear, I’ve broken it down into two categories—pointy-toed boots and chunkier boots, some of which are lug-soled. I have also included a few pointy-toed mules, which I am absolutely possessed by! And the best part is that each one of the styles featured in this post can change up your look entirely. How fun and simple is that? Change your shoe or boot and change your entire look! I love it!

The sweaters I’ve shopped for this section range from shorter/cropped to sitting on the waist to tunic length. Like the shoes mentioned in the last paragraph, with this style of jean you can vary your look tremendously by varying the length of your sweater.

I am a huge fan of the tunic as it comes down longer to sit below your backside, and the dimension adds length, especially when you wear a pointy-toed boot or mule. It’s a wow combination, and if you tend toward rounder hips, this is a winner. I do not have rounder hips, and it’s still my favorite as I love this silhouette for its lengthening and slenderizing properties.

For your third piece, you’ll once again want to layer your longer sweater with a shorter jacket—whether it be shearling, denim, or a puffer. This works beautifully. If you choose a puffer that comes just above or at your knee, you will further emphasize the lengthening effect—and it is a serious WOW!


Summing it all up…

While I didn’t shop any third pieces for this post, you can easily revisit our blog, Cozy, Chic Winter Wear for the City and Mountain Resorts, in which we highlighted winter jackets that can serve as gorgeous third-piece solutions. That article includes shearlings and puffers, so it will definitely come in handy as you create your fabulous jean looks.

I hope you have so much fun as you peruse the categories of our favorite casual apparel item… the jean. And here’s to achieving the chic we all strive for quickly and easily! Happy shopping—and dressing!

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