Chelsea Boot Buying Guide
Introduction
This guide came about from the recent crowd sourcing discussion on content the community wanted or felt was missing from /r/malefashionadvice. And surprisingly enough no one has yet written a guide on Chelsea boots so I thought I'd give it a go.
How to use this Guide
Consider what budget you have in mind, read the short description of the brands, and browse the Style Example albums listed under each brand for what type of Chelsea boots they sell.
Look at silhouette (sleek to chunky), the types or colours of leathers they use, and the soles (leather or rubber/slim or chunky).
If you like the look of what you've seen look at their websites or stockists which carry them. Do your own research and ask some question on this thread or /r/malefashionadvice's Daily Simple Question threads.
Ultimately use this guide as a springboard.
On prices
This guide contains a lot of different brands at different price point. They are organised by recommended retail pricing (RRP) for ease of putting in a list. Obviously a some of brands. like J.Crew, have business models where everything is always on sale. If that's the case it's mentioned in the brand overview.
Retail prices will be listed below, but you can consult /u/sconleye's Beginner’s Guide to Buying Expensive Clothes for Less on ways to grab a bargain and not pay RRP.
Some brands will have notations for (EU) or (UK) to make it easier for people in those places to buy more locally and not get hit by high shipping, return costs and custom fees.
Where is [x brand]?
I’m sure you’ll notice there are a few brands that aren’t included here. There are a number of reasons – some I couldn't find much info on, I didn't want to include to many options in each tier bracket, or some I didn't know about/didn't find much info on when researching for this guide.
If you can think of a brand you're particularly fond of or own feel free to comment below with any information.
Characteristics of a Chelsea Boot
Ankle height.
Typically Low heels.
Two parts each made from a single piece of leather: the vamp and the quarters.
The vamp and the quarters meet near the ankle where they are joined by a strip of vulcanized rubber or elastic.
The strip of elastic extends to just below the ankle but not all the way down to the sole (just above the welt).
The vamp and quarters are not sewn one on top of the other. Instead, they are sewn together in one plain below the ankle.
A History of the Chelsea Boot
The extract below is mainly from The Gentleman's Gazette:
Designed around 1851 for Queen Victoria by her personal shoemaker the Chelsea boot has been in out and out of fashion ever since.
In 1839, Charles Goodyear, of goodyear welt renown, developed a process to vulcanise rubber in Springfield, Mass., which was patented in 1844. The same year, the British Thomas Hancock claimed to have also invented vulcanisation independently for which he received a British Patent in 1844. What matters though is that without vulcanised rubber, or elastic as we call it now, the Chelsea boot as we known it would not exist.
From the Victorian Age to just before World War 1 the Chelsea boot was initially used by both men and women as walking shoes. During this time they also were used as casual riding or outdoors boots which saw the shape of some boots change to a less chiseled look. Some even claim they were referred to as Paddock boots at one point in time.
In the mid-1950s, a group of creatives consisting of young artists, film directors, and socialists started frequenting the King’s Road area in West London. This group was named the ‘Chelsea Set’ by the media, and they made the name ‘Chelsea’ synonymous with a new way of living and dressing. This group, which included well-known fashion icons Mary Quant and Jean Shrimpton, started favoring the Paddock boots and soon they began to be considered the ultimate leisure accessory and hence were renamed to Chelsea Boots.
London’s theatrical shoemakers, Anello & Davide, re-interpreted the Chelsea boot in the early 1960s by fitting it with a Cuban heel. Their version was known as the ‘Baba boot’ and entered the world of rock & roll. As was expected, their popularity skyrocketed. The main reason for this was the fact that The Beatles were very often seen wearing them. Legend has it that John Lennon and Paul McCartney each bought a pair at Anello’s shop at 96 Charing Cross Road on the way back to Liverpool from Paris in October 1961. In 1962, George Harrison and Ringo Starr joined them and paired with suits so they would look like a uniform. Soon they came to be known as ‘the Beatle boot’.
It was also during this time when the image-conscious Mod subculture started wearing tailored suits, drove customized scooters, and wore Chelsea boots. It is quite difficult to ascertain exactly why Chelsea boots were considered the height of Mod fashion, but it is thought that apart from well-known rock and roll bands ( The Rolling Stones wore them as well), French and Italian cultural influences combined with the popular American greaser look played a significant role. Interestingly, the character Steed from the sixties TV Series Avengers would always wear Chelsea boots, not matter whether it was a combination, three piece suit with a bowler hat or a tuxedo.
