How to Wear Dress Shoes with Jeans and Rules You Should Follow

[@clydechavez3483]

I used to wear my burgundy and also my black long wing wingtips with levi's when i was in 8th grade and 9th grade back in the late 60s. I have 4 pairs of old school vintage now and still wear them with levi's in my 60s. My love for them has never faded.

[@harlanroeser7546]

I'm older & retired. Usually, wear the same clothes now I've had for years! Don't own any dress shoes anymore. I usually wear golf shirts, so I've signed up to update everything within reason. Thanks, John!

[@tipu3624]

Add pics of the outfits,, which u r talking about.. it will be great

[@nickkambitis5340]

Crockett and Jones whole cut brown Alex shoes looks ace with dark blue jeans. I own a pair, and people always compliment the look.

[@pattgsm]

Nice. I need a derby as well. I think that's a better fit w/ jeans. The oxford brogues works nicely when they are very broken in and aged.

[@ksamave2]

Nice advice but would suggest you show a model wearing the dress besides verbally describing it. Overall a great job..!!

[@kjhkjhlkgjklggkhk]

Yup feels like he ran out of time and just published the video w/o creating examples of the full outfit.

[@AbdulRahmanNoor]

I agree. I'm the kind of person who doesn't know a loafer from a Derby and would've understood what he was saying with an example.

[@ronaldvandyke5711]

Yes agree!

[@brettrusso6703]

I wear my 1920s brown and white wingtip shoes with my jeans and I get a lot of compliments

[@LUribe408]

I believe you should dress how you want too. Most importantly, dress in a way that makes you happy. The mistake people make is, they try to copy someone and deep inside they ain’t happy.

[@MeepMeep88]

Yep, wear it and own it. Walk with confidence and everything will match. Lol hell I wear a fkn gray belt and brown shoes.. If anyone gives me shit and say my belt is SUPPOSE to match my shoes I'm prepared to say "Fck off, it's casual wear. It's not SUPPOSE to match.." Lol it's a cool gray metallic-y gray belt. Pretty much matches everything though, I like it. And screw buying gray shoes just to match my belt LOL.

[@frankrosario2120]

I kind of agree with breaking all the rules to dress how one cares to. The issue is that by dressing this way one can look so discombobulated and disheveled that it's not only embarrassing to ones self but can also make all other men seem like we dont have a clue as to how to dress at all. Good luck on this one .

[@frankrosario2120]

@@MeepMeep88 confidence can make one look most assured but not necessarily well put together.

[@Transformers147]

but most desirable thing is everyone wants to be favorites of everyone.... it's force you to make different of get in copy of original

[@Heywoodthepeckerwood]

Yeah.. dress like a child your entire life. Take care of your home the same way…

[@ZoomZoom-ng6sn]

I do wear these light blue Levi's 511s with a light tan dress/casual shoe. Doesn't look bad. I use it for hot summer days.

[@bjdough8916]

These are some great shoe styles. I have 2 pairs of oxfords. Both are by Cole Hanan and one is more polished. I reserve these to wear with khaki pants, long sleeved oxford shirt, and a sweater when the temperature actually goes below 65 degrees or on Thanksgiving and Christmas with the family. The other ones I wear with jeans or khakis.

[@WheelieMacBin]

I find ankle length desert boots work well with lighter shade jeans too. I really enjoy your style tips, cracking stuff.

[@TommyAlanRaines]

Something I noticed you may want to do a video and an article on is Inseam ; I say this because many guys do not know the difference between true inseam and tailored inseam. True is were the total length starts from back side of the package to the bottom of your feet flat on the floor; then Tailored is were the bottom hem is roughly 1 inch below the ankle. Denim with True Inseam works with Athletic shoes, Cowboy Boots/Western/Roper and some other pants like cargo and Tailored Inseam Denim Dress/Semi-Dress Shoes.. So if you true inseam is 32 then you want a 30 for that non puddled look with dress/semi-dress shoes.

[@fabergefolliesdancentumble3023]

I'm a girl and I love listening to your logic. It's universal.

