How To Wear Your Boots With Chinos and Jeans

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[@rolandboss9045]

Chelsea boots are the best for me.

[@saadbandaralgayla3849]

chelsea boot good for 5.8 up but if your short guy not for you...

[@00sra]

I recently ordered the President Thursday boots! That’s why I’m watching this great video! 👍

[@ehJoe]

Thursdays look great, i dont normally roll the pant leg but will be trying this, thanks for demostrating the different looks.

[@40OverFashion]

Thanks for watching Joe!

[@englishdave8635]

Love me some Thursdays I have Dukes Captains, Scouts and Lincoln's. Great vid John and as always great to see you

[@40OverFashion]

Thank you very much Dave!

[@Ferien7]

English Dave how are the Thursdays holding up?

[@englishdave8635]

@@Ferien7 real good had them about 4 months brought them all this year

[@Thursdayboots]

@EnglishDave You're the real MVP :)

[@alponca5943]

Great video and tips John! So many of us live in either jeans or chinos and changing the shoes/booties helps to either update or refresh. Thanks for loving what you do and share it through your channel!

[@40OverFashion]

Thank you Al!

[@robyoungquist5803]

Almost ordered from Thursday but at the time they didn’t have what I wanted. I, by happenstance, decided to stop in at Johnston and Murphy and low and behold viola … perfect boot in my size and color I wanted. Two wearing sandals they were “broken in”. Got so many compliments from both Nursing Staff and Patients when I’d wear them. My second pair I got from Beckett Simonon. Those are custom made boots at an affordable $200 but they came with a 3 month wait which I was ok with. OMG the premium leather is really unbelievable! And COMFORTABLE. Thanks John for this presentation … I’m a bit wonky on the rolling part but it’ll come. 🤷‍♂️. Still too hot to worry about fall clothes and boots when today’s (9/22) high in Pasadena is going to be 95F. 🙄. (Legend)

[@40OverFashion]

I hear you. 102 in Temecula!

[@niceguy5430]

In my experience Brown and grey Swede boots,looks great....

[@40OverFashion]

I agree! Thanks!

[@aseemb85]

I am 5.4 and ever since looking for something helpful like this. Thank you for tje video

[@40OverFashion]

Thanks for your comment!

[@Larry-qz3es]

I own a pair of their Tobacco Stateman's with a matching belt. Awesome shoes and they recommend that you purchase a size 1/2 the size you normally wear. My plan is to purchase the Duke Chelsea boot.

[@40OverFashion]

Great boots Larry!

[@JoelGonzalez-ud7qo]

Love the look of suede, but my horrible walking habits cause scuffs/ scratches easily. I bought the caramel cadet and can't wait! Thanks John!

[@40OverFashion]

Thank you for your comment Joel!

[@roliver7773]

Nothing says "rugged man" like tapered jeans with a roll.

[@pastorcharliehernandez4017]

Well as you may know, we are about to get hit by hurricane Dorian… So depending on the outcome I’ll be heading to the store to check out those boots. They look great. Wish us luck down here in Orlando Florida. Thank you John again for another great video.

[@40OverFashion]

Stay safe my friend!

[@wakeupbreathing]

I usually go with the “no break” or a really small break look. The exception is when I am wearing western style boots. These require a bit more break or it looks like your jeans are too short. I’m not a cuff guy but if you can carry it off go for it. Thanks John!

[@40OverFashion]

Thanks for your comment Steve! Great meeting you at the meetup!

[@rheamorales1329]

Great to see you again, John. Not all women prefer skyscraper tall men, although it's easier to find them in a crowd, gents around 5'10" are perfect, as being 5'5" I can wear flats or heels and not feel dwarfed nor Amazonian on a date. I go with stacked, rolling accentuates the leg making it look shorter. I'd go with a great belt to draw attention to the waist instead.

[@40OverFashion]

Thanks Rhea! Great feedback, thank you as always!

[@jesselawson224]

I have a pair of dark olive suede captains and a pair of tobacco president boots from Thursday! I love them! And with fall fast approaching(which I’m so glad) I’m looking to get another pair maybe a pair of the black wing tip boots or the new style boot, which kinda reminds me of a desert boot with 5 eyelets.

