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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[@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!

[@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.

[@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.

[@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).

[@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!

[@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.

[@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.

[@CademanLillywhite]

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

[@AlexGonzalez-qo7yp]

Great looks John. As always

[@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.

[@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.

[@jonro09]

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

[@seanp7871]

Chelsea boots anytime with anything 😎

[@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!

[@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.

[@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!

[@Jebro439]

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

[@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!

[@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!

[@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.

[@rajkrish9347]

Hendrix....dope 😁👌👌

[@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.

[@jimrowe4177]

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

[@richtalby5514]

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

[@40OverFashion]

Thank you Rich!

[@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.

[@danlociceroify]

Another great video. Thanks John! Stay safe.

[@c.rincon7145]

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

[@norairbadroos1558]

Always you give amazing styles

[@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. 👊🏾🧔🏾

[@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😂😂.

[@SloMoShort]

Great. Been looking for something for the olive chinos

[@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. :)

[@kevinperry3268]

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

[@hebrew80]

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

[@sanjuahmedsiam1171]

Love from Bangladesh

[@edsamson8916]

Love this vlog. Great tips!

[@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.

[@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

[@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

[@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.

[@grahamjackson1616]

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

[@dema7323]

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

[@40OverFashion]

John Henric

[@disaudio2431]

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

[@40OverFashion]

Hi Matt! They're from Thursday Boot Co.

[@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.

[@MikiBlue]

What Chelsea boots feature in this video? RM Williams?

[@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?

[@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.

[@michaelmcmanus5320]

wear them myself in fact just ordered a new pair

[@eyeheartsushi2212]

Which boots are those, John? I have a pair of dark brown Chelsea boots but they’re somewhat boring and I now realize why: the stitching is dark. If it was light stitching like your pair, they’d be more fun to wear.

[@40OverFashion]

The boots are from Thursday Boots.

[@johannalamilla6732]

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

[@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.

[@englishdave8635]

Morning John hope all is well

[@blakebiltwell5]

Keep it up!

[@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?

[@maxxsingh527]

I love you

[@127EZ]

The last one I don't like. Better with a brown color for me.

[@joebloggs619]

The Chelsea boot is so versatile, precisely because it is so plain and comfortable. They go with anything.And many women like wearing these, too. They make a statement for some older women which says "Hey, don't you dare mess with me because I know how to wear boots, too...But I am still "a lady" enough to play and have fun doing things outdoors with, that many guys enjoy..." All the women I know who like Chelsea Boots wear them either with jeans or horse riding pants or similar slacks. Or they wear them with a long casual day skirt that says "Hey, make no mistake, I am 100%heterosexual female, but I am not some dumb, useless, ultra feminine pretty little flower. I have work to do, kids to raise, family and man to care for, home to run, no matter what happens and I need strong, sturdy, comfortable, no fuss,no comments practical footwear to do all this in. Chelsea Boot is just the go. Especially in winter, where, worn with woolly Sox or thicker tights, they keep cold female legs and feet toastie warm, whilst still looking stylish, attracting no undue attention eg for looking "sexy" etc, when women have work to be got through and don't want to attract attention and distraction,because we are already too distractable, by nature, unlike highly single minded, focussed males. The young millennials like to wear these boots with short floral summer dresses, in summer or winter, with thick visible Sox. How logical is that!?! And "the look", gross and ugly as it is, costs a fortune to get. They do it largely to get male attention but say it's for liberated females' style dictum of "female comfort first". Only this look is anything but comfortable because,in winter, it is the same "bum freezer" as the 60's mini skirt or hot pants were, only they wore tall boots back then with short "bum freezer" minis and hot pants that looked sexy hot but which you basically froze in. I know,be Aude I was stupid enough in youth to wear such styles back then.Mainly because boyfriend's bought them for me and like them on me and I was to shy to refuse... On guys, they nearly always look right. One guy even wore them to a ball he took me to, with his dinner suit. He danced the night away in foot comfort he told me. Another guy I knew was pretty fussy about his foitware colour matching his pants colour. He owned several pairs of these boots and asked me to help him paint them all in various colours, to suit his trousers. The ones we dyed dark blue looked very nice with his blue jeans. But, being creative, we didn't stop at just plain conventional colours for the other pairs he had. We did marron boots and deep forest green one... Then we did two tone ones... They looked so "cool" people all wanted to know which shop he bought such trendy boots from. Eventually, we ended up painting other friends'boots as well. Having so much creative fun painting boots that we forgot why we did the first painted boots for. To go out on a date with, and have him all perfectly well coordinated, everything matching, as he liked things to be, being a perfectionist IC male personality who simply had to have blue boots to wear with his blue jeans.