[@michaelplantus2261]

Brown Oxford or Chukka goes well with dark wash jeans. They are a nice casual look that should remain in style Imo. Very popular so I see why this video is such appreciated. Keep up the great reviews! Thanks.

[@joydharan3860]

Will strictly follow your videos. Very guiding..thank you!

[@christianwolfe4405]

Great advice , it feels good when i dress up. most guys dress the same . i like to stand out , get the attention of the pretty ladies. it is a passion of mine. keep it up i enjoy it.

[@samhancock3585]

Please start showing more combo's, such as different styles of jeans with different shoes accommodated by stylish belts and shirts. It would be greatly appreciated. Your style is spot on and we enjoy your unique tips. Thanks in advance.

[@joydharan3860]

Hi John! you are awesome! I recently started watching your videos. Liked it as I am 57 years old...

[@40OverFashion]

Thank you!

[@ifran77]

Starting to like your vids more and more, you seem genuine and give good advice...keep up the good work 👍🏽

[@40OverFashion]

Thank you very much! 😃

[@FashionNick]

Amazing video John👌👌

[@q-storm767]

Blessings 🙏 to 40 over Fashion. I have a pair of Black demin jeans and I wear Brown Rockport Oxfords with them.

[@deannoble673]

This might be the most important subject for the guys this channel is aimed at. We all love our jeans but can we say that we do see a few guys not get this one quite right. All the shoe choices here are absolutely spot on by the way. All I would add is that getting the jeans right is key. Personally I’m happy to spring a bit more for a top notch pair of dark wash selvedge denim. Some might blanch at paying more but in my opinion it’s the best investment you can ever make for your wardrobe. They are so versatile look fantastic last forever and actually get better with age. What’s not to like about that? Worth finding a boutique store where whoever is attending you can help make sure you nail that all important fit. Excellent stuff John.

[@40OverFashion]

Thank you very much Dean! Always appreciate your comments!

[@lukecage9836]

Happy I found this channel. I have the Allen Edmonds Strand too!

[@donschenck2466]

And now I know the difference between an Oxford and a Derby! Thanks!

[@Kevin_Phu]

My daily wear is slim black jeans with a pair of brown leather cap toe boots. Very clean and casual look. It's usually with a polo or casual button up shirt. I don't tuck my shirts in for a more casual look and they aren't long either where they look sloppy.

[@gilbertb8078]

I'm learning,I'm learning.You teaching this Caveman how to dress.Thank you.I love your posting. I am a Fan,now.

[@C-4U]

Came upon your vid quite randomly, stayed and watched. Glad I did, great styling advice and tips. I've been ultra casual for too long and I'll be coming back for more of your styling guidance as I get to grips with updating my look to a smarter, sharper 65 year old. Excellent videos, thanks for posting 👍🏻👏

[@40OverFashion]

Thanks for watching Carlo!

[@C-4U]

@@40OverFashion My pleasure John, plus you're very easy on the eye to watch and listen to. A bonus..👍🏻

[@q-storm767]

Since I purchased a couple pair of brown oxfords, I'm looking forward to sporting them with demin.

[@terrysigstad8252]

For those who think shoes don’t matter, you are mistaken. Women definitely notice your shoes. I have gotten many compliments about my shoes. It’s not that they are expensive, it was because they were shined and not worn out. Wearing a suit with beat up shoes destroys the look you are trying to achieve.

[@TheGilbalfas]

I want to go out with my best jeans and brown boots now. Thankyou!

[@FJE304]

Clear as day, very insightful. Thanks for helping me, a 40 y/o working pro, get a handle on gentlemen style.

[@Latinart]

This video on how to wear your denim pants the right length to showcase the shoes, Is right on point. I’m taking all my denim to my tailor ASAP.

[@horatiosvengali4624]

Latin Tart that’s the hardest part for me especially with my size 14 and no-show socks...

[@Latinart]

Horatio Svengali If your over six feet tall then I think it’s normal to have a size 14 or lager foot. I’m short at 5’6”ft my size foot is a 10- 10.5in a large to average size for my height. But I still want showcase my Italian leather shoes.

[@juanarce6900]

Gorgeous oxfords John. I lack oxfords, and derbys in my shoe collection. I must acquire both types to elevate my style.

