How to Style Chelsea Boots | 4 Casual Ways

Gentlemen, I filmed this video before all of the quarantine madness, so please be aware of that when I make reference to going out to lunch & dinner. Today I'm showing you 4 different ways I personally like to style dark brown Chelsea boots for casual situations.
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[@alonzocalvillo6702]

I admire you for not dying your hair.I lot of guys think that dying ones hair will make them look young, no , they look like someone trying to look young. Leave that for the women.

[@barrya7652]

The line “you’re never too old to make a new change or to try something new” has become my mantra. I’m close to 65 but your videos have inspired me to change my look and try a more modern and younger look in the office. People have noticed and I really feel more engaged with the younger cohort. Great to see you back producing new content since your “true confessions” video a few days ago. Keep producing your excellent content. We’re watching!!

[@40OverFashion]

Thank you Barry!

[@johnjames218]

I have been wearing Chelsea boots since the late 70’s, at present I own a pair of tan suede Chelsea boots, a black leather pair and a brown leather pair, they are fantastic.

[@Sams911]

I started out with RM Williams, from a trip I did to Australia and fell in love with the style and quality of these... now I own a pair from John Lobb, and Gaziano & Girling and they're my "Go to" boot for casually/dressy look... jeans, even causal suit / no tie.. works great.

[@nottsforest69]

I liked the simplicity of this video showcasing the versatility of the Chelsea boot. One of my favorites. Thanks John.

[@40OverFashion]

Thank you for commenting Andrew!

[@gregturbeville7904]

Great looking outfits. As an older guy, i am always looking for ideas to help my outfits. Glad you are back. Keep the content coming

[@stanislas4990]

Great outfits, so elegant. I especially like Chelsea boots with jeans of any color. Chelsea boots are the perfect casual shoes (with loafers and sneakers).

[@jimyoung9262]

I was going to make a joke about rocking this look in my quarantine house, but instead let me say good video and I hope everyone out there is staying safe.

[@loki2240]

Yeah, I've been stuck in my house, wearing athletic shorts or sweats for over a week. Stay safe, everyone.

[@IdrisFashan]

Don’t let a global shutdown keep you in your pjs gents! Rocking my varvatos polo, killer jeans and chrono vintage watch on Sunday... what’s good, y’all. Monday I’ll be stepping it up-from home. 👊🏾🧔🏾

[@CademanLillywhite]

Dudeee that last look with the olive chinos was absolutely killer 😍

[@e.j.volkman7394]

Alright, you convinced me. Time to slow down on the whole “bright colored athletic shoe” and into some Chelsea boot. Only took about 2 months of watching your videos 😝

[@splitfinger7719]

Lmao I’m there as well

[@kbrett2004]

Thank you for putting out content for us during this time. It is very much appreciated

[@allanhunkin7617]

Just recently bought my first pair of Chelsea boots. This video is bang on target on how best to wear them. Thanks John😁🤛

[@40OverFashion]

Thank you Allan!

[@AlexGonzalez-qo7yp]

Great looks John. As always

[@Bk-ks4dr]

the most class color combo i have ever seen , u made my wearing , thank you!!!!

[@michaelgayle6405]

I absolutely love the look the Chelsea boot gives an outfit. I don’t own a pair yet, but they are on my list of shoes to purchase. Thanks again for the great contents you have on your channel!

[@danlociceroify]

Another great video. Thanks John! Stay safe.

[@brandonsmith479]

I was skeptical of Chelsea boots as well. Bought a pair though and absolutely love them. I still like my chuka boots more but the easy slip on Chelsea boots are great. Love the style options you mentioned. All them are fantastic looks.

[@ronm6585]

Great looks John. Thanks.

[@norairbadroos1558]

Always you give amazing styles

[@jonro09]

Great info as usual and as I have just ( yesterday) bought some Chelsea boots -:)...perfect timing.

[@miguelpadilla31]

Great fashion tips

[@seanp7871]

Chelsea boots anytime with anything 😎

[@joemizz11]

John, not every day where you can learn fashion & history, very nice touch 👍 I currently don’t own a pair. However I’m now going to look at them. Thank You. Great Vid

[@ianrobinson5841]

I own 4 pairs of these type of boots you just can't go wrong! As long as the trousers you wear are narrow at the ankle like you showed they look good with anything! Great vid👍

[@holoholohaolenokaoi2299]

i rock my chelseas with corduroy birdwell beach shorts and hibiscus print aloha shirt. chicks dig it!

[@edsamson8916]

Love this vlog. Great tips!

[@jobro524]

Nice look-book Loved the way you pair the shoes with the outfits

[@bhar48204]

I've never personally liked Chelsea boots, but they look good on you. I also liked your shirt at the beginning, and the end-cuff jean roll-up.

[@c.rincon7145]

Excellent video !! I can use all those styles and will !! Thanks so much !!! Stay safe !