[@40OverFashion]

Awesome! Thanks!

[@Thursdayboots]

Sweet! So glad to hear that you're enjoying your boots :) Please don't hesitate to reach out to us if you have any questions before your next purchase!

[@caughtonlense6970]

Great to see you to from Kenya bought some boots yesterday...great piece of advice💪

[@ttop64]

Great video John . Glad to see you have joined the chelsea boot band wagon. I love the black and brown pair that I have. I will be wearing them more often now that fall is on its way.

[@40OverFashion]

Yes, they're great! Thank you!

[@jbird761]

I like the convenience of the Chelsea don’t know if I can do it

[@rajkrish9347]

Great video John. Am in my mid 40s (and a 6 footer). Couple of my chinos shrunk a bit in length and was thinking of giving them away. After seeing your video, i garnered enough strength to pair those chinos with boots - chelsea and chukka with almost no break, works a charm. Thx again. Raj.

[@40OverFashion]

Perfect! Thanks!

[@pedrocruz4828]

Just picked up my first pair

[@fastleopard1]

Love their boots. Have 2 pairs

[@40OverFashion]

Thanks Steve! I'm a fan too.

[@BotchedInvestigation]

Stacking looks better with Western/ Cowboy boots. I know I'm late here but have tried Chelseas Heritage to Western Cowboy boots from TBC. Love this video too!

[@EchoSigma6]

Those boots on the Thursdayboot.com’s website are nice, I think the model is The Duke. I really appreciate these videos because my time is so limited, I can get a relevant fashion tip in 5 minutes and determine if the look will work for me. Most of us guys past 40 years of age work many hours, have families, and all the household demands to deal with. Watch, buy, wear, and fashion on.

[@40OverFashion]

Thanks for watching James!

[@wadebolderman3250]

I have many pairs of boots that I’ve owned for years. Two pair of classic Kenneth Cole lace ups in lighter tan suede cap toe and brown leather as well. These go with just about everything. I’m a stack guy as opposed to the roll method, that being said, I will on occasion do a subtle, or very slight single roll on the cuffs of my jeans, being taller at 6 ft 2 inches.

[@bernardtan1]

Just wore my brown leather Chelsea boot today, I like it because it's a "slip-on" for days when I'm lazy on tieing shoelaces or just in a hurry. Chelsea boots makes you walk in a certain way different from all your other shoes. 😁

[@40OverFashion]

Thanks Bernard! I'm looking forward to wearing these a lot more this Fall!

[@bernardtan1]

@@40OverFashion You will notice you would walk differently in Chelsea boots than your other shoes.

[@rayg6584]

Great video John I just purchased Chelsea boots from Thursday Boot Company 💯👍🏼✅

[@yashgupta1620]

I wish thursdays had their outlet in India!They make the sickest boots(judging by the looks).

[@peterdeveau7867]

Boots are the best. Have worn them for years. Just bought a pair of Samuel Hubbard Chelsea’s. Wear R Williams too. No breaks for me.

[@40OverFashion]

Thanks for commenting Peter!

[@johnfarel3152]

Those chukkas look amazing

[@porfirio9735]

Those boots look spectacular on you!

[@40OverFashion]

Thank you!

[@orlandodelacruz5911]

Nice video John. Very helpful. Thank you and God bless you always.

[@40OverFashion]

Thank you very much!

[@alanlawson00007]

Thanks for posting! Always look forward to your latest video.

[@40OverFashion]

Thanks for watching!

[@sisleymichael]

John, I am not rolling my pant legs. I live in Texas. I do not want folks thinking I am a hipster nor am I seeking an ass whipping. Like the channel, just out on this one dog.

[@zacharybohlman4069]

No one cares. Stop caring so much what people think and no one is going to fight you over your pants. Grow up.

[@richardwright4456]

Hi John. Have you ever heard of golden fox boots? What do you think about the quality and price?