[@OWOT-re5jf]

Like the cap toes and monk straps.

[@williamkazak469]

I wear jeans occasionally, with a crease. I seem to prefer kaki's with a crease mostly. Sperry makes quite a variety of canvas and leather shoes suitable for both kaki's, jeans or shorts, not just their traditional leather boat shoes. My leather shoes are from Church's Shoes. I have a variety over the years including a pair of their white buck wing tips. I purchased a white buck derby type shoe this year after learning about Ivy Style. Shoes can be quite interesting. I don't know what women like but they are not staring at my shoes, especially during conversation! I had to get that remark in somewhere! I have heard it said too often.

[@KenoshaGuy72]

I haven’t owned any brown shoes for years or any classic dress shoes re any shoes with a leather sole and a rubber heel. I wear mostly driving shoes, most all of my shoes are Prada ( I can’t help myself) with a few pairs of Vans thrown in and always one pair of sneakers for exercise only. Also, I’ve been doing this look for 40 years when all of my other friends were out wearing their latest trainers out at clubs I’d be sporting a pair of Walter Steiger or Vittorio Rico or Mario Valentino‼️ nice to be validated!

[@davidnorman4923]

Great advice thanks! Picked up a pair of light tan derby type shoes to pair with dark levis and a lilac tailored shirt hopefully that is correct!

[@uncleyang8697]

Follow your advice, bought Slim Denim and brow Derby yesterday

[@donschmidt2537]

I really prefer black loafers with my jeans, with a black belt. The jean type, dress shirt and sport coat advice is spot on. I always throw on a blue blazer. I do have to say, i experimented with a pair of black patent leather shoes from a military surplus store for some years, and people liked them. They were actually comfortable. They fell apart and i never gor a second pair.

[@jimkaufman214]

Yes, I am with you. I always wear black shoes and belt but based on the video, I will try to do more brown :-)

[@henry222ist]

@@jimkaufman214 I like the black look at well, try to avoid the shine black ones for a less formal look imo

[@bernardhollis7834]

What about Chelsea boots? They are quite popular here in Australia.

[@DavidSaintloth]

Actually, SOME people can pull off a whole cut with jeans IF one also accompanies the ensemble by: dress shirt , tucked IN. Blazer with pocket square , conducive to ensemble. Jeans that are fine weave, (looks almost like dress pants from far away). I'm in the pedantic weeds of fashion minutia here but ...there it is.

[@ramaarbaird4137]

Allen edmonds double monk strap shoes all day with Jean's. Killer look.

[@40OverFashion]

Yes!

[@michaelremer7721]

I learned so much from this video

[@dr.abhishekpanday6274]

I really like double monk

[@davidh8478]

I'm 38 but still subscribing!

[@larryfalkin63]

I mostly wear black jeans, Levi’s 511 so black shoes go really well with them. A navy polo with a light blue collar and I look dressed up while still being casual. Put on a dark blazer and you can even go out to a nice restaurant and not look overdressed.

[@tnetroP]

I agree that brown is more versatile than black. But I'd have to go with a derby when wearing jeans. It's less formal and so goes better with less formal trousers. Derby brogues with non-distressed jeans and a white OCBD look fantastic.

[@searchrankoptimize]

It would help if you name the brands which ship internationally. The generic shoe name are good. But specific brands will help as well. Because not all brands make all types of shoes. You could also be more specific and give advice to folks with different budget ranges: High End, Mid Range, Low Range and Pocket Friendly (the fast fashion types which are the easy come easy go and since price is low, its the way-to-go for many). Not everyone would like to straight away throw big bucks on expensive shoes! Some (lets be honest) cannot even afford them! While this channel is for a specific demographics, certain demographic groups may want some affordable fashion suggestion! Important: Please do recommend something for those in South East Asia viz Indian Subcontinent, Nepal, Thailand, Singapore, Malaysia, Indonesia, Ceylon, Vietnam, Bangladesh, etc. This should be super helpful. Finally, good going! Keep it up!

[@mickeydesouza908]

Hi 👋 John thanks from trinidad

[@leslielee7670]

Would like to have seen more visual pix, along with your comments.

