Best Chealsea Boots With Suit 2020

One of the most timeless and widely adopted shoe design – Chelsea boots were a popping a part of British attire, used for everything from walking to riding, until the start of WWI. They lost their significance in the fashion industry for several decades and didn’t revive back until the 1960’s popularized by the style icons of the Rolling Stone and the Beatles. Soon they became a symbol of class and sophistication and till date, are loved by both common man and celebrity superstars such as Kanye West.


A solid pair of Chelsea boots will make a good investment as they’re highly comfortable and durable being an iconic addition to your wardrobe as well. Here are our top 10 picks for the best Chelsea boots that have stayed in style for several years and are still considered remarkable by men of all ages.

10 Best Chelsea Boots

1. Blundstone Unisex Original 500 Series

Price: $141.00

The Australian “Blunnies” hold a great reputation for their great comfort and classy craftsmanship. This shoe features the style of a casual boot that offers durability and maximum ease on your feet. All the shoes in the BL500 original series come with an advanced shock protection system consisting of heel pads designed with the XRD technology that reduces the impact on your soles making them last longer and your feet to protect them again blisters and friction. The elastic side panels make it very easy to take the boots on and off. The insole of the show is made of anti-slippery soft leather and the polyurethane outsole offers protection from dust and rind.

For a detailed review about the various Blundstone models, check out our article Blundstone Boots Various Models Review: Original 500 vs Super 550.

2. Red Wing Heritage Men's Chelsea Pull On

Price: $336.00

The Red Wing Heritage line of boots needs no introduction when it comes to a good, long-lasting pair of Chelsea boots. The Red Wing Chelsea boot will go through any situation, any crazy adventure, any work activity and would still look on point due to its strong built and rugged outlook. A rough-and-tough leather upper with a conventional round plain toe will add a vintage look to your contemporary style while ensuring maximum durability. The signature

Red Wing pull tab and elastic inserts provide easy on/off wear and a secure fit to the ankle. The soft leather inner and the sturdy leather and rubber outsole keeps foot comfortable on the inside and offers secure traction on the outside. Red Wing Chelsea boots are a perfect match for you if ruggedness and durability is what you like in your shoes.

If you love Red Wing boots, we have an article for Red Wing boots recommendation. Please check out 6 Best Red Wing Boots.

3. Bruno Marc Men's Bergen Leather Lined Oxfords

Price: $38.99

If you want the sophistication of a Chelsea boot but with affordability, then the Bruno Marc Bergen premium faux leather version is the best choice. This shoe comes in a variety of styles and colors including the casual slip on and the lace up style in black, brown and dark brown. The detailing on the wingtip gives the boots a vintage outlook. Apart from the classy looks, the inner sole is manufactured with cushioned latex for great comfort and a snug fit. The high-quality rubber sole keeps sweat at bay and won’t crack or dry out for a long time. This shoe is a stylish and comfortable piece that’ll add life to your every attire.

4. Thursday Boot Company Duke Chelsea Boots

Price: $199.00

Thursday Boot Company is pretty famous among the Chelsea boot market and is known to manufacture the best suede Chelsea boots for men. First things first – the most attractive and distinctive quality of these boots is the suede upper which pairs these shoes well with every dress attire, whether casual or formal. The elastic on the outsole is not like some Chelsea boots that tends to loosen up with time but offers a close-fitting grip that locks your ankle in place. The Goodyear welt construction offers added support and strength. Some other distinguishing features include water-resistance for keeping the leather dry, insoles made with the comfort of EVA cushioning and an elastic and WeatherSafe treated suede that provides enough room for your feet while protecting the shoes from outer damager.

5. Dr. Martens 2976 Chelsea Boots

Price: $161.99

Before getting into the features of the shoe a little background on the iconic history of Dr. Martens boots. After injuring his foot during a ski adventure in the Alps, Dr. Klaus Marten knew he needed to design a shoe made with an air-cushioned sole coming from powerful rubber tires and this is how the brand stared producing rugged Chelsea boots for all the adventuring loving freaks out there. We’re here talking about the particular 2976 Chelsea boot that comes with a comfortable yet rugged outsole that can even withstand the toughest of works. The SoftWair insole technology features memory foam cushioning for protection against injuries and the synthetic leather upper adds elegance to any casual attire.

6. COMMON PROJECTS Women's 37782015 Pink Suede Ankle Boots

Price: $590.00

Common Projects is relatively a new brand as compared to some old names in the games, but they’ve built up a dedicated reputation in short time. They’re known for designing high-quality footwear made with Italian suede and canvas. Designed with comfortable tapered toes that come in 6 amazing colors, these shoes are highly regarded among middle-aged men. The inner leather sole and the outer thick rubber crepe sole provide comfort and an easy step even on harder terrains. The signature gold serial numbers embossed in gold on the side add a chic outlook to the shoes.

7. FRYE 80009 Men's Greyson Chelsea Boot

Price: $287.00

Made with premium Italian leather and hand-crafted by skilled Tuscan artisans, Greyson Chelsea boots can be your next luxury boot complementing your every attire. The ultra-soft and stunning deerskin leather is hand-crafted from the start – from lining the leather into the shape of the boot to finishing it with aniline dyes. The high traction thick rubber sole gives somewhat a “soldier” outlook while delivering high level of comfort and maximum efficiency at the same time.

The side elastic inserts hold your ankle in place even during long hours while being on your feet. The inner leather sole is of high-quality that gets molded once the boots break in and improves the level of comfort. If you’re looking for a fine-looking Chelsea boot with a little tough outlook, then these boots might be the perfect fit for you.

8. Kenneth Cole Reaction Chelsea Boots

Price: $74.99

A shoe review without the renowned Kenneth Cole getting a mention is incomplete. The company has been selling quality shoes since the 1980’s and continue to provide great looking and comfortable shoes to people till date. This includes the Kenneth Cole Reaction Chelsea boots as well with their elegant outlook and functionality. These boots can be worn during the day while going to an office meeting or at the night when about to go on a dinner date. The seamless stitching and solid built makes them a perfect choice for those looking for quality and stylishness. Apart for their appealing looks, the elastic inserts at the side and memory foam insole makes you feel like walking bare feet on a soft air mattress.

9. ALDO Men's Delano Chelsea Boot

Price: $155.00

Aldo may not be famous enough when it comes to recognized boot appellations, but their stylish designs and reasonable prices have got them a place in our list. One of the best and most appealing designs from their Chelsea boots range is the Delano Chelsea boot. These lightweight and super comfortable leather boots feature a sleek design and classic look. The high breathability makes them a great choice for every season. The shiny leather with a rounded toe design, elastic slip on and a back look – this shoe has the ability to stand out in the crowd.

10. Ted Baker Camroon 4 Chelsea Boots

Price: $250

Ted Baker Chelsea boots can be easily considered the “boots for gentlemen” due to their lustrous and modern outlook. These boots are available either in leather or suede and are stylish as well as wearable and durable. The signature imprinted elastic side panels of the boots are not just for practicality but leaving a style statement too. They also feature a robust rubber heel with a subtle textured panel that distinguishes these boots with other traditional Chelsea boots available on the market. If you’re looking for overall comfort, performance and elegance in a boot, then Ted Baker’s sense of style and passion won’t disappoint you.


With this, our review for best Chelsea boots comes to an end. But if you’re more of a tough guy who needs a tough pair of shoes, then you should definitely check our articles Best Vintage Boot - Red Wing Beckman vs Iron Ranger and Best Red Wing Boots for expanding your options when investing in a good shoe.

Reviewer: Agelina Smith

Best Chealsea Boots With Suit 2020

Review Date: