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

[@christianc.1550]

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

[@FutureMemories1983]

Was literally coming here to say that 😂

[@ChristopherReyne]

Don't you ever tell anyone not to cuff their jeans with Chelseas. That is pure and utter nonsense. 😂

[@run4cover32]

😅😅

[@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.

[@richmck007]

It’s other people dictating to you telling how you should and should not wear something like these boots that creates an uncertainty in people’s minds. I agree with your mindset. WEAR it as you see it and not be dictated to by others. Each one teach one by leading by their own example! Amen.

[@closinginonclosure]

@@richmck007 Exactly, my friend. It's unfortunate that it creates uncertainty in some people's minds. And even more unfortunate is that some people are so in the weeds with following which ever way the wind blows, that they can lose touch with who they really are as an individual. They can lose personal identity and become more of a chameleon. We're obviously talking about style and clothing, but this bleeds into all aspects of people's lives. From political choices based solely on what's most predominant in the area they live and those around them, sports teams they support, music they listen to, and countless other things. It's a shame that more people can't just be themselves and not let trends dictate their choices or make certain decisions just because it's what the majority is doing. That's a hollow, unfulfilling, and a bit of a phony existence to me.

[@richmck007]

@@closinginonclosure life is short, love the life you live and live the life you love! My mental philosophy on life’s choices. I agree again with your fine words. 👍🏼

[@scottc77]

I wear skinny jeans with my Chelsea’s and boot cut with my Redwing moc toes and no I never cuff my jeans and IDGAF what other people thjnk

[@richmck007]

@@scottc77 Amen to that!

[@JCBMG]

You broke your rule. Cuffed the jeans with the casuals

[@Trollzrule]

He said it himself in the video

[@tanyanglali3126]

I guess he means leather boots . not sued one

[@elliottk2518]

Haha

[@Hellgrinde]

Yeah he literally busts himself and goes to jail for it in the video haha

[@benjohnson423]

He doesn't scream, "i know what really work is" does he. Mr rolled up jeans.....

[@mikethompson3305]

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.

[@whyFINAL]

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

[@richmck007]

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!

[@Jim_Buck]

I used to wear Chelsea Boots but the lack of any grip isn't great in UK winters

[@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

[@inzendio]

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

[@colinschmidt3475]

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

[@BlenderShipyard]

Can anybody recommend a replacement for Blundtstones? I used to love them, but their sizing has changed and don't match my feet anymore. Also, just had the soles on a recent pair crack for the first time! Different rubber?

[@michaelstecyk7365]

Blundstoes have become bad

[@snalemsnolek1539]

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

[@miguelteran-raful2718]

What leg opening do you recommend for Chelsea boots?

[@jordyalmonte42]

He recommended slim/tapered fit. You wanna show off the boot

[@42Deckhand]

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

[@DG1965]

...ladies? 😂

[@countvertigo1788]

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?

[@Peapodzilla]

Thoughts on Seavees Beyond and Back?

[@laforminc]

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

[@sadikmakwela1255]

Could someone tell me what kind of shirt he is wearing. I've been looking for those types of shirts for a while now i can't find them. Please help.

[@ernesthenderson981]

I've worn Redbacks for years. The most common mistake I've made wearing them is that I forget to put on socks. The solution is to sleep in a pair of socks, which gives you a jump start on your day as soon as you wake up. The downside is you have to sleep in a pair of socks.

[@maggotsyt2647]

what boots that can fit all of style?

[@eyang7]

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

[@CogMarks]

…if one has the body for skinny jeans. I was thrilled to see skinny jeans go out of style, because the only people who fit in them well was middle school age girls.

[@LeonExile05]

Slim proportions a bit better and the taper on the ankle as well. I for instance go for 32 waist and 30 length as it hits just the ankle for me. I was doing 32x32 for the longest time or 34x32 when I got more chunky, but I only do 30 length now and I find it much better.

[@handsvsfood2781]

Men wear slim or straight fit.

[@ralph7077]

I think the skinny jeans should be banned on guys, except if you have really skinny legs.

