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

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

You broke your rule. Cuffed the jeans with the casuals

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

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.

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.

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

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!

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

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

Im curious, does Chelsea boots wear or feel different than a lace up boot? Im looking into buying a Chelsea boot. I have a captain Thursday boots so i wonder if its not laced up boot then probably it will feel a little loose?

Great info thank you! opted for some other boots until budget goes from $100 to $200+

Cuffing the jeans with you Chelsea is fire!

Nice work

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

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

what shoe tree and shoe brush do you recommend?

What about the sizing ? Are they true fit cause I ware 10.5 and they are saying to down size to 10 don't want a tight fit especially paying 300$ for them

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

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.

Great video. You cuffed your Chelsea’s tho! 😅

what boots that can fit all of style?

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)

What leg opening do you recommend for Chelsea boots?

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

skinny jeans are the only jeans that go with chelsea boots imo. if you say people should not cuff their jeans, dont do it yourself when advertising a suede boot 2 minutes later in the video..

Clicked thinking this would have to do with functionality. I wish I didn't know that this existed now.

Thoughts on Seavees Beyond and Back?

WHAT COLOR boots you show in 7,20. RM Williams? but color is that burgubdy?

Alpha M says light colored pointed toe seude boots like the honey colored ones you got arent in style anymore and I have the same pair and I admit I dont really like the style on me. Should i keep them. Is he right. I want to like them i just feel like a clown.

Where's that jacket from though 👀

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

Just in time for RedWing's new release..

what are your thoughts on lu lu lemon abc pants with chelsea boots?

I just work in them like ya know boots were meant to be

When I was growing up, you never cuffed your jeans unless you wanted to get harassed.

You know that cuffed Jeans were worn probably 30 or more years before you were born. And you probably don't know one of the main reasons for the cuff pants back then during the 40's and 50's other than getting them to length. Anyone want to venture? Anyone around during that time? Nice to see that our old styles are coming back. I see a lot of styles that are coming back and the funny thing is most of the generation are thinking it's their ideas . :)

Cuffing is ok, if your jeans is narrow enough

How is it a mistake? In what universe do you get to make up the rules. Hey guys, wear whatever you want. Chelsea is a suburb of London. RM’s are riding boots.

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

There are some descent cheaper Chelsea boots . I like sonoma, chaps , Madden NYC

My almost non-existent instep prevents me from wearing anything without laces, but that RM Williams reminds me of the Caswell chukka. Beautiful. In my opinion, a work Chelsea is a contradiction of terms, like putting off road tires on a Ferrari. To each their own.

@8.36 "you dont want to condition the leather too much" is that for real? i polish my (wear every day) blundstones once a week....a pair lasts a few years.

Well we can’t have different pant lengths just for Oxford vs chelseas

I prefer baggy jeans with my boots. I just like it when my jeans cover my shoes

Much better to cuff than to have pants pooling on the boot. I find it odd that after you said to NOT cuff, you showed several clips where the pants WERE cuffed. Gotta disagree with you on this one.

The only thing I agree with is #7

So, if cuffing your jeans with your Chelsea’s, why would you show the casual Chelseas cuffed lol!!

No cuffs for real!

style and chelsea boots lol

Just wear what you like. So many rules for everything, life is already so complicated.

Whats the point in buying really nice Chelsea boots and no one can see them because your jeans are over them? Team skinny jeans + cuffing

R M Williams vs. the Grant Stone Chelsea Boot. The Grant is a little more affordable. Cheers..

This guy said Chelsea more times than a girl named Chelsea... 😂

Don't cuff your jeans, period. Get them hemmed like a normal adult person.

I’m suspicious about using shoe trees in Chelseas for fear they could stretch the boots and fit looser, or driving with Chelseas and stretching the elastic, what do you folks think? Am I overly cautious? Thanks

This video showcases his worst nightmare... Cuffed Jeans

Make up your mind with the cuffing

What jeans should i wear with these boots.. Congrats if thats your biggest worry or decision to make right now 😂

Baggy jeans are rubbish, im sticking with skinny jeans

Mistake no 8 - watching this ......

The fact that there has to be a video about what pair of jeans to wear with a boot tells alot about the world today

this guy needs to update his channel name as Dress Boot Spy at least...

Skinny fit jeans are not my deal!!! Slightly tapered jeans at the bottom are great!!! No cuffs at the bottom period!!!! 😎😎

Saying a Chelsea boot is not a “manly” look is just silly and born out of insecurity. A bulky Chelsea like the Red Wing with a looser fitting jean cuffed to almost the top of the boot is a super popular look in Chicago and I think, pure fire.

Too many years wearing western boots. You’re not getting me into skinny leg openings or tapered anything.

most of these are pretty opinionated, i personally think wider jeans and cuffs look great with most chelseas, if anything the mistake is wearing jeans with a pair of slim dress chelseas

"mistake" lol. more like personal opinion.

Men wearing boots named "Chelsea".

I have to disagree with you on the cuffing part.

Unless your Huckleberry Finn, never cuff your pants!

Is buying Chelsea boots not a mistake in itself?

Tells not to cuff and then shows multiple videos with cuffed trousers. Wow.

Why not skinny jeans/pants over Chelsea ?

Wearing them in the first place!

Definitely disagree :)

Keep working-never wear the same pair of shoes (or boots) 2 days in a row

Wearing any type of Chelseas is an abomination.

Told people not to role yp your jeans.. in every video guy had his jeans roled up? Cuffed up 2 shit

Never take amphetamine 😂

Your equipment is too small if you need the shoes to be seen this badly. Quality shoes need to be heard not seen.

The first mistake is wearing Chelsea boots.

The only real mistake is being a slave to fashion. Be yourself. Wear what you like. Don' t act like a lemming.

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Just wear shorts, problem solved!

Ha ha, stick to what you said as is your preference or choice. Your preference or choice doesn't mean to say it will look bad just because you say so. Your far from the guru of chelsea boots, especially for European fashion!

No cuffing your pants. It’s a terrible look. My girl friends literally always make fun of them.

Rule that they brake; No1 ) wear them...

Number 1 most common mistake when wearing Chelsea boots is wearing Chelsea boots

Men don't wear these.

The biggest mistake is buying them.

Do you hate your audience?

the only chelsea boot mistake is buying chelsea boots..

chelsea boots are very feminine, & your styling tips are too

Number 1 on this list should have been: buying a Chelsea boot.

this may be the gayest video ever.

In my opinion, the Chelsea boot itself is a mistake.

Chelsea boots are a poormans boot design

Is it just me, or Chelsea boots just kinda feminine looking.

Buy, this style of boot is a mistake. They are so ugly!!!