[@ttop64]

You mention wearing dress shoes with dark wash jeans. What are your thoughts on pairing dress shoes with colored jeans? I quite frequently wear my walnut Strands with a pair of olive green or khaki colored jeans and I have a pair of black cap toe oxfords that I will wear with a pair of dark gray or burgundy jeans. I always value your opinion. Thanks.

[@40OverFashion]

Yes, absolutely! Those pairings sound great!

[@PaulEllisBIGDATA]

Next time please wear the outfits and shoes so we can visualize the style pattern. Appreciate your video. Please keep them coming.

[@40OverFashion]

Hi Paul, thanks for your comment! You're absolutely right. Next time for sure!

[@DirtyCruze.]

Perfect hair bro. Your videos helped me dress way better than what I thought looked good in.

[@c.1211]

Finally! A real alpha that knows what his talking about.👍✌😃

[@40OverFashion]

c p Ha! Thank you very much my friend!

[@tr78478]

Please! You know the whole "alpha" thing is a bunch of malarkey (or is it malarky), right? Are you friends with this guy? Wait....is this Jordan Peterson?

[@stephanx2384]

Great video as always, however I think Oxfords, no matter if worn with Jeans or not, require straight lacing (or parallel lacing), not criss cross lacing as shown on the pair in your video.

[@40OverFashion]

Thanks Stephan, I made a video after this on straight bar lacing. 😃

[@chetanhmeshram]

Thank you for saying the pulling off part

[@vashkardhar803]

Thank you for your idea

[@mememooree]

New follower... Great public service for EVERYone. Wrt to dress shoes color, where do fall on blue dress shoes?

[@ramnathrambisoon2134]

Nice dress shoes I love it but I like slip on

[@justinchipman1925]

As a former carpenter and home builder, I need to upgrade my look to the role that I have now. While I wasn't a candidate for a show like What not to Wear, I definitely need some of these pointers. Thanks.

[@lifestyleniall]

That first brown shoe looks like Allen Edmonds Strand Cap-Toe Oxford, what color is it please? Cigar? Walnut? Thanks!

[@duanebonini2381]

Any recommendations for a shoe with black denim ?

[@40OverFashion]

Black boots are killer with black denim.

[@65Davis65]

Good advice, thanks, Davis.

[@40OverFashion]

Thank you!

[@user-pz4tx7if9d]

I think oxfords are also ok, if they’re not too dark brown. And you can also use the brown dress shoe in suits, because they are oxfords. I think that brown Oxford are very versetaile, but I have heard much against my opinion. But German classic fashion from 20s-50s is very different to western/American one

[@kevinl6231]

Be daring and wear walnut colored shoes with black jeans and black jacket; or even a fashionable but not formal black suit. Don’t forget to match the belt. It works!

[@aspensplace3293]

Good. More visuals would be helpful.

[@jaihindletsdieinthethickof4219]

Too good a tip.... Fashion at its best.... Footwear indeed a signature is a Men's fashion. Classic presentation brother... What about the waist belt and bracelet..... Please do some when u can... I will be waiting budds.... Cheers

[@ianmedium]

I have a pair of burgundy Church’s Shannon shoes which have a double oak tanned leather sole, they are one of the most versatile pairs of shoes I own and they go fantastically with jeans. My first visit to your channel, subscribed!

[@RMD147]

I have different colors of brown, black, blue, red, green, bordeaux and they al work with jeans. the only think you have to wacth color of the jeans

[@davidrincon5556]

If u have spitshine shoes it separate s you from the rest boom like that n always match your belt n shoe color

[@JosephSmith72]

I do this all the time. I wear my Johnson Murphy's with dark tapered jeans but I don't always tuck my shirt in as in a previous video John showed us how to look when wearing the shirts out. Has to be the right kind of shirt. Good video John (again) Keep up the good work man!

[@40OverFashion]

Thank you very much!

[@aashaikh3463]

Thanks for sharing I do like your videos and your dressing style appreciated !!

[@Recon6]

John nice to meet you. I just joined I am going to ring the bell. I am 60 like to dress nice and began when 80s Miami Vice came out 👍

[@40OverFashion]

Thank you!

