What Kind Of Pants Goes With Chelsea Boots

Best Men's Pants to Wear With Chelsea Boot

If you are planning to purchase a new pair of pants, you have a wide variety of stylish and classic options to choose from. From casual frayed jeans to professional work pants, there is a style out there suitable for any taste. However, not all pant styles are suitable for your favorite Chelsea boot cut. So, what kind of pants go with Chelsea boots?

Chelsea boots pair best with dark wash jeans, dress pants, and chinos. All three styles evoke a strong sense of style and sophistication. They are also easy to match and tailor toward any occasion or taste. Plus, there is no shortage of these pant styles available in stores.

 If you know where to look, you can easily find a perfect pair of inexpensive, yet sharp, pants to wear with your Chelsea boots. Whether you need to pull together an interview outfit or you want to wear something a little formal to a dinner date, there are numerous options out there to choose from.

 In order to find the best pants for your unique style of Chelsea boots, you will want to explore all three styles we are covering in this article. Let’s take a look at how well dark wash jeans, dress pants, and chinos go with Chelsea boots, respectively

Whenever you make a purchase through links on this page we make a small commission from our affiliate partners. Learn more

Overview and History of Chelsea Boots

GIFENNSE Mens Chelsea Boots Leather Dress Boots for Men 10US Brown

Chelsea boots are defined by their low rise and close fit. Many Chelsea boots also have a tab or loop on the back. These popular boots date all the way back to the Victorian era in the mid-1800s. They were first designed for Queen Victoria, who wanted a new pair of riding boots without laces that would get stuck in her stirrups.

Because they were typically used for horseback riding, most people referred to them as Paddock books. It wasn’t until the boots debuted in the UK and grew in popularity when they were named “Chelsea boots.” Everyone from the Rolling Stones to the Beatles began to wear this boot style.

To this day, the Chelsea boot continues to enjoy a reputation as a highly-regarded staple in fashion. From board meetings to formal events, you can find numerous men sporting this popular shoe style.

Dark Jeans, Dress Pants, and Chinos: Which Option is Best for You?

Chelsea boots have grown in popularity over the years as a must-have wardrobe item for almost any occasion. Whether you are planning a weekend trip to the countryside or a casual dinner with a friend, Chelsea boots are the perfect accessory for any outfit.

Wearing Dark Wash Jeans

Wrangler Men's 20X Slim Fit Straight Leg Jean, McAllen, 36X34

If you are aiming for a classy, yet casual look, go for a pair of dark wash jeans. They are versatile and easy to match with any color boot. While many men elect to wear a pair of black wash or navy jeans, you can also go for a dark brown or navy color. Dark maroon jeans also go well with Chelsea boots.

Whether you are heading out to the bar or the coffee shop for a casual date, dark jeans are a top option.

Best Jean Styles to Wear: Buying Guide

When picking out a pair of jeans, you need to keep the unique cut and style in mind. Some jean types are more flattering with Chelsea boots than others. In general, there are five different jean styles available for men:

  • Skinny — The skinny fit has a tighter fit and is usually low to mid-rise. Most skinny jeans have a tapered leg opening and a zipper fly.
  • Slim — Slim jeans should fit snugly, but not too loose or too tight. They usually have a mid-rise and narrow leg opening.
  • Regular — Generally mid-rise, these jeans fit looser than skinny and slim jeans and have a large leg opening.
  • Relaxed — Unlike skinny or slim jeans, relaxed jeans do not hug any part of the legs. They have a fit that is a little looser than regular jeans. They are usually mid-rise.
  • Loose — Loose jeans fit that baggiest on people. They provide much more room in the legs and buttocks area than the other types of jeans.

You should also consider the rise of the jean, which refers to the distance between the crotch and the top of the waistband. High rise jeans tend to rise above the belly button area. On the other end of the spectrum are low rise jeans, which sit below the belly button and around the hips.

Wearing the Right Type of Dress Pants with Chelsea Boots

dress pants to go with chelsea boots

Photo by cottonbro

For business meetings or luncheons, wear a pair of dress pants with your Chelsea boots. Add a blazer and shirt to complete the look. Dress pants come in a variety of colors, including black, white, tan, red, and even yellow. Depending on how formal, or informal, the event is you can feel free to experiment with the colors of your pants and shirt.