[@nottsforest69]

No break look is my fave for showing off the different types of boots. I think the dark wash skinny jean with the black Chelsea boot looks great in that look. Have to think about getting a pair in the future. Incidentally, bought my first pair of raw denim jeans this summer for the roll up look. I found out that caramel colored work books like the Thursday President boots worked really well. I just couldn’t get away with a black boot matched with that jean.

[@40OverFashion]

Thanks for your comment Andrew!

[@eyeheartsushi2212]

Cuffing jeans is not my thing. I’m glad you offered that look in the video 👍🏽

[@40OverFashion]

Thank you!

[@joebloggs619]

Eye Heart Sushi Oh, I would give cuffed pants a miss if 8ou're a big man because it's the same problem as hot big women in slacks. The cuffs make you look even bigger still.OK on small or taller slim men, though.If a big man/woman can create just one plain line from top tyoe, all in same colour,concluding Sox and shoes, with no contrasting belts, trouser cuffs, coloured shoes, unnecessary detail, like cuffs, pockets, pleats etc, they xill look taller and slimmer. Especially if they stick to a plain, darker colour fabric, no patterns or texture and a cool colour eg blue, which slims you. Sounds so boring, I know .Add fun and interest we ith a fancy tie or at the top part of your shirt, near your face, unless you also have a very fat face with double chin etc, in which case, just stick to plain colour, to avoid drawing attention to whatever you want to try and play down.

[@ronm6585]

Thanks John.

[@40OverFashion]

Thank you for watching Ron!

[@aNaturalist]

No break is my fave, but stacking is done with western attire in order to be able to sit in a saddle on a horse and not be wearing "high waters". I keep 1 pair of Wranglers, at the least, to still be in touch with who I used to be.

[@evaldorank7375]

Hey John. I have tô say I have always been in doubt about how to wear boots and what kinds of boots to wear with chinos or jeans. Thanks a lot for your tips! Your channel is forever a must!

[@40OverFashion]

Thank you very much!

[@weswolever7477]

I’m going to take a wild guess and.....the right boot on your right foot and the left boot on your left foot?

[@davidcoleman2796]

I have a pair of Thursdays caption that I love but they can have QC issues. Just really check them when you get them . Mine had a few small issues.

[@joseortega9519]

John, nice video man. I treated myself to some Thursday Captains in brandy color last fall. Cool boots, very comfortable. Have received some compliments from the ladies. Like your content very much.

[@40OverFashion]

Thank you Jose!

[@joebloggs619]

Chelsea Boots look the best.

[@ronniemack4831]

Great video John. I own a pair of Thursday boots, will be buying more. When wearing jeans I always cuff them because I'm short and my pant legs are long. I do prefer the clean stacking look because it makes me look more rugged. Im an old O.G.

[@40OverFashion]

Perfect! Thanks for your comment!

[@albertmanuel5028]

Great video. I wear boots daily and have a pretty good collection going. I have a couple of pairs of Thursday’s in there. For $199 they are a solid boot, but they can not compare to my other higher-priced boots. They need to stop claiming to be better quality than boots like Redwing.

[@40OverFashion]

Thanks for watching!

[@renato_camara]

I lovely your channel !! Brazilian here.

[@40OverFashion]

Thank you!

[@varunpanday2494]

Thanks John !! Much needed

[@40OverFashion]

Thank you very much!

[@davidalonzo1030]

You inspire me to get some boots. I had some Kenneth Cole alligator boots around 2000. They are 21 years old and outdated. Anyway, thanks.

[@nightshade9977]

I usually buy Jeans that properly fit which keeps me from having to roll them up like the kids do today.

[@juanpatricio9204]

Thanks John! I've been eyeing Chelsea boots and you just helped me. I'm a little nervous about Thursdays...have an issue with a pair of captain boots not fitting right. Again, thanks!

[@40OverFashion]

Thanks Juan! This is my first pair of Chelsea's. I'm not sure why I waited so long!

[@albertmanuel5028]

Check out Taylor Stitch. The price may be higher, but the quality is way better than Thursday.

[@Thursdayboots]

Hey Juan! I'm sorry to hear that you're having trouble with the fit. If you reach out to us directly at [e-mail] with more information we'll be glad to see how we can help!