[@cosmicsailor6918]

Chelsea boots give a nice sleek casual look. And are easy to put on and out.

[@jameshaddan8538]

I have a couple of pairs - brown suede and black. They are my favorites, absolutely indispensable, especially when traveling.

[@keithosorio8598]

I have the exact reaction you had to Chelsea boots. I bought a tan leather pair because it seemed like everyone was recommending them. I think I’ve worn them twice. I loved all the looks you showed and will definitely give the boots another shot when we are released from our social distancing situation.

[@1975lgpascal]

Great combination 😍

[@carlosmartinezjr3501]

Digging your blue squared shirt

[@SaachinKVerma]

Hey! Man, i wanna tell you. You should post video every day. Love to see your video.

[@AisleorWindow]

I'm a new convert to the Chelsea as well. Love mine that I got a couple of months ago and wear them with a suit and with jeans. So versatile.

[@jeffdallen6445]

Nicely done. That last outfit was spot on and makes me think you could do a video on the versatility of olive chinos as well.

[@paulalaye6428]

Hey John loving the pale blue shirt at the beginning of the video, loving the olive chinos too, very nice... Keep smiling Paula x

[@themancuniancandidate2744]

I am a huge Chelsea boot fan. Growing up in the UK and moving to Australia, they are super popular in both countries. They can be worn with jeans/boots/pants, and their versatility is probably my favourite thing about them. Superdry sell very good quality Chelseas at around the $95 mark, and they are really good value. Which is what I tell my better half when I come home with yet another pair. Great video, as always. The phrase "All dressed up and nowhere to go" has never been more apt.

[@freddiev6050]

I luv chelseas & chukkas myself! I find them to be "a medium" between shoes & sneakers. 👍

[@EmperorOfSomething]

Damn, all of the outfits were quite nice! I'll be looking to try out some muted florals soon. But that double zipper sweater is !!

[@parkashsingh337]

Very helpful

[@David-wo9un]

Nice looking boots!

[@jeffmullan8206]

I have blue suede Chelsea boots and I love them.

[@rajkrish9347]

Hendrix....dope 😁👌👌

[@YuSuck]

Great. Been looking for something for the olive chinos

[@richtalby5514]

Good look book and liking your channel. Thanks and appreciated.

[@40OverFashion]

Thank you Rich!

[@ianmackenzie686]

Nice vid. I may just invest in a pair of these myself. And a soon as there is someplace open to go, I'm there! 😀

[@boomdizzle87]

Olive Chinos are some of my favorite things to wear in general but especially with Chelsea boots. A lot of times with a VERY similar jacket as look 4; have never paired it with a dark shirt like in this look but might give it a try now.

[@DeadEyeRabbit]

Sharp!!

[@kevinperry3268]

Love myself love my Chelsea boots do a lot of things with him 👌

[@davidbuxton7921]

I’ve always had a problem with Chelsea boots mainly getting them on and off due to a high instep. However I really like the look so I purchased a grey suede pair , I think they look great! Well worth the struggle getting them on and off! They are so comfortable and stylish and go with just about anything. I also now own a second pair in suede ,a fawn colour, they are so versatile and can also be matched with a variety of my wardrobe. Hope you are well and getting over your troubles,thanks for all your great advice!

[@MarcMoore]

Great video my friend. I don't own any Chelsea boots but between you and Steve at "The Dapper Aristocrat" I just might buy some.

[@blakebiltwell5]

Keep it up!

[@victoryveshinojosa]

I love chelsea boots and have 4 pairs. My favorite by far are my RM Williams Comfort Craftsman. I highly recommend them and suggest to find a slightly used pair on eBay like I did. Unfortunately, brand new they are now $500+ since LVMH Group (Louis Vuitton Moet Hennesy) bought the company and turned RM Williams into a "luxury brand". They used to be $300+- or so before LVMH. No way they are luxury boots but they are sharp looking, comfortable to wear and are rebuild-able. That being said, I own a pair of tan suede chelsea boots that I found at Goodwill for $7 that get many compliments too.

[@willlevine9692]

Victor Hinojosa I have been to a retail location and tried on a few. Exceptionally made. Alas the price point too high for me.

[@jay-rus4437]

Wasnt a fan early on as I added to my casual wardrobe for taking the wife out on Friday or Saturday nights. HOWEVER…..now they are my favorite. My preferences in order are Chelsea, Chukka, and then a Wingtip Lace (preferably with inside zipper. Then most of the time I wear dark jeans and a simple dark long sleeved shirt with some type of subtle design in the material or possibly a small pinstripe. For my date coat, during fall/winter, I like a classic black P-coat. And then to top it off with a flatcap. So there is my lineup for date night. Im a General Contractor, so I felt like it was important for my wife not to have me go out in my typical daily carpenter pants and flannel 😁

[@40OverFashion]

Well done!

