Wide-leg jeans aren't going anywhere, and honestly, I don't think they should. I love them so much (welcome back my teenage years!) They're comfortable, flattering, and one of the easiest pieces to make an outfit look effortlessly put together.
But when winter arrives, finding the right boots to wear underneath them can get a little tricky.
Some boots disappear under the denim. Others add too much bulk. And then there are those combinations that somehow make an otherwise great outfit feel a little off.
If you've ever stood in front of your closet wondering which boots actually work with your favorite wide-leg jeans, I've rounded up four winter boot styles that get the proportions right while keeping your outfits comfortable, polished, and stylish.
Here are the winter boots I'll be wearing with wide-leg jeans this season.
The Sleek Chelsea Boot
Best for: Everyday outfits and a polished, effortless look
A classic Chelsea boot is one of the easiest boots to wear with wide-leg denim. Its streamlined shape keeps the outfit from looking too heavy, especially when you're wearing a fuller-leg jean.
Look for a boot with a slightly pointed or almond-shaped toe and a modest platform or heel. A chunky lug sole can work, too, but I prefer something that doesn't compete with the volume of the jeans.
I love Thursday Boot Company’s Chelsea boots because they are just a touch edgy. They’re a little bit rugged, a little bit polished, I feel like they show my personality pretty good.
How I'd wear it: Dark-wash wide-leg jeans, a cream sweater, a wool coat, a simple leather crossbody.
Cold days, cozy layers, and a really good pair of jeans. Winter style at its simplest.
The Suede Ankle Boot
Best for: Adding texture and a little European-inspired style
If there's one boot that makes a winter outfit feel a little more elevated, it's suede.
A chocolate brown, or taupe suede ankle boot looks beautiful with denim. The softer texture adds interest without making the outfit feel overly styled.
Choose a boot with a pointed or almond toe and a slim profile. A little heel is especially nice with wide-leg jeans because it helps the denim fall beautifully.
How I'd wear it: Medium-wash wide-leg jeans, a soft neutral knit, and a brown suede ankle boot.
Make sure you pre-treat the suede and wipe any snow off after your done wearing.
The Warm Winter Snow Boot
Best for: Cold, snowy days when warmth comes first
When it is really cold out, style doesn’t always have to go out the window. But warmth comes first when it is really cold.
I grew up in northern Canada. I know cold, like -48 C cold. The brand that I swear by, my mom swears by and all my siblings. Sorel. Every time. Sorel is stylish and warm.
If you are out and about in the city and need warm, I would layer thermal leggings underneath my wide leg jeans.
How I'd wear it: Wide-leg denim, a chunky cream sweater, a long wool coat, and Sorel boots. Sometimes the wide leg will work, sometimes, you need more of a skinny jean to tuck into for warmth.
Skinny jeans for your winter boots is still so cute. Practical over trendy for warmth.
The Waterproof Chelsea or Winter Ankle Boot
Best for: Rainy, snowy days when you still want to look stylish
Not every winter day calls for a beautiful suede boot. Sometimes you need something that can handle actual weather.
A waterproof Chelsea boot is a practical choice that can still look great with wide-leg jeans.
Look for a streamlined shape, a comfortable sole, and a shaft that fits neatly underneath your denim. I love the look of a lace up chelsea too, its a bit edgy and reminds me of the 90’s.
One thing to remember: make sure your jeans don't drag on the ground or sit in wet snow. A slightly shorter wide-leg hem works particularly well with winter boots.
How I'd wear it: Cropped wide-leg denim, a chunky knit, and a waterproof leather boot.
A Few Styling Rules That Make All the Difference
Before you buy another pair of winter boots, there are a few things worth remembering when pairing them with wide-leg jeans.
1. Pay attention to your hemline.
Your jeans should skim the top of your boot without dragging on the ground. A little heel can help create a longer, more flattering line.
2. Don't be afraid of a pointed toe.
Even if most of the boot is hidden, a pointed or almond-shaped toe adds a little refinement underneath wide-leg denim.
3. Watch the proportions.
A very wide jean paired with an extremely chunky boot can sometimes feel overwhelming. Balance the volume with a more streamlined shoe.
4. Choose your colors thoughtfully.
Chocolate brown, black, cognac, and taupe are all beautiful winter boot colors. They also make it easy to build outfits around the denim and sweaters you already own.
5. Let the boots complement the jeans.
The boots don't need to be the statement piece. Sometimes the simplest combination is the one that looks the most expensive.
And if you are at a loss and can only afford 1 pair of boots, you can never go wrong with a gorgeous, cozy pair of Uggs. Just treat them first.
You are going to want to invest the most in the boot which is the most appropriate for the weather you live in most of the time. I know that sounds obvious, but I live down in the desert now and want so bad to buy the beautiful Sorel boots, but I just do not need them anymore.
You want to love wearing your boots, not just love looking at them in your closet. Buy for the winters you actually experience, not the winter wardrobe you wish you had!
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