So there you have it, a 167 year old boot worn by royalty, singers, rockers, creatives and subcultures to boot.
A Quick Footwear Primer
The next couple of paragraphs are from /u/Nipplemonger's Beginner's Guide to Footwear
Good dress shoes and boots are generally more expensive than sneakers and casual shoes, but they will last a long time with proper care. Additionally, a good shoe is built on a leather insole, which will mold to your foot over time, and become extremely comfortable, given that the shoe fits properly. Generally, good quality Chelsea boots will be made using a stitched construction, which includes goodyear welt, blake stitch, blake/rapid.
Construction method: Shoes made with a stitched construction can be resoled, which means that a well cared for pair of shoes can last for many many years. Modern glue is quite good, but using a cemented construction is usually a cost-saving measure, which would also be reflected in the shoe’s leather quality and durability. As a general rule of thumb, stick to goodyear welted, blake, or blake/rapid construction shoes for your dress shoes. Any decent shoemaker should disclose the method used.
Leather: You want full grain leather, as it will age better than corrected grain leathers, which are coated with plastic that will crack over time. Generally, smooth leathers are more formal than suedes. Fine-grained calf would be most formal, while suede, grained leathers, and shell cordovan would fall somewhere below that.
Color: Once again, very broad strokes here. Black is pretty formal, lighter shades of brown are more casual, and generally darker browns are pretty versatile.
Soles: A leather sole is slimmer and more formal than rubber soles. Lugged, vibram or crepe soles are even more casual. If you opt for a leather sole you can always get a thin sole protector added by a cobbler, colloquially known as a 'toppy'.
TL;DR version
Below $100
ASOS
H&M
AliExpress / Taobao/ Alibaba clones
River Island (UK + EU)
New Republic
$100-200
Will Vegan Shoes
Marks & Spencer (UK)
Dr. Martens
Frye (US)
Shoe the Bear (EU)
Bexley (EU)
Meermin (EU)
Blundstone
$200-400
Jack Erwin
Loake 1880 (UK)
Wolverine
J.Crew
Taft Clothing
Red Wing
Story et Fall
Scarasso (EU + UK)
Rider Boot Co.
Shoepassion (EU)
$400-700
Common Projects
Tricker's
From the First
RM Williams
Carmina
Alfred Sargent
Enzo Bonafe
Crockett & Jones
$700+
Viberg
MM
SLP
$100 and under
Around the $100 budget and other you're getting cheap boots where the upper is cemented/glued to the sole. Leather quality can vary from OK to bad. Opt for suede over calf leather since cheap suede looks better, whereas cheap calf can get some nasty creases.
There's nothing wrong with buying boots at this price if you just want to try out the style before dropping money on something better. Or if you have a large enough rotation that cheaper stuff doesn't matter.
However if you can stretch your budget higher, do it.
ASOS - $45-90 RRP
British based fast fashion retailer. Massive webstore with a lot of own-brand and branded items. Free shipping to the US, Canada, UK, Europe and most countries. Free returns for the US, UK and other random countries. Go for the suede since cheap suede tends to look better than cheap calf leather. Reviews tend to say sizing is true to size (TTS) or half a size below. ASOS offer a student discount also which puts down the price by 10%. Offers normal and wide fit.
Purchasing: ASOS website
H&M - $60-70 RRP
Swedish fast fashion retailer. Second largest global retailer in the world. Has a variety of stores in most major cities or large towns. Suede and calf on offer, opt for suede. Sizing ranges from true to size to going down one full size according to online reviews. Best to try in-store if you can.
Purchasing: H&M website
AliExpress / Taobao/ Alibaba clones - $75-80 RRP
Your favorite Chinese webstore which caters internationally. You can find a lot of replicas online, especially ones which look like Common Project Chelseas. Moral debates about replica clothing aside, people have been buying these on reddit for the last couple of years. Sizing is based on foot length so use their sizing chart and pay attention.
Purchasing: AliExpress
River Island (UK + EU) - $80-100 RRP
British fast fashion clothing brand. Sizing is true to size. If you're based in the UK I would consider these if you can try them on in-store. Suede over calf leather as outlined above. Apart from that nothing really stands out.
