how to wear chelsea boots

Some things easily stand the test of time. When it comes to footwear, Chelsea boots are the perfect example. The reasons are obvious. They can be worn on any occasion, suit various types of outfits, and can withstand any season. They are thus a practical yet stylish choice for both men and women. You can wear them with black leggings, jeans and socks, mini dresses, skirts, blazers, and more.

Chelsea boots are a product of British heritage. Today, they are worn all over the US, being a staple in many people’s wardrobe. However, sometimes, we feel stuck when it comes to styling them. If you are currently facing this situation, this post is for you. Keep reading as we tell you all the different ways to wear Chelsea boots.

Must Read: How to Wear a Sling Bag

What Do You Wear With Chelsea Boots?

Chelsea boots can be worn with an array of outfits. But they look especially good in certain types of clothing compared to others. Here’s a round-up of some of the best boot outfit options.

Black Leggings

Black Leggings

Perhaps nothing suits Chelsea boots as well as black leggings. It’s the perfect winter outfit for a fashionista. If it’s really cold, wear boots with a sock for added warmth. If you want to create a color-blocked look, opt for a pair of two-toned Chelsea boots.

If, on the other hand, you desire a sporty look, opt for printed or black-and-white leggings. You can pair the leggings with a leather jacket, hoodie, tee, or sweatshirt.

Jeans and Socks

For an effortlessly casual look, pairing Chelsea boots with faded or distressed jeans is the way to go. Roll up the cuff of your jeans slightly to show off the boots. For the upper half, hoodies and T-shirts are great choices. If it’s summer, pair the boots with jeans and a light denim jacket or tank top.

For a more laid-back look, pair Chelsea boots with a pair of wide-leg jeans.  It will put your boots on full display while also making you look stylish.

Mini Dress

Calf-length Chelsea boots with mini-dresses are a killer combination. The dress can be printed or plain. Wearing a shining black leather jacket with the dress will take your look up by several notches. Mini dresses also look good with low-heeled Chelsea boots. Again, throwing a black shearling jacket will make you look smarter.

Skirts

Skirts

Several types of skirts look good with Chelsea boots. Here are 3 types of skirts that you can experiment with.

  • Pencil skirt: A pencil skirt with Chelsea boots gives a minimalist yet stylish look. The straight and tight fit of the skirt accentuates the look of the shoes. You can even wear it in winter with long socks or stockings.
  • Tube skirt: A tube skirt narrows from the bottom. You can pair it with a fitted top that tucks into the skirt. Then, slip on your pair of Chelsea boots to look like a style diva.
  • Suede skirt: Brown and grey suede skirts are always trending and versatile. Suede skirts can be worn with a cropped sweater, neutral shirt, or sleeveless top. All of these combinations look great with Chelsea boots.

Blazer

Chelsea boots with blazers can be a formal or informal outfit, depending on your choice. There are a multitude of looks that you can rock.

  • For a relaxed ensemble, team a blazer with light blue boyfriend jeans. Chelsea boots will fabulously complement your outfit.
  • A blazer with black skinny pants is a comfy and stylish ensemble. When paired with a pair of Chelsea boots, they make the outfit look more relaxed.
  • A blazer and black leather leggings give an off-duty vibe. Chelsea boots instantly bring the entire outfit together.
  • This combination of a blazer and a black leather mini skirt makes up for a stylish casual outfit. When worn with Chelsea boots, it instantly bumps up your look.
  • A blazer with ankle-length pants and Chelsea boots looks highly professional. It is ideal for formal occasions.

Sweater and Tights

Sweater and Tights

Sweater, tights, and Chelsea boots make up for an elegant ensemble, perfect for almost any occasion. Try out these combinations.

  • A striped turtleneck sweater with tights is a great casual outfit. Pair it with Chelsea boots to polish the look further.
  • A Black V-neck sweater with tights and Chelsea boots is another smart and stylish ensemble.
  • Chelsea boots also look stunning when paired with a sweater dress. We recommend opting for a dress in neutral colors, such as black and white.

Shorts

Chelsea boots look great with denim or jean shorts, as well as leather shorts. If the weather’s cold, pair the shorts and Chelsea boots with a knit sweater and sheer tights. If it’s hot, pair the boots up with a crop top.

One of the sweaters that compliment Chelsea boots and shorts is one with a turtleneck. Another great option is to pair brightly colored shorts with black and white horizontal striped shorts. Here are some other combinations to try.

  • Brown coat, shorts, and black Chelsea boots.
  • White long-sleeve blouse, shorts, and boots.
  • White silk crew neck t-shirt with black shorts and calf-length Chelsea boots

A cropped top and shorts co-ord set with Chelsea boots

How to Pick the Best Chelsea Boots?

How to Pick the Best Chelsea Boots

Chelsea boots are timeless and versatile. You can rock them on any occasion, be it formal, casual, or anything in between. However, it’s important to choose the perfect pair to enhance your overall outfit. Here are some useful buying tips.

  • Material: Chelsea boots are made out of different materials. If you want a more professional look, opt for those made out of leather, while suede boots will give you a more stylish look.
  • Color: Many people buy boots in black or brown colors because they tend to go well with a range of outfits. But if you are in the mood to experiment, opt for boots in vibrant colors.
  • Fit: If you have small or narrower feet, it’s best to pick Chelsea boots with a closer fit around the ankle. Those with wide feet should find styles with more generous spacing and fit.
  • Design: Chelsea boots can have a thin sole to look sleek, while those with a thicker sole are more comfortable. You must pay attention to the boot’s style details to add more oomph to your outfit.

Read Also: Best Women’s Shoes for Standing on Concrete for Long Hours

Summing Up

We hope this blog gave you much insight into wearing Chelsea boots. Undoubtedly, you must be eager to start experimenting with different outfits. If you don’t own the boots yet, use the tips mentioned above to make an informed decision. The right pair of Chelsea boots will help you rock any outfit regardless of the occasion.

About Author
Tommy Nguyen

Tommy Nguyen is a fashion, food, leadership, and business writer who was born in Vietnam and grew up in the United States. Tommy has a degree in Fashion Design. He decided to pursue his interest of writing after working as a fashion designer for many years. Tommy offers practical guidance about how to dress for every occasion. We believe he's definitely worth following!

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