[@sazzadkhandakarcpa9371]

Try RMW boots from Australia

[@CameronEggertz]

Have you ever tested Taft boots?

[@40OverFashion]

No, I haven’t, but I would like to.

[@garthdavies7158]

Thanks John , Great advice especially for me as I am not really a big boot wearer but they are handy for the late Autumn/Fall and Winter Months. I have noticed the younger guys wear the differently by having a small gap between the boot top and trouser leg bottom. This looks strange to me but I like all the ways you have shown in your video and gives me he confidence knowing I will be wearing them correctly .Thanks

[@Hund109]

⁰

[@Rza5675]

Thursday boots sponsors everyone talking boots. Nice

[@ricardofeher5692]

Woow, Nice boots, John ! for me it looks much better not turning the pants.

[@40OverFashion]

Thanks Ricardo! I appreciate the comment!

[@Rualnys]

Great video as always. I prefer the no-brake option bc I have short legs and a bit of extra weight around the midsection. I definitely don't want to appear any shorter by rolling the pants up too much. For my first pair of Chelsea boots, should I go with black or brown? Thx in advance and I enjoyed this one a lot.

[@bernardtan1]

Brown for 1st pair but it also depends on your existing wardrobe color palette. Black makes things go formal while brown is casual. Next question is whether get a Suede or Leather. 💡

[@Rualnys]

@@bernardtan1 Based on your comment I think brown/tan is the way to go. My wardrobe is in its baby stages right now and I hardly do formal. Suede is even more casual than leather so I'm gonna go with the latter. Thx for the tip.

[@rheamorales1329]

Ron, I read years ago to match boot color to your hair color. I have three pairs of brown boots and they accessorize my hair. I vote black boots for you!😉

[@Rualnys]

@@rheamorales1329 Interesting! Some out-of-the-box thinking there. I like it. 😅 @40OverFashion, John you have to get some white boots to match your hair. 😜

[@40OverFashion]

Thanks Ron! I'm with Bernard and think brown would be a little more versatile.

[@Bharat005]

Great video and really nice boots...

[@40OverFashion]

Thank you!

[@MikiBlue]

I am from Australia and I ordered Americans size 12. It was too small. I sent back to Thursday boots and paid $67.00 for Australia Post delivery. So don’t go by Thursday Boots sizing advice. I think I should have ordered size 13 Anyway when I received the boots size 12, they looked nice. I really liked them. But I am no longer game enough to order 13. Just in case I’ll have to pay another $67.00 for return to America. There’s got to be away for company to be more precise with their sizing. I do love the boots that I don’t have.

[@trevellethibou9731]

What a coincidence John I just got some Chelsea boots and I've only worn then with chinos. I fold my jeans so no I have some ideas on how to wear my boots with them.

[@40OverFashion]

Perfect! Thanks for commenting!

[@laurenthanser]

Try Brown Chelsea boots with dark slim denim. Classic !

[@40OverFashion]

Yes indeed!

[@laurenthanser]

@@40OverFashion i live in the Netherlands, a month ago I was in Seattle, and Vegas. I did not see many fashionable guys out there. Guess Europe is different that way. Any idea why ?

[@trevorkelleher]

Great post as usual, keep up the good work.

[@40OverFashion]

Thanks Trevor!

[@ValFinale]

how big of a leg opening would you suggest? 14"? 15"?

[@eh3535]

Awesome vid, good Jean/chinos that have that great taper?

[@gerardw7479]

What about cowboy boots? Nothing fancy , just a nice tan or brown round toe boot. Thoughts?

[@jimklemens5018]

Are you a cowboy?

[@timberhills1778]

Nice video,I have those brown suede chucka nice boots

[@40OverFashion]

Thank you!

[@gdgeorge]

Love the boots you’ve mentioned. I plan on getting a pair. What kind of socks do you wear with boots. I’ve still seen the no sock look but wanted your opinion. Thanks.

[@40OverFashion]

Thanks Gary! I wear full socks with boots. I don't want any ankle bone rubbing.