[@nuradinismael9579]

👌

[@tateblaze80]

At the beginning when he said he had a confession ... My heart stopped ... Another one ? 🤷🏾‍♂️

[@lout3921]

I still can't get into these boots for some reason.

[@Pococnosurvival]

lou, I said the same thing, they are my most complimented shoes I own, from 20 year olds to 60 year olds, I have gray and brow suede and brown and black leather.

[@lanceuppercut7436]

I’m very interested in getting myself a pair of Chelsea boots, but my wife’s not keen on how they’ll look on me. Given she’s the main person i want to impress in my life, other than myself, it’s going to take a bit of convincing her. Btw, I’m not whipped, just appreciate my wife’s opinion on how i look. Got to go now, my wife’s calling...😁

[@40OverFashion]

Haha! Nice one Lance!

[@waltersickinger263]

You show a picture of Victoria in the 1800s and then someone on a horse from the 1600s.....Chelsea boots in the 17th century?

[@40OverFashion]

I just Google'd Queen Victoria.

[@spareemail8711]

Good video as always John ! on a side note do you have any thoughts on untucked shirts on men aged over 40 ? I read on a blog called www.thefortysomethingman.com that it apparently was no longer appropriate and was "immature" "juvenile" ect, I sometimes wear them untucked, not sure what to think, sorry to mention a different blog.

[@40OverFashion]

I'm okay with untucked as long as the shirt doesn't fit like a tent.

[@themancuniancandidate2744]

That's an easy one mate. If the shirt has long tails, ie a dress shirt, tuck it in every time or you'll look ridiculous. If it has short tails, ie the front and rear fall around mid crotch/arse, then it's designed to be worn tucked in or out, and in my opinion age has bugger all to do with it. I'm 51 and still wear my shirts out when I feel like it.

[@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.

[@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

[@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!

[@freddiev6050]

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

[@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.

[@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!

[@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.

[@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 !!

[@SaachinKVerma]

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

[@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.

[@rafaelmelendez1854]

I wore simular type of boots in the Navy in 1962. They were issued to the navy jackets working with oxygen bottles and these boots had steel toes. I don't think Queen Victoria nor the Beatles wore steel toe boots.

[@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.

[@DeadEyeRabbit]

Sharp!!

[@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.

[@gussy2241]

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

[@carlosmartinezjr3501]

Digging your blue squared shirt

[@emmettmarbury6571]

Man, you gotta be crazy not liking those boots.

[@GerardoHernandez-fq1mx]

What is that sweater brand? The zipper one.

[@tractorback76]

Other option than skinny pants. I cant do it.

[@parkashsingh337]

Very helpful

[@miguelpadilla31]

Great fashion tips

[@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.

[@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.

[@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

[@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!

[@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

[@MS-qg6jp]

Where do you get this Chelsea? Thursday boots?

[@40OverFashion]

Yes!

[@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.

[@markc6034]

Who makes these Chelsea boots you are wearing.

[@40OverFashion]

Thursday boot Company.

[@jarodorla6949]

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

[@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

[@kbrett2004]

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

[@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! 😀