Dress Pants Buying Guide

Men’s dress pants come in a variety of styles, including:

  • Flat Front: Dress pants with a flat front have a streamlined design. Flat fronts tend to look best on men with a lean build.
  • Pleated: Pants with a pleated fit offer more room in the waist and leg area than flat front styles. Pleated plants often balance out men with broader shoulders.
  • Wide Leg: Wide legs are also suitable for men who have a larger build. They can balance out a broader upper body thanks to their loose-fitting style.
  • Cuffed: Cuffs add an elegant touch to many pant styles. Often times, they will accentuate your height and style.

Picking a pant style that is both flattering for your body type and comfortable is important. As you try on different pairs of dress pants, make sure you pick a fit that fits properly around the seat and thigh without being too baggy. The rise of the pants should also fit naturally with the shape of your body.

Wearing Chinos this Chelsea Boots

Volcom Men's Frickin Slim Chino Pant, Black, 32

In general, chinos are considered to be less formal than dress pants. Like this Volcom Men’s Frickin Slim chino pant. Nonetheless, chinos are also perfect for semi-formal events. Many men wear a dress shirt or sweater with their chinos and Chelsea boots. To achieve a more formal look, finish your outfit off with a matching suit jacket.

Chinos Buying Guide

The right size Chinos will fit over the legs without being too tight. They should streamline your look and create an elongated effect for the overall outfit. Chinos should never have a long hem. Instead, they should fall just around the ankle.

Chinos come in a number of different colors, including maroon, light blue, violet, and red. Classic couples like khaki and navy are also popular choices among men. If you are attending a more formal event, a classic color would be more suitable. However, you can experiment for more laidback or lively events.

Pants You Should Avoid Pairing Your Chelsea Boots With

While Chelsea boots complement a variety of pant styles, they also tend to clash with some other styles that are considered to be on the more casual side. You should avoid wearing your Chelsea boots with these types of pants:


Sweatpants are fine to pair with sandals and sneakers, but not Chelsea boots. They are too loose-fitting and casual to properly match the style of Chelsea boots.

Harem Pants

Harem bands are known to be a comfortable pant style. They are popular for fitness activities such as yoga or warming up for a workout session. Many men also wear them just for relaxing. However, they do not match well with Chelsea boots.

Cargo Pants

Known for their casual, military-style, cargo pants go great with sneakers. But because of their laidback style, they tend to look mismatched when worn with Chelsea boots.

Sailor Pants

Sailor pants typically have a wider leg opening than the previously mentioned styles. Many times, when you pair your Chelsea boots with a wide leg pant, the pant overshadows the boot. As a result, you should avoid pairing these two pieces together.

Many of these styles simply don’t go well with the cut of the Chelsea boot or are too casual to match with them.

Men’s Pants That Are Challenging to Style with Chelsea Boots


Jodhpurs are trousers that are typically worn for horseback riding. Of course, you don’t have to saddle up on a horse if you want to wear your favorite pair of jodhpurs. While many jodhpurs run down to your ankles, some only reach your calves. If you want to pair your jodhpurs with your Chelsea boots, make sure you are wearing full-length jodhpurs.


When styled right, shorts can go well with Chelsea boots. However, most of the time, they end up clashing together. Athletic shorts especially do not match well with the formal style that Chelsea boots are known for. If you want to try to match shorts with Chelsea boots, try out a jean or cargo short style.

When it comes to finding the best pant to match with your Chelsea boots, there is no singular answer. Finding a pant style that pairs well with your boots while also flattering your natural body shape is important. Try out these pant and Chelsea boot combinations the next time you are out and about on the town.


9 Wardrobe Must Have to Wear with a Crew Neck Sweater

5 Pants to Wear this Winter If You Are Sick Of Jeans

How Often Should You Wash Business Shirts and Work Clothes?

9 Thing to Consider When Choosing the Right Fit Sweater

What are the Best Quality Men’s Boots – Wilcox Boots vs Timberland Boots

Men’s Dress Watches – 9 Questions To Ask Before Buying

Recent Posts