[@donsmith6254]

Great vid as always bro!!👌🏽

[@40OverFashion]

Thank you Don!

[@CooLT0531]

Great vid, John! What's your opinion on tucking jeans into boots? I have two pairs of boots that have a more rugged, combat boot kind of design, and I have been wondering about my options since I got them. Have a great day, good sir!

[@40OverFashion]

I'm not a fan of tucking jeans into boots. In my opinion, it just looks a little off. Maybe in a year it'll be all the rage and I'll be eating my words. :)

[@CooLT0531]

Thanks for the reply! I'll try them once in a while when I feel like it, but I'll stick to your tips then :)

[@ttop64]

Probably the best way to pull off the tucked in look is with a nice pair of western boots with an intricately stitched design on the shaft of the same or different contrasting color of the vamp. I have a pair of Olathe boots that I have worn with jeans tucked in periodically.

[@bikerider.56]

Don't do it. 😨

[@CooLT0531]

Lol I'm not that crazy

[@michaelalexander8631]

I prefer the traditional no break option best . Rolling up your pants just looks like your compensating for a pair that is too long. Of course, this from a guy who loved wearing high waisted wide leg jeans and polyester pants.

[@martinmugwe923]

Couldn't agree more with your POV! Rolling up looks kinda inelegant too!

[@40OverFashion]

Thanks Michael! I agree, it's not for everyone! :)

[@rickflippin1]

Michael Alexander I concur the roll up look reminds me of Larry Mondelo in Leave it to Beaver lol

[@Gagan99-y2j]

Yes rolling up looks cheap and inelegant.

[@bheinatz1]

John, what width do you you normally have your tailor taper the cuffs to?

[@stephenrobertson7657]

Love your channel John

[@40OverFashion]

Thank you Stephen!

[@carloshernanninich2663]

😀😀😀🙏 texto castellano 🙏mi nombre es Hernan Ninich desde Argentina!!! Tengo 54 años, FELICITACIONES!!! EXCELENTE!!!

[@40OverFashion]

Gracias! Thank you!

[@andrew1212w]

I’ve been wearing Chelsea Boots for years my latest pair are Geox made In Italy and I wear them in winter with tapered jeans turned up one cuff.

[@40OverFashion]

Perfect Andrew! Thanks for watching!

[@kieljacinto3509]

can i fold the denim nor chinos with my jodphur boots? when you wear your chelsea.

[@HorrorFun23]

Did you sell them already?

[@smigglesmiggles614]

How did the cognac suede scouts hold up? Specifically the creasing?

[@keithosorio8598]

I love wearing boots. The no break or slight stack is my go to. I have tried the roll and just don’t love it. It could be that I’m just not used to it? Anyway, I’ll try it again this fall.

[@40OverFashion]

Thanks Keith! It's totally ok, it's not for everyone! :)

[@vinhtran347]

I like the video very much. Because I wear boots (or high top sneakers) all the time. Low tops are not for my feet. However, you mention the no break in the video. But what you show is more like half break or full break. No break means the pants fall right on top of the boots. Or just slightly touch.

[@40OverFashion]

Thanks Vinh!

[@jamesherrera7995]

Prefer the the no cuff look also, looks cleaner, my taste, but like the look on others. Have several pairs of different style boots and really enjoy wearing them.

[@40OverFashion]

Thanks James!

[@YakubibnEsau]

These are great ideas, but if I tried these, I would have the feeling the boots are wearing me. I just bought a pair of Thursday's Vanguards, and they are nice boots!

[@40OverFashion]

Thanks for your comment Guy!

[@monsieurmike2072]

New subby baby!😎👊✌

[@40OverFashion]

Thank you!

[@monsieurmike2072]

@@40OverFashion 🙏

[@marlon9683]

Are the boots in the video black ??

[@dongrainer6405]

Been watching several of your videos. As a boot lover kind of guy I enjoyed this video very much. In the colder, wetter weather here in the PNW boots are a must if you are outdoors a lot. I enjoy walking for my exercise so I do pair my boots and skinny fit jeans for the occasion and I do cuff them since the jeans are a bit long and just look better that way. Besides it gives me a chance to show off my "macho" style boots. They are designed after a military style boot so they are aggressive looking. I definitely have to find a more refined boot to go with my chinos though. Thanks for the video.

