7 worst Chelsea boot mistakes TOO MANY guys make...

If you want a new pair of Chelsea boots, make sure you don't make one of these critical mistakes.

Chelsea boots are tricky. A lot of guys love them. And a lot of guys don't. I'm a fan of the Chelsea boot style, both for casual wear and for work.

While they're not my favorite style of boot, they're easy to throw on quickly and immediately dress up an outfit. However, you can't just wear any Chelsea boot. There are a few things to consider when picking out a pair so it matches with your outfit well.

There's a lot more to the world of men's Chelsea boots that you might not have thought of.

0:00 Mistake 1
0:58 Mistake 2
1:38 Mistake 3
4:36 Mistake 4
5:39 Mistake 5
6:40 Mistake 6
7:34 Mistake 7

#bootspy #chelseaboots

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[christianc.]

“Don’t cuff your pants”, proceeds to cuff pants throughout video.

[JCBMG]

You broke your rule. Cuffed the jeans with the casuals

[closinginonclosure]

0:47 You don't recommend wearing a certain fit because it's "not in style". I've never related to that way of thinking and living life. Having no personal identity and confidence to do what you like as an individual, but letting trends and the idea of trying to fit in and do what everyone else is doing be what dictates how you dress. That's textbook sheep/bandwagon behavior. Being a follower just isn't cool to me. I don't know if it's insecurity that makes people afraid to just wear what they like and instead let trends dictate what they wear. No personal taste but go whichever way the wind blows. It's probably insecurity and desire for acceptance manifesting. It takes confidence and security to not care about blending in with a crowd. The funny thing is, the one who walks into a room and doesn't look like every other person is the one who will actually be the most unique. And a lot of times that's where the trends are born. You'll get a celebrity who starts wearing something differently or in a way that isn't currently popular. People see it and mimic. Eventually the masses slowly start to copy and repeat until it's common. When it's common, the celebrity who is a true unique individual will recognize it's no longer unique and seek to find a new unique style they enjoy. They change and the cycle starts all over again. What it boils down to is that what's actually cool is being yourself. That's where trends are born.

To whoever read this comment. I'm sorry it was long winded and I'm not trying to be a jerk or anything. Just sharing my thoughts. I don't think anyone should let trends override what they may personally enjoy, regardless of what it is. Be a trendsetter, not a follower.

[mikethompson]

Chelsea boots are popular around the world because you can wear them as you like. Some narrower ones you can wear with a suit, or you can go casual. One of the most popular uses of these boots were as work boots such as Blundstone or RM Williams, both built to endure the toughness of the Australian Outback. I have a pair of Blundstones which I use as walking boots and they've been incredibly indestructible. I think the popularity of the boot design is down to their utilitarian nature. Apparently they were first created for Queen Victoria who wanted an easy to wear boot around the paddocks.

[richmck]

At 2min 54 you contradicted your previous comment! ( and later on in the video you showed another example…)
I’ve been wearing Chelsea boots since 1981 and the straight leg jeans or even trousers are the way to go.
And always sitting straight on the boot where the elastic ribbing is.
First rule is to weatherproof them to have the leather supple and as you say, put a shoe tree inside to keep the shape after wear.

A leather sole will wear away in bad weather and also daily use. It is advisable to get a cobbler to put rubber on them or buy them with rubber soles.
The toe should always be comfortable ( not too narrow nor wide…) never ‘’winkle pickers’’ as we used to call them when they were popular in the 1970s and I was still not old enough to wear them, according to my father!
Now to check out your next video.
Cheers!

[snalemsnolek]

3:11 so much about the jeans and Chelsea Boot thing

[whyFINAL]

If you got a chunky chelsea boot, they look good even with wider jeans or cuffed jeans! Blundstones are awesome with wider pants

[kramarbeiter]

Explains how cuffing your jeans is bad (1:34).
Proceeds to illustrate his narration with stock videos of cuffed jeans (2:55, 3:08, 3:40)

[eyang]

I think the skinny jeans still looks best with the Chelsea boots regardless.

[colinschmidt]

Cuffing your jeans with Chelsea Boots isn’t a mistake. It’s a preference.

[SniperMayer]

"Don't cuff your jeans with chelsea boots"
- proceeds to show footage 90% of which is chelsea boots worn with cuffed jeans

[antonioromulodelcarmen]

Glad to see BootSpy is making mistakes like MANY guys like us…🤦🏻‍♂️🥴

[TheXone]

You can surely cuff your jeans with chelsea boots (suede the best), however only with slim fit jeans...so in USA not common. In Europe very common.

[tbhv]

So I read a lot of different comments criticizing this video, but I just wanted to say I find your perspective on Chelseas refreshing. I personally prefer work Chelseas because I am a larger guy and they suit me better than something tailored, but you did get me thinking more about why certain styles might look more cohesive- like slimmer jeans and slimmer Chelseas. Personally I really liked the Grants Stones too but the fit seemed all off for me unfortunately. Still looking

[JediRamen]

Cuffing the jeans with you Chelsea is fire!

[Dustyfingers]

I prefer straight leg jeans that are tailored to have single break. Also have to be in shape to have the proper sleek overall silhouette

[Gabaghoul]

Please check out the chelsea boots that Tecovas offers! It has a cowboy heel so it seems like it would be a cool hybrid.

[DavidB-pijy]

I heard some advice once; never cheap out on anything that separates you from the ground. So shoes, tires, mattresses… buy something decent.

[Brownboymagic]

I have a pair of Chelsea boots with a wedge sole vibram outsole. I wear them to work

[bendatmo]

Cuffing your selvedge denim jeans with a pair of chunky Chelsea boots though. 👌🏼