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How to Wear Men Chelsea Boots

January 02, 2023

The Chelsea boots are one of the best dress boots for men. They have won the heart of many due to it’s sleek and versatile design with elasticated elastic panel for an easy on and off wear. Arguably they are the perfect leather boots for any occasions.

Today we are going to get into exactly how you may want to wear your pair of mens Chelsea boots and go through some of the extremely varied ways they can be worn. If you’re interested in what a Chelsea boot is, its history and how they are made, I would recommend reading our previous article – Chelsea Boots – Beautiful History & Craft  which covers these topics. It will also serve as a guide to the terms and types of information we will be discussing today and this article is written with that knowledge in mind. Once you’ve read that its time to get into the styling of them!


Elastic Sided Boots in Burgundy | Sparrods & Co

Sparrods & Co - Elastic Sided Boots in Burgundy

Chelsea Boots are extremely popular mens leather boots for smart casual outfits. With their laceless design they’re easy to mistake for an oxford wholecut which Is consider the most formal of all oxfords, so its very easy to pair them with a slim or tailored fit suit.

Brown Oxford Wholecut Shoes | Sparrods & Co

Sparrods & Co Oxford Wholecut Shoes in Espresso 

If your office is more of a Chino and polo office, then you’re in luck as a nice Chelsea boot pairs perfectly with both of these things too and gives you plenty of combination options. Chelsea boots are the industry standard choice across most corporate roles. I have friends that are Management Consultants, Engineers, Lawyers and Commercial Pilots that all say its their choice.

With their history as a Paddock boot, it’s also easy to see why they’re popular with tradespeople and farmers. There are options out there for very specialized Chelsea boots with things like Steel Cap toes and reinforced panels and soles for these trade related roles. They’re loved because they’re very comfortable to stand in all day and are easy to take on and off. Some even features straps to make them compliant for different job site requirements.

Today we’re going to talk about three key categories that suit most people for most occasions being; Casual, semi formal and formal. In each category we will discuss what key elements to consider and look for and then how they can be combined and styled.


Key Elements

  • Last: Rounded
  • Leather Types: Informal (e.g. Suede/ Textured Leather)
  • Leather Colors: All of them (Brown, Chestnut, Burgundy, Tans, Other – NOT Black)
  • Sole Type: All of them (Leather, Studded Rubber, Lugged Rubber, Other)

To me, a casual outfit simply anything that doesn’t feature a collar. As society becomes more and more casual the exact definition of casual is getting more and more challenging to define.

In today’s context this could be wearing a pair of jeans or chinos combined with a simple t-shirt. A crew neck jumper could be added for a cooler day and any kind of jacket or coat can be added too if its really cold. The key is having no collar to distinguish itself from semi formal. So what kind of boot would suit this Casual style? Does mens brogue boots and brogue shoes fit into this category? We will explore brogues in the next article.

Sparrods & Co Simba Oxford Brogue Shoes in Burgundy 


Brogue Boots in Black | Sparrods & Co

Sparrods & Co Outback Brogue Boots in Black Calf

Starting with the last, which I’ve suggested a rounded last. This is because a last that has an almond or squared off toe may look too sleek and “European” which doesn’t lead itself well to a casual boot. A boot with a sleeker last may still be worn casually, but definitely limits their variability. This rounded last may look a little more work-wear inspired if its has a bit of extra volume in the toe, but it could also still look fairly sleek overall if you find the right boot with the right balance. The leather choice here is super board because there aren’t really any rules or guidelines for mens smart casual shoes.

My choice would be a mens suede chelsea boots in dark brown because I think it’s the most versatile and interesting color for my wardrobe, whilst also being extremely resilient for rainy days and bad weather.

Suede Chelsea Boots | Sparrods & Co

Sparrods & Co Safari Suede Chelsea Boots in Espresso

A close second would be the standard brown chelsea boots, though I think that a cognac or burgundy shade (a more red or purple hue) are far more interesting and surprisingly versatile as a color. You could also look at a boot with a textured leather like scotch grain or London grain, which further add to the casual look and interest of the overall boots.


Mens Chelsea Boots Australia | Sparrods & Co

Sparrods & Co Safari Chelsea Boots in Burgundy

Much like the leather, the sole choice can be whatever you desire. If you want something that’s going to be more versatile up the formality scale, then I would suggest sticking to a leather or studded rubber sole as they provide the greatest range of use case. If you want to wear these hiking and then to dinner afterwards, then a studded rubber sole might be the better option for you.