[@1.masterpiece]

What colour should the belt be? Should it be matching the colour of the shoe?

[@tonnyjohan640]

Thanks for this informative vid. Regards from Jakarta

[@rajabidisaid3934]

great advice jeans and dress shoes to wear with

[@ivancapuz9471]

I always wear polo shirts and dark slim jeans. What kind of shoe would i wear? Tnx.

[@ChiefSmokeAlot]

Turned 30 two months ago, stumbling upon this video and channel today. Subbed! I like your style and tips sir.

[@40OverFashion]

Awesome! Thank you!

[@newold9079]

I LOVE YOUR SHIRT WHAT BRAND IS IT?

[@artorius5414]

that monkstrap and jeans really good

[@jbinpo]

Great info but more visual aid would be better.

[@anumanconsultant3941]

good video. just as you explaned about the bottom of a jean the hip also is imortant for a perfect fit. As you grow the butt is the firt part of yout boduy which will start loosing its mass and will start limping down gradually. so that also needs to be considered. everyone does not have bulky body but they really carry gracefully.

[@fasteddyri]

John what’s your opinion on 60 and over. I’m a well dressed man for my age. I’ve listened to most of your videos and I take your advice from a man over 64

[@afrieser]

Great tips! New follower from Chile, cheers!

[@vince-qb6su]

Nice video. Do you always match the belt color with the shoes color?

[@jimkaufman214]

Yes, I always have a matching belt. I lean toward blacks which makes the belt and easy match. Browns are tougher to get the exact color match but is awesome when they match perfectly.

[@vince-qb6su]

@@jimkaufman214 Great. Thanks!!!

[@lesradfordjr4761]

What do you think of the classic Chuck Taylor white hightop

[@thomasmargolis3313]

what makes you the 'expert'? The producer Michael videos have their, not sure what that is though. Sporadic is good enough for me there. He's rich enough to be eccentric, and happy to be so w/o your input.

[@mlee9049]

John, based on fit; do you have a favorite brand of jeans? Do you usually prefer to roll up the bottom of your jeans? Thx.

[@juanjosefermin3682]

I will always prefer double monks as opposed to single. Both you own are killer bro!

[@40OverFashion]

Thank you!

[@FARID1870]

Same here. Single monk buckles tend to be huge. Double monk buckles look more discreet. But it is all abt preference 😊

[@rennedelorean3341]

@@40OverFashion I prefere the single buckle, the double buckles are off center and the single buckle is not that big, depends on the 'maker' of the shoe. This design came out in the late 1960's early 1070's, I had two (2) pair back then, I was about 19 or 20 years old. Now 2018, I got one pair (cognac) at Neiman-Marcus, the other pair is a taupe coloured suede, from 'To Boot New York' - Consistant compliments on both pair of shoes, especially the 'cognac' coloured pair from Neimans.

[@VGAPI]

Showing full examples of what you describe as the right combinations will be very helpful. Great video over all. I’ve subscribed and gave like.

[@slisyd]

Can you wear wholecuts with chinos? i love wholecuts they are stunning.

[@walter4717]

If they are brown you could try

[@harrilahti-luopa5953]

I am over 40 too.

[@alvaro7546]

Greetings from Panamá. I need to know if is important wear brown shoes with a belt of the same color?

[@40OverFashion]

Yes, it's somewhat important, especially when dressing formally, that the belt matches the shoes.

[@frankrosario2120]

Hair styles such as his conform to what t.f he thinks is correct. Meaning right length not necessarily how it appeals to all else. Pompadours are not only hard to shape but to maintain as well.

[@horse4848]

Which Pant Colour use of Grey Colour Shirt

[@adarshfaridkhan3361]

Just tell me which product do you use for your hair?

[@Abhisheksharma-oy9zm]

Very nice content, kudos to you

[@achillesavendano5267]

Awesome....thanks

[@shahzaibshakeel8128]

Thank you 💫😇

[@rvrebel2209]

Hi. I very often wear a Loakes Hoskins tan boot. Unfortunately I do not like shoes , I like my ankle joint protected. I am very interested in your views of wearing a Hoskin boot. Please.

[@9353678]

Informative video gr8 job....