[@jimrowe4177]

I picked up a pair that have the brown fade effect. They're my most complemented footwear.

[@BobsCreativeDays]

Love the looks. Would love to wear Chelsea Boots but I have a wide foot with a very high arch so any non-laced boot or shoe is always painful to wear. Great looks that will look great with whatever footwear you choose.

[@maxwrestling1278]

Glad to see you Brother. All the way from Germany. Keep going! I know you will make it ! If you are ever in Germany, hit me up.

[@grahamjackson1616]

Thank you, great styling, & terrific with Cuban heels,,,, mmmmm

[@ApparitionRune]

I'm catching this video a bit late but love the video. You should get a pair of carmina chelsea boots. They are a bit spendy but worth it.

[@67spankadelik]

John if you ever into the market for getting a more dressier Chelsea boot I would recommend Ace Mark and Thomas bird of London. I own several from each brand and they are an excellent value at the price.

[@sanjuahmedsiam1171]

Love from Bangladesh

[@maxbokol]

I love the black denim jeans with black sweater. Got these all covered. Now, all I have to do is look like John, lol😂😂.

[@bernardtan1]

Best thing about Chelsea is that there's no need to tie shoelaces just slip them on & off they are so convenient plus they look like no other shoes.

[@jacksoncrow7662]

Hi Jon, been wearing Brown Chelseas for 6 months now. They go with everything but need avoid the cheaper versions as they can look bad!

[@jarodorla6949]

I liked the green chinos dark blue shirt and blue overcoat with the boots I'm 42 & that's exactly I roll

[@maxxsingh527]

I love you

[@ttop64]

I have a pair of black and camel brown leather Chelsea boots and just recently picked up a pair of grey suede ones. I would eventually like to find a pair of tan ones. I like them for their good looks and versatility. BTW I also have a vintage pair of Chelseas from the 60's but feel the cuban heels are a little bit too high to wear these days. Have a great day John and stay safe and well. Peace. :)

[@frankm4486]

John, I recently watched your video where you told your story of the financial hardship you went though. I can't tell you how much respect I give you for doing so. My name is Frank and I am 51 years old. and I still don't know what I want to be when I grow up. I hold a steady job that I can tolerate, for the past 14 years. Although I have many interests, men's style is one of them, I just cant seem to find the... signal... for lack of a better word that tells me ok this is what I should do...go!! Anyway, I'm just writing you to let you know your not alone. There's a lot of guys like us out there. I love your video's and think your doing a great job. In my opinion your Very successful. God bless you my friend

[@40OverFashion]

Thank you very much Frank! I'm glad you're here.

[@hebrew80]

hi tnx for the video. Request you to please add the brand of the chelsea boot you are wearing with a link please

[@ricklogan3006]

Can you tell us where you got the boots you are wearing, i think they are great, can't seem to find anything that really looks like these, thanks

[@englishdave8635]

Morning John hope all is well

[@gussy2241]

Where did you get that nice zip up sweater? What size? Great channel!

[@jamesmeyer2365]

Great video. What your thoughts on the dress Chelsea boots? Color? Brand? Thanks!

[@40OverFashion]

Thanks James! I only have this one pair from Thursday Boot and I really like them. I also think this dark brown is very versatile.

[@jamilwehbe6945]

I loved the green olive chino a lot . Do you agree me if suits with a dark brown shirt or better with black. All the best.

[@40OverFashion]

I guess it depends on the suit color, but black is very universal.

[@fredfarrell5]

hey the chelsea boot...... im not a fan..... until i picked up a pairs .. omg love them got my first pairs at costco all leather only $45 ,,, now i wished i got 4 pairs... Alfa M thank you,,, lol

[@Deadlyfinisher09]

Hi, can you tell me what width the bottom of leg is on the jeans? They look like a nice fit over the boot, thanks.

[@michaelmcmanus5320]

wear them myself in fact just ordered a new pair

[@mcbacino]

Love that overcoat! Who makes it? Great video, thx John.

[@40OverFashion]

Thanks! It's from Everlane.

[@andrew1212w]

Nice video! I own 2 pairs of Chelsea Boots one pair by Geox and the second by John Lewis (UK Store) I tend to wear them during the Fall and Winter months 😊

[@PB-np4nm]

andrew kelly Are the JL boots good quality for the price?

[@andrew1212w]

They cost £85 dark brown leather upper with synthetic sole size 9 (43) bought last December very good for the money - check out the John Lewis website.

[@matteng4216]

Great looks! What brand of Chelsea boots were featured in this video?

[@40OverFashion]

Hi Matt! They're from Thursday Boot Co.

[@LowdenFretter]

Great video as always John. A little off topic but did someone already win the Daniel George free suit thing?

[@40OverFashion]

Yes! Daniel’s staff is handling it.

