The Chelsea boot is a staple of any gentleman’s wardrobe. Yet, there exist many different styles of Chelseas to choose from and this diversity can make it difficult to pick the right one for you.
In this guide, we discuss some of the aspects you should consider when selecting your own pair of Chelsea boots. We’ve also listed the best Chelsea Boots found on Zappos as they have a varied inventory that lets you browse across many different brands and price points in the same place:
What To Look For In A Pair Of Chelsea Boots
If you’ve already started to scour the web for a pair of Chelseas, then you probably already realized that “it’s a big world out there.” There are literally millions of different types of Chelsea boots to choose from… where does one even begin?
In our opinion, there are three characteristics to consider when picking out a pair of Chelsea boots. In no particular order, these are:
- Material
- Sole
- Design
Next, we break down these three “pillars” so that you may then build your own mental framework for the Chelsea boot that you want.
The Material
Much like other types of men’s shoes, Chelsea boots come in many different materials – from premium Italian suede to synthetic rubber and everything in between.
As you can guess, the material is going to play a big part in how the boot will look and, ultimately, what other articles of clothing you’ll be able to pair it with. Subsequently, it’ll also determine the formality of your boot and the settings in which it’s appropriate to wear it.
While sometimes you can get away with a casual material in a Chelsea boot pairing well with a more formal outfit given the dressy nature of most Chelsea boots, this should be considered the exception rather than the rule. Therefore, before taking the plunge on a specific pair, think of the occasions in which you’d like to wear Chelsea boots and let that thought drive the material you chose to go for.
Broadly speaking, a Chelsea boot crafter in calfskin leather will be the most formal. Less formal would be something like a suede or nubuck pair of boots, and least formal would be any material that is not leather such as rubber or fabric.
Type Of Sole
Along the same vein as the type of material is the type of sole on the boot. Once again, Chelseas are made with many different types of boots.
For instance, some Chelsea boots have a Goodyear welt or blake stitch construction that gives them a very dressy essence. Others possess bulky rubber soles that make them look a bit more burly and rugged. Some have a bit of a heel and yet while others have none at all.
A worthy mention in the realm of Chelsea boot soles is the crepe sole. While not unique to Chelsea boots, this natural or synthetic rubber sole offers a unique cream-tone look that is quite popular. It’s not as formal as a leather sole (such as those encountered in a Goodyear welted Chelsea) but has become incredibly widespread likely because they allow boots to remain relatively affordable.
The Design
The overall design of a Chelsea boot is the third and final characteristic to consider.
Indeed, the two previous points, the sole and the material, are building blocks within the overall design of the shoe. However, the design also takes into account other details, including whether the Chelsea boot will have other types of decorations such as broguing on the leather, how broad the elastic gussets will be or if they’ll be in a contrasting color, if “pull tabs” will be used, etc…
They’d be too many to list here, but in browsing a couple of dozen listings online you’ll get a sense of the broad design concepts used by different Chelsea bootmakers.
One of the best online repertoires to get a sense of the many varied types of Chelsea boots that exist is Zappos. While many individual shoe manufacturers claim to make the best Chelseas, none of them make their boots in varied enough styles.
With Zappos’ extensive online inventory, you can become familiar with a broad range of boot styles from every part of the formality spectrum. Perhaps most importantly, you can shop all of them with peace of mind knowing that they’ll be delivered promptly and that you’re protected by a generous return policy if the fit isn’t perfect.
Our Favorite Chelseas On Zappos
Below are some of our favorite Chelsea Boot styles we found on Zappos. If you prefer to do your own searching, use this link to go directly to search results that are filtered for Men’s Shoes and “Chelsea Boots.” Otherwise, continue scrolling to read on.
- Style: Chelsea Boot
- Formality: Business Casual
- Pricing: $398 [Buy Now On Zappos]
The Shelby Chelseas from To Boot New York are an exceptional example of what a dressy pair of Chelseas should look like. Beginning with the supple Italian suede upper in brown, the design of the boot is further augmented by its slender profile and measured 5-inch shaft.
Also elevating the pedigree of these boots are an almond toe profile and hybrid leather/rubber outsole that melds the look of a traditional boot style with the comfort required to wear these all day – not that you’d have a difficult time doing so given how alluring they are.
- Formality: Business Professional
- Pricing: $375 [Buy On Zappos]
When compared to the previous To Boot Shelbys, these Magnanni Rileys in black calfskin exemplify how small changes in the material can give a pair of Chelseas a different personality.
In this tone of leather, and considering the premium construction and materials, the Rileys could even fit into a business professional setting, unlike most boots. A leather lining, cushioned footbed, and rubber outsole would also ensure that comfort is not sacrificed.
- Colors: Black, Grey, Tan
- Material: Suede w/ Crepe Sole
- Pricing: $139.99 [Buy Now On Zappos]
The Cedric suede boots from Thomas & Vine are a great example of the crepe sole style of Chelsea boot that we mentioned earlier in this article. They also help demonstrate how the crepe sole is often paired with lighter tones of suede for a killer combo.
Naturally, these Cedric Suede Chelseas also possess matching elastic side gorings, a leather tab at the back, and padded footbeds (Tru Comfort Foam), all at an affordable price point.
- Formality: Winter Boots
- Pricing: $239.95 [Buy On Zappos]
These Blundstone Thermal Chelseas are a prime example of a Chelsea boot that can be worn as a winter boot.
Too often, winter boots are a chore to put on due to their laces. However, normal Chelseas generally don’t provide the insulation necessary to keep your feet warm in the winter.
The Blundstone 584 solves these problems with waterproof leather, Thinsulate linings, a sheepskin footbed, Shock Protection System Xtra that reduces pressure points, and more. These could also work well as work boots but we think that as the leather wears in, they’ll develop an attractive patina that makes them a great pair for those chilly winter nights out with friends.
- Formality: Work Boots
- Pricing: $149.95 [Buy Now On Zappos]
Dr. Martens has a long-standing reputation as work boots but recently, younger crowds have brought them into vogue. This is incredibly convenient as it allows you to wear a sturdy pair of Chelsea boots without looking out of place.
Not just an avant-garde fashion statement, the Dr. Martens 2976 Chelseas also impart comfort with a cushioned footbed but also confidence with a Goodyear-welted construction and air-cushioned outsole renowned for its slip resistance.
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