Expert Advice

How to Wear Boots this Fall & Winter

By on 08/31/2022

Let’s talk boots! Fall and Winter are just around the corner, so it is time to break out those cute and stylish boots. There are so many to choose from, so we recommend starting soon! Get started on your fall and winter boot collections here!

How to wear ankle boots

Ankle boots can be styled in many different ways no matter what your age. Dress them up and you can dress them down. Use your boots to make a fashion statement by going with a bold color/pattern, or you can go for a more neutral/muted tone. Pair them with a bulky biker jacket, or just a classic white T-shirt. There are plenty of variations to try when it comes to ankle boots for women.

How to wear ankle boots with jeans

If you are looking for a more casual look for your ankle boots, jeans are a good route. Skinny jeans are most recommended for these types of boots. If you are wearing them with skinny jeans that are cuffed, tucked in, rolled under, or with a pair of jeans that hits at the ankle- you are good to go!

How to wear straight leg jeans with ankle boots

Straight leg jeans have a slight leg opening to them and sometimes pairing them with ankle boots can be tricky. No worries, to pull this look off all you need is a snug ankle boot. This allows for the straight leg jeans to fall right over the top of the ankle boot. Another look to spice up your straight leg jean and ankle boot combo is adding some flare with platform ankle boots!

How to wear boots with jeans men

There are a few different ways for men to style their boots with jeans. The three simplest ways to go; tuck them into your boots, cuff them to compliment your boots, or stack your jeans. Tucking your jeans into your boots is quite simple- just tuck your jeans in! With this we recommend wearing a slim-fit pair of jeans for this look. Cuffing your jeans is meant for more of a straight-leg/ looser-fitting pair of jeans. What you are going to want to do is simply grab 1-2 inches of the bottom of your jeans and rolling them, so they sit just at the top of your boot. The last style, stacking your jeans, is best paired with an ankle boot or a mid-calf boot. Pull the bottom of your jeans up around the top of your boots and you’re done!

How to wear and style boots men

Dress them up or dress them down- there are boots for every occasion. Men can wear boots for the office, field, or casual wear- you name it! Style them with a pair of slim or loose jeans, dress pants, shorts, etc. When it comes to boots, the opportunities are endless.

How to wear and style Chelsea boots

Chelsea boots for women are very versatile. Dress them down with jeans and a T-shirt or up with a suit or dress. For the perfect look make sure the leg of your pant sits just over the top of your boots. You can choose either a brown or black Chelsea boot depending on what will work best for your outfit. Chelsea boots come in both suede and leather. Chose the suede style for a more casual look and leather style for a more dressed-up look.  

How to wear Chelsea boots men

Men’s Chelsea boots have rapidly grown to be a statement piece in every guy’s wardrobe. Whether it is a cold winter day or a casual event – Chelsea boots are the ultimate shoe for versatility. Wear them with jeans, suit, winter coat, the choices are endless. These boots will be your new go-to.

How to wear and style Combat boots

Wear and style all your fall outfits with women’s combat boots – or even better, platform combat boots! For the more rugged look, combat boots are perfect for any fall outfit. Pair them with a slouchy sock for any casual event.

How to wear black combat boots men

A pair of men’s black combat boots is a must for every guy’s wardrobe. They are easy to style and go with so many different looks. Wear them with a smart suit for the office or in a more relaxed setting – combat boots are good for most occasions.

How to wear and style Cowboy Boots

When it comes to men’s cowboy boots and women’s cowgirl boots, everyone needs a pair. The country style is one of the most trending looks out there. Cowboy boots go with dresses, jeans, skirts, you name it. With a good pair of mid-calf boots will take you from the dance floor to dinner. Not to mention, there are many different styles of these boots. The first thing you must do is know what you will be wearing these boots for, and then from there you can choose a material to your boot. Some popular materials are alligator, cowhide, ostrich, and snakeskin.

How to wear and style white boots

From women’s white boots to white platform boots to white knee-high boots to white ankle boots – own and rock them all! With all these variations of white boots, you can’t go wrong when picking an outfit to wear them with. You can even try a pair of white boots for a fall wedding guest dresses with boots look! Men’s white boots are great options for men who want a more fresh, classy, and clean look!

How to wear and style Knee High Boots

The answer is simple- wear and style knee high boots with a sweater dress. You can’t go wrong with tan knee high boots or leather knee high boots to complete fall dress outfits with boots! For those that need a little extra room wide calf knee high boots are great and are available right here on ShoeMall!

How to wear and style hiking boots

Hiking boots are not just for hiking anymore. Grab a pair of men’s Merrell hiking boots, or Bearpaw women’s hiking boots and a flannel shirt and hit the trail or go out for a casual day.

How to wear boots with jeans

A pair of my favorite fall boots with jeans is my go-to in fall! Here are three easy & simple ways to style your boots with jeans.

  1. Tuck your jeans into your boots. This works best with skinny jeans.
  2. Cuff your jeans to show off your boots.
  3. Hide your boots under your hems.

How to wear cowboy boots with a dress

Short-sleeve, long-sleeve, strapless, or fall dresses with cowboy boots – any dress goes perfect with a pair! We highly recommend a denim style dress to wear with cowboy boots. Otherwise, white or floral embroidered dresses completes the style. Shop our women’s cowgirl boots to find the perfect boots to wear with your new trending look!

How to wear boot socks

Looking for a pair of cozy and comfy socks to wear with your boots? Boot socks are the way to go! The most typical type of boot sock is a knitted style. We highly recommend boot socks to wear with your boots during the cold months for a cozy look and feel. Choosing the color to your boot socks can make or break the outfit. Wearing a color that matches the boots, or even choosing a statement sock is most recommended.

How to wear tights with dresses and boots

Add a little extra warmth to your fall/winter dress with tights. Tights can be styled with many kinds of boots, but there are a couple rules of thumb to follow. Try your best to match your tights to the color of your boots, stray away from ankle boots with tights and a dress, and lean more towards a dress with sleeves.

How to wear a sweater dress with boots

There is only one answer to this question- thigh-high boots! If your sweater dress is above the knee in length, then thigh-high boots are the absolute way to go. These boots will be having you looking stylish, but also keeping you warm during the fall and winter months.

What’s your must-have boots for this fall season? Let us know in the comments below, and be sure to tag us in your first fall boot looks on FacebookInstagram, and Pinterest!

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