Purchasing: River Island website, ASOS
New Republic - $99 RRP
New Republic by Mark McNairy is a relative newcomer to the block. It is a diffusion line of the designer Mark McNairy. Suede offerings only. The footwear is not stitched unlike his mainline. For sizing you should go down by half or one full size down. One comment recommended doing with your Clark's Desert Boot (CDB) sizing.
Purchasing: New Republuc website
$100 to $200
Traditionally used to be a no man's land for quality footwear. Now you have a few more options which either use stitched construction or to fill a certain consumer niche. Leather quality is better than the tier below so you can consider calf.
Will Vegan Shoes - $110 RRP
If you're a vegan then Will's Vegan Shoes could be just for you. They offer faux suede leather which is made out of water-resistant and breathable microfiber. They also offer free shipping and returns for US, UK and select European countries. Has a mix of faux suede and calf leather and options of thin rubber to thick lugged soles.
Purchasing: Will Vegan Shoes website
Marks & Spencer (UK) - $120-$135 RRP
Well known British highstreet brand. Used to be known as that place your grandparents used to shop but in the past couple of years they've been putting out some decent stuff. Boots are true to size and the suede is decent quality for the price.
Purchasing: Marks & Spencer website
Dr. Martens - $145 RRP
A British brand known for it's cultural impact, often worn by many different subcultures throughout the 1970s to now. Well known for a horrendously long break in period. After which they become very comfy due to the air-cushion insole. If you go workwear, goth, punk, rock or whatever then these might be the ones for you. Though technically welted they used a heat sealing which make them difficult to resole. Often local cobblers won't touch them, so you have to send them off to be resoled to Doc Marten themselves.
Purchasing: Dr Martens website
Frye (US) - $150+ RRP
Reputably the oldest American boot making company in existence. Offers a mix of chunkier workwear styled boots and typical plain slim Chelsea boots. Has a lot of different lines at a lot of different price points. Leather can be pretty poor quality compared to others in the price tier of each specific model. However if you like them and get them on discount, which they are on a lot, it's not too bad a purchase. Stocked on by Nordstrom, Amazon and other large retailers.
Purchasing: Fyre website, Nordstrom Rack, Amazon
Shoe the Bear (EU) - $160 RRP
Scandinavian shoe brand which has been around since 2007. Offers a large selection of Chelsea boots in different colours, styles and shaft heights. Leather outsoles. Can be found on their own website, Zalando, and Urban Outfitters. True to size and comfort of the insole is meant to be good. Blake stitched.
Purchasing: Shoe the Bear website Urban Outfitters
Bexley (EU) - $170 RRP
French manufacturer offering a large range. Offers a small range of Chelsea boots. Bexley offers a double deal (1 pair for 139€ - any 2nd pair from their range for 99€) which may be it's only draw when compared to the similar price brands. The weak Euro compared to the USD make it an attractive option for international buyers. Blake stitched. A good entry level boot into stitched footwear. Sizing is true to size.
Purchasing: Bexley website
Meermin - $175+ RRP
Spanish shoemaker with arguably the best bang for your buck in this price range. Offering suede, calf and museum calf, among others. Chelsea boots on offer include shorter shafts. Sold exclusively through their own website, they have a variety of attractive boot options around the $175 and depending on make-up. Particularly attractive given the weak euro. Interesting GMTO options on website as well which are regularly refreshed. Keep in mind shipping though - they come from Spain, but they arrive with great praise behind them. Recently opened a store in New York so arguably the best time to buy for US customers.
Purchasing: Meermin Website, factory seconds outlet
Blundstone - $185 RRP
An Australian footwear brand, there boots are colloquially known as 'blunnies'. Hard wearing slip on Chelsea boots which you can wear in snow, mud, farm or outback. Obviously a very workwear and utilitarian style. Sizing is roomier under the assumption you're going to be wearing thick socks.
Purchasing: Blundstone website
$200 to $400
This tier is where the going gets good. Quality of material is a jump up. Different brands tend to have different aesthetics so have a browse and find which jives with or your style.
Jack Erwin - $220 RRP
Budget American shoemaker. Range of goodyear welted (Sullivan collection) and blake-stitched (Foster collection) boots in derby and Chelsea styles. Reviews in general are average, in particular focusing on average leather. Expected at this price point. True to size.