Studded Rubber Sole | Sparrods & Co

Sparrods & Co Studded Rubber Sole


Key elements

  • Last: Rounded, Squared, Almond
  • Leather Types: Suede/ Smooth Leather
  • Leather Colors: Dark shades (Black, Brown, Cognac, Burgundy)
  • Sole Type: Leather, Studded Rubber

Semi formal outfits are probably even more broad than casual outfits, but in my definition its anything that has a collar but isn’t a full matching suit. So this could be a rugby shirt, an OCBD or a business shirt with a sports coat, but the pants would have to be a different color to the blazer. This is probably how I personally dress most of the time as it allows me to be extremely comfortable but also suitable for just about any occasion.

Elastic Sided Boot in Tan | Sparrods & Co

Sparrods & Co Safari Men Chelsea Boots in Tan

For a top like I said earlier I would add anything with a collar so a rugby shirt, OCBD or business shirt are all appropriate depending on what you decide to pair them with. With the Rugby I’d suggest a pair of beige chinos or light washed jeans. The same for the OCBD but it can be dressed up with a pair of flannels if you wanted to or it was a colder day. The business shirt should be paired with flannels or woolen suit trousers and maybe the chinos, but not jeans. As for jackets and coats, a workwear jacket or sports coat is appropriate across all options.

As for the Chelsea’s you’re looking for something sleek but simple, understated. You can choose any last style as they can all be found with appropriate shapes for this style. My personal pick would be something rounded or almond as I feel they’re more versatile than a squared toe. 

Brown Chelsea Boots | Sparrods & Co

Sparrods & Co Safari Brown Chelsea Boots

The leather here can be any color but should be of either suede or calfskin leather. Both leather types can be easily worn with a pair of chinos or jeans but also look fantastic with flannels or woolen trousers. I would stick to the darker shades and away from tan colors as they’re harder to match with the rest of your outfit. I’d still stay away from black as it’s a bit less versatile than brown and still looks and feels a bit out of place in this category.

Sole type here is between a leather or studded rubber sole as these are the only two that are really office appropriate for most workplaces. Unless of course you’re an engineer or something and go to job sites frequently in which case a pair of studded rubber soled Chelsea boots combined with chinos and an OCBD is a great look. That’s the thing about Chelsea boots, they’re extremely versatile.


 Key elements

  • Last: Squared, Almond
  • Leather Types: Smooth Leather
  • Leather Colors: Dark(er) shades (Black, Brown)
  • Sole Type: Leather, Studded Rubber

There seems to be fewer and fewer occasions to use a formal boot these days, but when the need arises a Chelsea boot is going to be a perfect choice for you. Visually a pair of black chelsea boots look like a pair of oxford wholecut which is known to be one of the most formal shoes a man can own.

A formal outfit is an outfit where you would wear a full matching suit and probably a tie. This could be a daily uniform if you’re in banking or law, but for most of us it’s an irregular occasion like a wedding or event that we may be wearing a full suit.

Black Chelsea Boots Mens | Sparrods & Co

Sparrods & Co Safari Men Chelsea Boots in Black Calf

Black Mens Dress Shoes | Sparrods & Co

Sparrods & Co Black Oxford Wholecut 

There’s a little less to explain in terms of what to wear in this section, as its basically a full suit. This could be a dark navy blue, a light grey or a dark charcoal flannel and a pair of Chelsea boots are going to look fantastic. The last shape here is anything sleek and European looking, you can choose an almond shape or a more squared off shape if you wanted to, though I think an almond shape is a bit more formal and aesthetically pleasing.

Sadly for most instances suede is out of this round, though I personally think I could get away with it, for most men its better to go for a smooth box calf leather. Either the black or brown will be fantastic here, in terms of raw versatility I think the brown has the edge but if you’re someone with multiple pairs of mens dress boots, or you’re someone who wants a leather boots for men that is specifically designated to be worn with a suit then black leather chelsea boots or black lace up boots would be my choice.

Mens Black Leather Boots | Sparrods & Co

Sparrods & Co Sahara Black Lace up Boots


Mens Black Boots | Sparrods & Co

Sparrods & Co Black Boots for Men 

Either the leather or studded rubber sole are appropriate here, though personally I like the look and the feel of leather under my foot better than studded rubber so that’s my choice. It does make the boot slightly less versatile and useful, and some people are worried about wearing their leather soles in the wet.

Leather Sole | Sparrods & Co

Sparrods & Co Handpainted Leather Sole

In my experience as long as its not your first 5 – 10 wears then a leather sole is fine in the rain, but it does need time to compact a bit under foot first. If you live in a particularly rainy climate than I’d go the studded sole every time

Jessup Says

The Chelsea boot is clearly the master of all occasions, from the most formal to the most casual, there’s a Chelsea boot that will fit your need. They’re a must have for all men and genuinely allow for so much versatility in their style that you’ll probably end up wearing them every day.

If you are considering purchasing a pair of Chelsea boots then I would suggest you consider how you’re intending to wear them most of the time, and then deciding based on the key element criteria we outlined today. Whatever your decision I know they’re going to be a fantastic pair of boots and get many days of wear and love.

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