[@rickdoehler502]

as long as you can get the jeans over the boots. F' I through them on if they are not perfect, so be it. These care casual boots in their dressiest form

[@SomeVagrant]

The only chelseas I'll wear are the work wear type and I swear by cuffed, tapered/slim jeans for those. They're never going to look sleek and trying to achieve a sleek look will just make it look off. Imo, you kind of need to embrace the ruggedness by showing off the creases and scratches, and highlighting the likely slightly wider fit at the upper end of the shaft. I especially love that look in fall/winter with a pair of thick woolen socks peeking out. Looks sort of lumberjack chique or something.

[@spongey747]

what shoe tree and shoe brush do you recommend?

[@quickaddress204]

Where's that jacket from though 👀

[@SniperMayer]

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

[@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

[@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)

[@GyudonDream]

Cuffing the jeans with you Chelsea is fire!

[@AndyPak-138]

What model is the Bored on Columbia.

[@wulfsnack3594]

Bordon Columbia (had to use CC lol) Isidro Chelsea in Burgundy

[@garagegorilla5x5]

I have a pair of Chelsea boots and they're so stiff I can't even get my foot in them. 😂Yes I'm a noob. What should I do to fix this?

[@tinman3505]

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 . :)

[@brad1574]

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.

[@maxsweet]

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.

[@xGETitHOTx]

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

[@yesmichaels4571]

really?

[@azaankhan1174]

U keep on saying dont wear folded bottom jeans of cuffed jeans and showing the model again n again wearing cuffed jeans 😂😂😂

[@B501R]

Yeah he is an oaf youtuber.

[@jasonpettis4691]

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

[@rickallen9099]

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

[@darylporter4290]

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.

[@rpow6861]

Pin rolled to the top of the boot looks awesome, end of story

[@JPK1337]

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..

[@MaxSphynxEgo]

Exactly ! The whole point in wearing Chelsea boots is to show them off !!

[@guillermomaciasrojas7912]

I guess you didn't watch the video

[@Gabaghoul0000]

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

[@LightsOutPredatorRemoval]

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

[@iamcomanche9184]

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

[@kathleenr744]

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

[@jasonkrasowski4673]

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.

[@antonioromulodelcarmen283]

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

[@BootSpy]

I don’t make mistakes

[@Slyma17]

@@BootSpy makes manstakes

[@Bob-l4q6f]

​@@BootSpy- What do you think about the Rodd and Gunn men's Port Chalmers Chelsea boots?

[@Indy1701e]

Cuffing is ok, if your jeans is narrow enough

[@bendatmo]

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

[@fallingwickets]

@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.

[@plugangmor344]

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

[@amitrana3302]

Nice work

[@adamp5951]

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.

[@awdtw]

Jodhpur / Chelsea boots are common as dirt here in Australia as work boots, from livestock to concreters and construction. Rare to see a chisel toe in the work place, but very common around livestock folk. Round / almond toe very common in construction. Never actually seen a concreter wearing a lace up boot, likely because they can swap between work boot and gum/muck boots easily. Rossi, Blundstone, Redback and RM Williams, all good to go here in Australia. RM Williams gardner with commando sole is my go to work boot.

[@KalbiKing]

If you ever go to Australia, look at all the tradies working. They're pretty much all rocking blundstones to work.

[@mikethompson3305]

Chelsea boots were originally created as work boots for paddock duty. And they are commonly used for work and casual purposes all over the world.

[@robertrichter7702]

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

[@johnh5660]

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

[@mekko1413]

Too wide of a pant is not a mistake. Only skinny jean fashion nerds think that. I thought this was going to be actual mistakes. I didn't see one actual mistake just subjective city fashion BS until like 8:32 or so. The full 10min should have been on how to care for your boots and the mistakes around that. The rest were not mistakes just fashion garbage.

[@peterhess2610]

I got a pair of Chelsea’s from Thursday boots. Great boot-too bad the company has gotten really shitty.