Purchasing: Jack Erwin website
Loake 1880 (UK) - $220-260 RRP
British shoemaker’s high quality line and perhaps only one worth considering. 1880 line boots are made in Northampton. Good quality, but below those of other English bootmakers. Can be somewhat hard to fine in North America but that has been changing of late. A lot easier to find in the UK. Sold in their own webstore, department stores and online by quality shoe retailers like Pediwear. Sizing ranges from true to size to down by one, depending on model.
Purchasing: Herring Shoes, Pediwear
Frugal: Official Loake factory outlet, North Shoes' outlet & North Shoe Cambridge outlet
Wolverine - $220 RRP
Purchasing: Wolverine website, Amazon
Oft-recommended American workwear bootmaker. Decent workwear aesthetic with varying quality control. Many examples have been subject to poor creasing. Viable at relatively regular sale prices. Despite some issues, overall a very attractive boot for a certain style.
J.Crew - $250 RRP
/r/MaleFashionAdvice's darling. Offering relatively in-offensive good quality basics at a decent price (read: they're always on sale). There Kenton Chelsea Boot retials for $250 but can often go down to ~$150 on sale. Goodyearwelt construction with a mini-lugged sole. Sizing is true to size.
Purchasing: J.Crew website
Taft Clothing - $250-275 RPP
Taft offers sleek, fashion-forward styles at a reasonable price point. They began producing Blake-stitched shoes and boots in Spain and recently added a line of Goodyear-welted options made in Portugal. Taft is known for offering good construction, solid quality control, and great customer service. Overall, the consensus has been positive on /r/goodyearwelt. Sizing recommendation is to go down either half a size or down one full size.
Purchasing: Taft website
Red Wing - $260 RRP
The standard to which workwear styles are compared. Known for Iron Ranger, Beckman and moc-toe boots but also offers a workwear styled Chelsea boot model called the Rancher. Solid construction and respectable QC. Operates own tannery (SB Foot), which keeps leather quality high at this price point. Originally a European only model but sold in the US now. Only small amount being sold so finding on sale might be harder.
Purchasing: Too many to list really. Numerous department stores and high end clothing shops, as well as own stores. Everywhere from Amazon to unique online retailers.
Frugal options: Sierra Trading Post, Nordstrom Rack for factory seconds.
Story et Fall - $260 RRP
Massive rise in popularity given recent trends in men’s fashion, known for sleek Chelseas and jodhpurs at cheap prices. Models range from goodyear welted, blake-stitched and cemented. Models have varying heel height. Website is pretty poor at the moment, but can contact by email and see options here. Free international delivery a bonus, and have been relatively well reviewed. Customs are paid by the customer.
Purchasing: Story et Fall website
Scarasso (EU + UK) - $265-310 RRP
A European brand which is based in Germany, with footwear made in Italy. Good quality for the price, with the company purportedly running on small profit margins. Attractive lasts and leathers used.
Purchasing: Scarasso website
Rider Boot Company - $280-400 RRP
An American based company with a American twist on European styling. Made in Italy. Arguably some of the most attractive designs, with top drawer quality and pleasing last shapes. Ron Rider makes some highly attractive and well sought-after options. Have also operated successful shell cordovan GMTOs. A variety of prices depending on model, can be found on Massdrop occasionally.
Purchasing: Rider Boot Website
Shoepassion (EU) - $280-340
A German based shoe brand with a cringy worthy name. Goodyear welted with many models offering winter ready sheepskin lining and hardy outsoles. An alternative for Europeans to look at.
Purchasing: Shoepassion wesbite
$400 to $700
At this tier brands start to offer Made to Order (MTO) options on leather used, sole options, and lasts. Each brand tends to have it's on specific style or take on Chelsea boots and boots in general.
Common Projects - $460+ RRP
A well known American-Italian luxury footwear brand for it's minimalist sneakers. They also a suede Chelsea boot with a crepe sole, but have recently branched out and made a few in calf leather. Past wisdom was to size down one size like their Achilles sneaker, but recent models are more true to size. Also branches out recently in making calf Chelseas in brown and black calf.
Purchasing: Mr Porter & END Clothing
Tricker’s - $470+ RRP
Renowned English shoemaker, manufactured in Northamptonshire. Very well constructed, and are known for having reputable QC. Best known for use of chunky natural welts. Wide range of leathers and styles, as well as an extensive MTO/GMTO service. Also offer shell at a higher pricepoint. Can often be found for less on end of season sales.