[@TheWeardale1]

I've got skinny legs - what fashion tips for trousers etc can you advise?

[@40OverFashion]

I have small'ish legs too. Go for slim fit anything, but avoid "skinny" fit.

[@william719]

I'm way over 40 :( but hey I always enjoy your tips. Thanks for sharing John.

[@40OverFashion]

Thank you!

[@GKHGKH]

Good tips 👍!

[@40OverFashion]

Thank you!

[@brahda808]

Finally, I was waiting for some one to talk about boots and chinos. Wish you would have shown the entire outfit in your video instead of just the boot and bottom portion of the pants. It was hard to see if you looked taller or shorter with certain boots and pant cuffs.

[@40OverFashion]

Thanks for the feedback!

[@theregoesmarc]

Very timely video with fall coming up! I love my chelsea boots and look forward to wearing them this fall season. I wear work boots and Jeans at work. It's in a retail situation so I'm in the public eye a lot and always make sure my jeans look great. Great advice on the tapered look and roll or cuff them up a little. Will have to try some of your other suggestions! Thanks, John for the encouragement and great advice! Cheers!

[@40OverFashion]

Thank you for your comment Marc!

[@toshicasinillo1490]

I haven’t try wearing boots 🥾 shoes but gonna try for sure 🤞🤞🤞

[@erikk.5202]

Thank you for a very informative video. I am not a fan of rolling up my jeans and fortunately my jeans and chinos have a nice slim taper so they show off the boots just right. Like you said though, rolling up the jeans is not for everyone.

[@40OverFashion]

Thanks Erik!

[@brenttesterman1198]

OUT FRIKIN' STANDING!!! I'm bummed I wasn't able to make the meet-up at the winery. Peace

[@40OverFashion]

Thank you Brent! We'll do another meetup soon!

[@robertwong7452]

John I love these boots...I'm just 165cm so I prefer to wear 2 or 3 inches high shoes with laces....haha....

[@40OverFashion]

They're great boots, Thanks!

[@flightattendant82]

John, just like you I'm not a stacking fan! Great video...

[@40OverFashion]

Thank you Thomas!

[@jayare2147]

Another great tip. I think you should do some type of contest where you style a couple of your fans/followers from head to toe. And because I suggested it I feel I should automatically by default be one of them ;)

[@40OverFashion]

Haha! Great idea JR!

[@jayare2147]

You see it’s perfect. You get sponsors for the clothes/shoes/products etc. you can make it a series if you wanted. The possibility is endless my friend!

[@douglasyong6939]

Slight stacking for me, as no break seem to result in the rear catching on the edge of the Chelsea Boots..just my experience

[@40OverFashion]

Thanks Doug! Great point!

[@maxbokol]

Not a big fan of boots at all more so with folded tapered pants. But, man it sure looks good on you. New subscriber here and I love your channel. Also, got rid of my old clothes and started shopping for new ones all inspired from ideas you've been sharing. Thanks man!!

[@40OverFashion]

Thank you very much!

[@richardc2803]

How should you lace a chukka boot?

[@duanebonini2381]

I keep trying the cuff and it just does not look right on me for some reason. Maybe I’m just to short at 5’7”. I see it a lot especially were I am located right now. Thanks for the tips.

[@40OverFashion]

Thanks Duane!

[@Everydaygentleman]

Chelsea boots 👍🏼

[@40OverFashion]

Yes! My first pair!

[@Everydaygentleman]

@@40OverFashion I would say probably not your last lol

[@dougwilson881]

Do men still wear the Sperry topsider.

[@40OverFashion]

I see boat shoes every so often. I think they’re still a viable option, but there are more options these days.

[@lucky37irish62]

Stacking not a good look and thanks for the look back at the 80's with the pin roll. I have to say wasn't a Chelsea fan either but with the 2 roll on the tapered slim jeans, looks killer going to give them another look. Thanks John

[@40OverFashion]

Thank you Paul!