[@albertoclonado]

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

[@yme3267]

Yeah man. You're over thinking it haha I have boot shoe tress from Thursday boots. Really great! Not an add for Thursday. They're just cedar and were easy to find lol

[@awdtw]

Tree's are a must for my chelseas. The area just behind the toe wants to drop unless it is supported. People who don't want to shell out for actual wood tree's should at the very least use paper or something to give the boot some fill when not in use.

[@steveedwards8490]

I use the plastic DASCO shoe trees. They work fine and help keep the shape of your boots. The boots don't stretch.

[@ProduceDelicious]

Tells people cuffing looks bad w/ Chelsea's. Proceeds to show off literally every type of boot with cuffed jeans... low effort

[@reardelt]

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

[@Andreesss]

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

[@Kali-nl3ll]

i think it would look absolutely great with a pair of shorts....any shorts is fine...

[@jamiegore4192]

A real man aint worried about this crap to start with especially cuffing or rolling up the cuff of your jeans ....every time i see a guy wearing a fitted pair of jeans and has the cuff rolled up makes me second guess him to put it in a polite way lol

[@Andrew_Lewis]

The only thing I agree with is #7

[@TheBILLIARMSTRONG]

came her cuz im getting new boots for work not extra work on taking care of them . this guy is fruty .

[@danielhonkialeechan9744]

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

[@markdunn1931]

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

[@andrew1212w]

You just said never cuff jeans with a Chelsea boot then show a photo of a suede boot with cuffed jeans.

[@alessandrosestili1380]

Mistake number 2: Done short your jeans All picture has jeans been folded

[@parkerjonesjr]

Just in time for RedWing's new release..

[@tikiortaka]

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

[@robligeti8353]

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

[@Madanth0ny]

You lost me when you said don’t cuff with a Chelsea boot …that’s when you cuff them bud

[@vnm_8945]

style and chelsea boots lol

[@williamolliges2622]

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

[@pauljohnson3686]

This video showcases his worst nightmare... Cuffed Jeans

[@dsigner]

these are not mistakes. these are choices. number 1 is not that wrong.

[@angelo-001]

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

[@Regretfulloon43]

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

[@abelprado7921]

Opinions. It’s not a mistake… it’s just what you prefer. Stop assuming or convincing yourself you’re an expert.

[@FRD-HDD]

Wearing any type of Chelseas is an abomination.

[@ijuswannaluv]

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

[@SpiceAndSauce]

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

[@TopMale]

No cuffs for real!

[@scottjohnson676]

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

[@javiervelasquez6478]

Chelsea boots look way better with boot cut jeans. They look Wack with tapered Jeans 😂.

[@maxfalconi6995]

As much as I wanted to "like" Chelsea boots... I simply can't

[@hectormerc350]

Make up your mind with the cuffing

[@jmac321]

Unless your Huckleberry Finn, never cuff your pants!

[@ResistenciaRasta]

im more confused than I was before watching this video

[@Erd_Geschoss]

"mistake" lol. more like personal opinion.

[@justinmora4181]

Mistake #8 - worrying about how you look with your boots.

[@kukmisu]

Do what you want.

[@joe-nn2ml]

Cuffing your pants went out of style in the 1950's

[@Mr_tickets]

Baggy jeans are rubbish, im sticking with skinny jeans

[@miravlix]

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

[@V0L4T1L3]

He lost me when he said his fav boot was a Comfort Craftsman from RM. 🤮

[@hiteshahir2671]

Why not skinny jeans/pants over Chelsea ?

[@bigboycreams4769]

People seem to think you aren't allowed to wear skinny jeans anymore. Of course spray on jeans are very ugly but if you have slim legs then skinny jeans would look great.

[@remington_acr1651]

@@bigboycreams4769absolutely. Especially if they compliment your body type. Nothing wrong with a good pair of quality skinny jeans.

[@krystianxmuszynski]

Brah, my friend got outstanding suede Chelsea boots, better looking than your suedes by the way, for 13 dollars

[@JayRivera-j3v]

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

[@matthewshipman1932]

1st mistake is wearing boots with a girl name..it's got to be a manlaw..I just picture two dudes riding on a Vespa together