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You are currently viewing Samuel Windsor Review (2021)

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Samuel Windsor’s reviews are relentless.


Samuel Windsor's trustpilot score.


The British menswear company has a 48% ‘bad’ score on trust pilot? Ouch.


But, I’m glad to say, my experience was somewhere in the middle.


In this Samuel Windsor review, I will cover my experience with their customer service, and my experience buying and wearing some Samuel Windsor shoes (their ‘Prestige Chelsea Boots’, to be exact).


Review of Samuel Windsor’s Customer Service, Delivery & Packaging

I was on the hunt for a pair of Chelsea boots that wouldn’t break the bank, and surfed the web, viewing all available options from every shop under the sun.

But after hours of searching, there was no clear winner.

I then remembered a brand that I had heard of in the past, Samuel Windsor, and after a quick visit to their website, found their ‘Samuel Windsor Prestige Chelsea Boot’.


‘Goodyear Welted’ and ‘Italian Leather’ – for £49.95? Sounds too good to be true.


So, I bit the bullet, and ordered them 10 minutes before the ‘same day dispatch’ pledge.


Samuel Windsor's Prestige Chealsea Boots in black.
A photo of the product from Samuel Windsor’s website.


I kept checking my inbox for a confirmation e-mail.


1 day2 days3 days – 4 days – nothing.


Alarm bells started to ring, and I frantically started googling more reviews of the company.


Although the reviews for Samuel Windsor’s shoes were all mostly positive, the reviews of the actual company were all mostly negative.

I called their customer service to see what had happened to my order, and was put through to a lovely Woman who told me that there was ‘a problem in the warehouse’.


She then said she would ‘upgrade me to one-day delivery’ – a lovely gesture!


Satisfied, I put the phone down and forgot about it.

Two days had passed and still nothing had arrived, so I again called their customer service and was told that there had been an ‘issue with the courier’, this time by a less friendly lady who quite frankly scared the crap out of me.


After getting off of the phone, crossing my fingers and waiting a few more days, I eventually received a parcel.


Tearing into the covering like a kid on Christmas morning revealed a pleasant, ivy green shoe box. I opened it, and there sat my ‘Samuel Windsor Prestige Chelsea Boots’.


Customer Service

Overall, the customer service was average to poor.

Two promises were broken:

  • They didn’t dispatch the package on the day that I ordered it. (Like the promise had suggested)
  • They didn’t dispatch it when I contacted them for the first time.


On top of this, I was getting a very hostile vibe from the second lady that I talked to, reminding me that ‘I have already told you what has happened’ when I asked for further details.

However, the package did get to me eventually, even if it wasn’t as quick as I had hoped.

However, I have ordered from them since with no problems.


Samuel Windsor Returns & Delivery

Delivery was via Hermes.

If you’re not happy with your product, you can:

  • Send it back through Royal Mail at your own cost
  • Buy a pre-paid returns label at the online checkout for £1.50.


Unfortunately, there is no free returns with Samuel Windsor, though the prepaid £1.50 charge is a good solution for both parties.



The box was nothing special, but it did the trick.


Overall, I give Samuel Windsor’s customer service, packaging and delivery that I experienced a 2/5.

There were many problems that arose in this transaction that I have never experienced from another company before, and should’t have happened.

Is saving a bit of money worth your time and hassle exchanging countless messages with customer services?


Samuel Windsor Shoe Review – Quality, Construction and Longevity


At first glance, I was impressed with my new boots.

They had a nice shine to them, and most importantly, Samuel Windsor hadn’t got my order wrong.

Taking them out of the box and laying them on the floor for closer inspection, I noticed that they didn’t look like they were in completely perfect condition.

There were creases and leather wrinkles in places, which detracted from the ‘prestige feel’ of the boot.


Leather wrinkles on the back of the Chelsea Boot.
The leather wrinkles.


But let’s talk about the quality of the leather.


It may be ‘Italian Leather’, but a crappy £2 fashion watch made in Switzerland can still be called ‘Swiss Made’.


Taking into account the creases and wrinkles, up close, the leather isn’t great – this is understandable for the price point though.

It is almost too naturally shiny, and I feel it looks slightly plasticky.


They claim that they use ‘premium cow hide’, whatever that means.


However, if you don’t particularly care for the details, or view the Chelsea Boots from any angle someone seeing you wearing them would, they look great, and could pass for a more expensive pair of shoes.

In other words, they may be only £50, but from afar they don’t look like cheap Chelsea Boots.


Cheap mens Chelsea Boot leather.
The leather is unnaturally shiny.


Aside from the Italian leather, the other unique selling point of these Samuel Windsor shoes is that they are ‘Goodyear Welted’, a feature of much more expensive shoes.


Goodyear Welting means that the leather upper of the shoe is stitched to the sole with thread, as opposed to being glued together with adhesive.