[@dema7323]

may I know which brand is the textured zip sweater? Great video thanks!

[@40OverFashion]

John Henric

[@GerardoHernandez-fq1mx]

What is that sweater brand? The zipper one.

[@willlevine9692]

Hey John, thanks for the styling ideas. I have a pair of dark grey suede and dark brown suede both from Thursday Boots. Both are Cavaliers. Question, how do you feel about wearing suede with cords?

[@dylanlundgren]

Will Levine Hey man, question for ya. I usually go down a full size in Thursday boots, and I actually snagged the same grey suede cavaliers off of eBay. I feel like they are way slimmer than any of their other models. Did you find this to be the case? I’ll likely only go down half a size for when I pull the trigger on a new pair.

[@willlevine9692]

Dylan Lundgren Hey Dylan. I had quite the time dealing with Thursday Boots as their customer service was not spectacular. I had originally ordered the Dukes. They suggest sizing half a size down from sneakers. So, I ordered a 7 1/2 which was way too big. Exchanged them for a size 7, which was still too big. Then I exchanged them for a 6 1/2, which was too small. I finally got someone on the phone who suggested I try the Cavalier because I have a narrow foot and ordered them in size 7 which fit and subsequently ordered the second pair. They are slimmer and I like that styling. Do I wish they had a pull tab, yes, but I enjoy wearing them. I wish I wore them more but I seem to find myself wearing my white sneakers more often because I seem to be really casual these days. But I will try to wear them more often. I also have a pair of brown leather chukka boots by Clark I enjoy wearing. Stay safe out there.

[@nuradinismael9579]

👌

[@shaunleonard3878]

John, how did your surgery go? How’s your recovery going? Hope everything went / is going well!

[@40OverFashion]

My surgery was cancelled. Thanks for asking.

[@MikiBlue]

What Chelsea boots feature in this video? RM Williams?

[@DrewHen]

What brand are those??

[@maxbokol]

Hi John. I've been looking around for something similar to your dark brown Chelsea boots. Do you remember where you got those? I really want a pair, lol. Thank you!!

[@40OverFashion]

Thanks! They’re from Thursday Boots.

[@maxbokol]

@@40OverFashion Thank you so, so much for responding. I appreciate the help very much. Please, continue what you do, a great help to many of us.

[@q-storm767]

I use to have a pair of Chelsea boots but lost interest and gave them away. Maybe one day I will gain interest again and purchase a pair.

[@kentsou399]

Do you wear skinny or slim jeans?

[@johannalamilla6732]

Me hubiera gustado indiques el problema que hay cuando te sientas porque al levantarte el pantalón Chinos queda terrible enganchado en la Chelsea

[@Stophey]

Are those chelsea boots in your video from Thursday Boot Company, by any chance?

[@40OverFashion]

Yes they are!

[@Stophey]

@@40OverFashion I have the same pair, and I absolutely love them. They're so versatile. Easy to dress up, but with just enough little details to make them a great choice for casual wear too. Very comfortable, but they were very snug while I was breaking them in. I'm a big Thursday fan. Just bought a pair of brown suede harness boots from them, and while I haven't had the chance to wear them much yet (thanks, coronavirus!), they are gorgeous to look at. Do you have any videos on proper shoe and boot care, breaking them in, using brushes and trees, etc?

[@phillipmoodie9071]

Now that you've decided to get with a classic style boot why not lift it up a grade by looking at the Australian stockman's working boot made by R M Williams. While it has become a fashion boot during the last few years, they are repaired by the Australian factory and will last for decades. Phil.

[@robertrivas6159]

Are there any particularly good brands you would recommend?

[@40OverFashion]

These are from Thursday Boots and they're great. I don't have personal experience with another brand.

[@kevd6034]

I tried these but the bottom of my Jean's kept riding above them. I prefer the skinny slim fit so the boots had to go. Yiu make them look good though

[@glennmoonpatrol8676]

What about wider legs on the pants? Are these boots limited to tight pant cuffs?

[@40OverFashion]

Personally, I like a more tapered fit, but that's not to say a slighter wider leg wouldn't look great too!

[@DeadEyeRabbit]

The denim jeans. What brands and styles.

[@JoelGonzalez-ud7qo]

Agree, need to know what jeans those are that have the proper circumference at the hem. Thanks John.

[@40OverFashion]

Lighter wash are from American Eagle and the dark denim are from Peter Manning.

[@Newbill17]

Those outfit ideas all look great. I stick with the solid colors and some classic thin pinstripe shirts but that’s just me. The length of all the pants work well with the boot. I wish I could wear that style of boot but I stick with chukkas because I have freakishly thin feet and have to tie up for a decent fit. The dark brown boots look just right, stylish and versatile. Those boots are made for walkin’ John, and I could use a long walk right now. Thanks for another great video.