How To Style High Heel Chelsea Boots For Men

High heel Chelsea boots have become a staple in the casual wardrobe of discerning men. Whether you are going for a winter getaway or a relaxed dinner, these boots offer the ultimate combination of style and versatility. With their rich history dating back to the British monarchy, it’s no wonder they’re so popular today.

Originally designed as riding boots, Chelsea boots gained popularity when the Beatles embraced them. Then, it became a symbol of the British mod movement in the 1960s. Since then, the appeal has expanded with various materials and price options.

In this article, we will explore how to wear Chelsea boots for men and choose the perfect pair for different occasions.

How to Wear Heeled Chelsea Boots for Men with Jeans

Chelsea boots and jeans create a classic and laid-back look. Opt for dark brown or black boots to elevate your indigo jeans and casual shirt. It’s important to choose slim-cut jeans that allow the top section of the boot to fit comfortably underneath without being squashed.

Moreover, you can pair it with a white chambray button-down shirt and a matching belt for an easy yet elegant outfit. If you prefer a more polished street style, suede Chelsea boots can add sophistication to distressed denim. Pair them with a fitted plain khaki T-shirt and a black bomber jacket.

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How to Style Men’s Chelsea Boots with a Suit

Chelsea boots can transition from the office to the bar if chosen wisely. When wearing boots with a suit, keep two key points in mind.

First, bring your boots when hemming your trousers since Chelsea boots sit higher on your foot. Then, the hem is shorter to avoid excessive breaks at the front.

Second, choose Chelsea boots with a structured upper that complements suiting and prevents you from looking too casual. Brands like Chamaripa offer suitable options that are worth the investment.

How to Wear High Heel Chelsea Boots with Chinos

For a more dressed-up look than jeans but less formal than a suit, chinos paired with high heel Chelsea boots exude sophistication. Avoid chinos that grip your calves, as they create an unflattering appearance. Instead, opt for slim-cut chinos that comfortably fit over the boot’s upper.

Beige, navy, and khaki colors are versatile options for your casual wardrobe. Pair them with casual shirts in bold colors, checks, or stripes for added interest. During colder months, people will layer with a half-zip jumper or a quilted jacket.

How to Style Heeled Chelsea Boots with a Winter Coat

Heeled Chelsea boots are ideal for winter as they provide warmth and protect against wet weather. When wearing them with a winter coat, opt for a structured wool coat in navy or camel if you’re wearing a collared shirt. Mid-thigh, single-breasted styles or pea coats work well, especially for those on the shorter side.

For a more casual look with jeans and a tee, you can layer a light-wash denim jacket or gilet over a chunky knit sweater for a rustic and comfortable style.

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How to Look After & Store Chelsea Boots

After purchasing a pair of mens high heel Chelsea boots, you should take care of them for the the potential cost of this deal.

Leather Chelsea boots require hydration to prevent cracking, so use a hydrating cream a few times a year to keep them supple and maintain a good sheen.

If you have suede boots, a shoe brush will help keep them looking fresh and remove stubborn stains.

Lastly, consider resoling your leather-soled Chelsea boots by applying a thin piece of rubber called a Topy sole, which extends their lifespan significantly.


Are Chelsea boots still in style in 2023?

Yes, Chelsea boots are still in style in 2023. They have become a timeless footwear option that continues to be popular among men due to their versatility and classic design.

Can men wear Chelsea boots?

Absolutely! Chelsea boots are designed for both men and women. Men can confidently wear Chelsea boots as a fashionable choice for various occasions.

How to style black high heel Chelsea boots for men?

Black Chelsea boots offer a sleek and sophisticated look for men. Here are some styling suggestions:

  1. Pair them with slim-cut black jeans and a crisp white button-down shirt for a modern monochromatic outfit.
  2. Wear them with a tailored suit and a matching black belt for a polished and refined appearance.
  3. Combine them with dark wash denim jeans and a leather jacket for a stylish casual ensemble.

How to wear brown high heel Chelsea boots for men?

Brown Chelsea boots provide a versatile and slightly more casual option. Here are some ideas:

  1. Pair them with dark wash denim jeans and a plaid flannel shirt for a relaxed yet put-together look.
  2. Wear them with chinos and a blazer for a smart casual outfit for dinner or night out.
  3. Combine them with a navy suit for stylish and contemporary business attire.

What socks to wear with Chelsea boots for men?

You can wear no-show or ankle socks when wearing Chelsea boots to maintain a clean and streamlined look. No-show socks are ideal for a sockless appearance. It can provide comfort and prevent the feet from rubbing against the boots. If you prefer wearing socks, choose ankle socks in neutral colors to match your pants.

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2023-09-12 11:09:54

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