The advantage of this is that they are much more durable, as many stitches have to come undone for the base to fall off, and when the sole has worn away, you can take welted shoes to a cobbler and have them replace it for you, increasing the longevity.

This is compared to a glued shoe which falls apart due to weakened adhesive, which cannot be replaced.


Goodyear welt diagram.
Infographic created by Crockett and Jones.


The stitching of my shoes has been done well. It is not as neat as a pair of Clarks boots, but does have more stitches per inch.

However, some of the stitching is not visible as the leather of the shoe sole overlaps into the trench.


However, for the seemingly premium construction of this shoe to have any value, the shoes have to be worth resoling.

For the leather quality provided, I think your money would be better placed buying a pair of boots with higher leather quality, as it is probably cheaper to buy a new pair of Samuel Windsor’s shoes than repairing them.


These boots are also made in India, as are all of Samuel Windsor’s shoes.



These Samuel Windsor shoes feature leather soles with a full rubber heel.

The rubber gives you great grip, while the leather produces an elegant sound when you walk.


I have put these shoes under moderate use since I bought them about 1 year ago, and they have stood up well.


Cheap mens Chelsea Boot worn sole.


There is wear on the heel and sole as is to be expected, but I can see them going quite far before I have to have them replaced.

So, you are getting your moneys worth there.


However, I recently tried them out on a rainy day – big mistake.


Even though the rubber provides excellent grip in dry weather, I felt myself constantly micro slipping – that is, not falling over, but crapping my pants every minute or so.

On top of this, when I got to my destination and sat down, I realised that there was something off about my right shoe.

After closer inspection, I realised a small portion of the top left sole had gotten very damp and had become malleable – I could literally move it around with my fingers.


Cheap mens chelsea boot falling apart at the front.
The sole started to split apart.


When I got home and took them off, it dried hard, but was bent outwards slightly, still with a crack in them.


Samuel Windsor Quality Review

Overall, I’m going to have to give the product quality, construction and longevity of my Samuel Windsor shoes a 3/5:

  • There is room for improvement on the quality of leather used and the material of the outer sole.
  • As a plus, it is impressive that they are offering a Goodyear Welt at this price point – it is what drew me in in the first place, and a feature I couldn’t find on other cheap Chelsea Boots. Regardless of if it’s worth resoling, it is more robust than fused construction.



The shoe last is a very flattering shape and finishes about 1.5 inches past the ankle.

This ensures a clean silhouette with any trouser that you pair it with.


Samuel Windstor Prestige Chelsea Boots with a leg line.
The boots go really well with any type of chinos.


These boots also feature elastic sides. Unlike some boots, the elastic has a waffle texture. This is not visible though when you are wearing the boots.

Additionally, there is a fabric tongue attached to help you put the boots on, and a heel that will give you an extra 3cm (or 1.18 inches) of height – very nice indeed!


Overall, this shoe has a nice level of detail for its price point, so will receive a 3.5/5.



Though I have seen other reviews that say Samuel Windsor shoes come up large, these boots have a regular G fit, and are some of the best fitting shoes I have ever put on.

They were a bit hard to put on for the first time – but always have been to get off – and felt quite tight for the first few hours of wear.

But when they break in, you have enough space to not be suffocated, but not enough that you are swimming in extra space.

In this Samuel Windsor review, I would recommend you to order true to size.


I am giving the fit of these shoes a 5/5.


Samuel Windsor Review – Comfort

These shoes are comfortable too, for a Chelsea boot – but they are no trainer. Don’t expect to be running marathons in them.

Moreover, I have done some long commutes in them, and they haven’t posed the slightest problem (apart from in the rain).

They are unlined though, so if you are looking for warmth, then these are not for you.


Overall, I give the comfort for these shoes a 4/5.



I generally don’t get complements on shoes.


But these shoes are a complement beast, at least for me.


I’ve even had random people asking me where I got them from.

“Samuel Windsor”, I say. They have never heard of them – what a surprise.


 Samuel Windsor Prestige Chelsea boots on display.
They do look good.


Overall, I give these shoes a 4.5/5 on complements.


Conclusion – Samuel Windsor Shoe Review

22 / 30 – 73% APPROVAL


For the price and for daily wear, these are a good pair of men’s Chelsea boots.


However, if you are in to men’s style, or have money to spend, they don’t compare to boots available at the higher price points.

I would highly recommend purchasing these Samuel Windsor shoes if you are looking to experiment with Chelsea boots, or add them to your everyday rotation.

They are for the most part durable, look surprisingly sleek and clean well.


Conclusion – Samuel Windsor Review

As for the company, I have less kind words.


At points, my customer service experience made me feel like I was being scammed.


But if you need clothing on a budget, and are willing to risk difficulty acquiring your purchase, Samuel Windsor can be considered a good vendor. Otherwise, I would stick to perhaps pricier, but safer, alternatives, like Charles Tyrwhitt.