Purchasing: Tricker’s Website, Pediwear, Leathersoul, Tricker's outlet
From the First - $480 RRP
Wildcard option here. From the First is a relatively new Parisian brand with a presence on Instagram. Offering made in Italy boots in Chelseas, anke zips and harness styles. Delivering Chelsea boots with a SLP style at a cheaper price point.
Purchasing: From the First
RM Williams - $495 RRP
Tough Aussie bootmaker now more prized for attractive and fashionable boots. Best known for their Chelsea boots, which are the only wholecut chelsea at this price point. Also do lace ups, which have been reviewed but are pretty hard to come by. Buying from Australia is much more cost effective from sites like Bbootsonline.au & Nungar.
Purchasing: Website, Boots Online, Nugar, Pediwear
Carmina - $520 RRP
High quality Spanish maker on the dressier end of the spectrum. Incredibly attractive boots with top quality construction. A darling of /r/goodyearwelt having organised exclusive GMTOs through them. Recent price hike makes them slightly less good value, but still one of the best quality/price ratios out there.
Purchasing: Carmina website, Skoaktiebolaget
Alfred Sargent - $540
A classic, high quality English bootmaker. Manufactured out of Northamptonshire, they are a bit hard to come by, since they have no standalone stores in North America. Have collaborated with J. Crew, and worked on behalf of Peal & Co. before.
Purchasing: Herring, A Fine Pair of Shoes, Tredders
Enzo Bonafe - $590 RRP
Italian shoemaker known for high quality MTO shoes and boots in almost any style you can think of. High quality/price ratio given the MTO offers and handwelted construction. Ever-growing in popularity and for good reason. Generally on the dressier side of the scale. Please note shell options can be $800+.
Purchasing: Skoaktiebolaget, Solegarb Shop Mehra MTO
Crockett & Jones - $600+ RRP
Quintessential English bootmaker manufactured in Northamptonshire. Known for high quality and attractive models. Variety of leather options available including shell. Options come in boots of different shaft height, colours and leathers. A range of different options and different price points ranging from $600 to $700+
Purchasing: C&J Stores, Barney's, Pediwear
$700 and above
Disclaimer:
Above the $700 range you have a lot of options and these are just the ones you see a lot on reddit. Not everything in this tier are represented.
Plus if you're spending this much money on a pair of Chelsea boots you really shouldn't be reading a guide written by me, you should be doing your own research.
Viberg - $700 RRP
Probably one of the best known high-end brands on GYW, Viberg make high quality workboots out of Victoria, Canada. Prized for their slim toe boxes, attractive styles and lasts, interesting and varied use of leathers, and unique collaborations. It’s difficult to go wrong with a pair. Expect new releases to sell out fast, and rarely go on sale. Recently started using GYW construction alongside stitchdown options.
Purchasing: Viberg website, Full list of Stockists, Collaborators: (3sixteen, Haven, Gentry, 14oz Berlin, Notre, Superdenim, Kafka, the Bureau Belfast etc.)
Maison Margiela (MM)- $950+ RRP
Maison Margiela (MM), formally Maison Martin Margiela (MMM), is a French luxury brand. Founded by the secretive Martin Margiela who has managed to keep out of limelight, the brand reflects his minimalist approach in its styling. Made in Italy.
Example stypes. Please note that MM make popular ankle zipper boots each season but I haven't included them because they're not technically Chelsea boots.
Saint Laurent Paris (SLP) - $945-$1,045 RRP
Saint Laurent Paris (SLP), previously Yves Saint Laurent (YSL), was revitalised under Hedi Slimane's tenure as creative director. Hedi in his turnaround of the brand introduced a look more based around rock, androgyny and the heroin chic of the 1990s. He left the brand in March 2016. There Chelsea boots are very slim with attracrive silhouettes with heels of ranging heights. A Grail purchase for many.
Further readin, sources and thanks to, etc:
/r/goodyearwelt, /r/streetwear, /r/malefashionadvice
Gentleman's Gazette's Chelsea Boot Guide
Beginners Guide to Footwear by /u/Nipplemonger
[Megathread] Your Favorite ___ For $___: Chelsea Boots by /u/Coveo
/r/goodyearwelt's 2018 Beginners Boot Guide by /u/Rioc45 and many other GYW contributors
Inspiration specific:
Ultimate Chelsea Boot Inspo Album and Ultimate Chelsea Boot Inspo Album V2 by /u/MakeMoneyNotFriends