How To Style Oversized (Relaxed/Wide Fit) Clothes

From casualwear to tailoring, fashion has definitely gone wider and more relaxed all across the board in recent years. Could it be the end of skinny jeans? Maybe. In today’s video I’ve brought on a special guest, fashion KZbinr Daniel Simmons, to educate us on styling relaxed/oversized clothing. I could not think of a better spokesperson for this topic. A quick glance at his Instagram feed or his KZbin videos is more than enough to realize just how much he has embraced this style, and Daniel clearly knows what he’s doing.
Hope you enjoy the video! Share this with a friend looking to experiment with oversized/relaxed clothing, and make sure to check out Daniel’s channel if you haven’t already!
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Daniel’s KZbin channel: / @imdanielsimmons
Daniel’s Instagram: / imdanielsimmons
My Instagram: / timdessaint
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Music:
Come 2together - Ooyy
Reanimation - Dylan Sitts
Closure - Dylan Sitts
Betterlate - warmkeys.
Throne - [ocean jams]
Dusty Conscience - Matt Large
Hisbiscus - [ocean jams]
Lean - [ocean jams]
Corn Candy - Guustavv
Rustic Endeavor - Guustavv
Music downloaded from Epidemic Sound: share.epidemics...
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Shot with:
- Canon 6D MK II: amzn.to/2COFiyW
- Canon 24-70mm f/4.0 Lens: amzn.to/2RUFctW
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Some of the links above are affiliate links, meaning, at no additional cost to you, I will earn a commission if you click through and make a purchase.

[@FlyWithJohnnyThai]

This was seriously one of the best videos on oversized clothes and mindset for shorter dudes. Great job guys I learned a lot 🖤

[@TimDessaint]

Thank you Johnny! Really appreciate it and glad you enjoyed it! 🙏

[@Tommygimbal]

Make athleisure lookbook please for both of you guys, you guys contents are great!

[@Thefire591]

Short kings rise up

[@Gnurklesquimp]

I'm not short, but I personally think so, SO many of the types of outfits I like look best on short people. Tim himself doesn't look all that short to me, but he's definitely in that range where those various kinds of larger fits I love sit perfectly to my eye. Also, bonus points for tailoring, I think cutting/cuffing things shorter is basically always an option, whereas I've had to cut my losses quite a bit, especially since cropped shapes usually don't suit my style.

[@imdanielsimmons]

Thank you for having me Tim! We still need to finish that video for the other channel ;) ps. Sorry about the chair....

[@TimDessaint]

You definitely owe me a chair.

[@bradleydavis4014]

Have you got a link to the t shirt you’re wearing Daniel? Thanks man!

[@sigh.sy.s]

@@bradleydavis4014 he has a video where he shows all the t shirts he owns pretty sure

[@leetcodeprodigy]

@@bradleydavis4014 it sold out and not coming back cause it was from a previous cos collection

[@Hell0W0rlds4]

I want those boots where did you get those?

[@ElliotJatomiSan]

Find yourself a person who looks at you the way Tim looks at Daniel. But for real, I love the way you look as though you're genuinely listening to what the other person is saying. Great video! Thanks for this collab guys!

[@TimDessaint]

Haha that's because I am genuinely listening and interested! 😊 Glad you enjoyed the video Joanna! Thank you 🙏

[@tolcserygergely]

Find somebody with the same interest, and close to same level of intelligence, and bang!! you're there ;) it's harder than it sounds, btw

[@deletethishow7308]

@@justcallrizq4589 Andrea, u think only gay men listen?

[@tonkotonko]

@@justcallrizq4589 and if....who cares?

[@SoWhosGae]

Bana Carat Yep pretty gay

[@martro_]

“Got a hot date, something like that, your girl calls me up” I freaking lost it lmao 😂

[@TimDessaint]

Same. hahaha

[@KaluArt]

1:45 The story of my life. When i started going to the gym and get bigger i realized how the fashion industry is so concentrated on tall/skinny guys to create aesthetically pleasing fit. Him and Kanye are the inspiration for most of the clothing I wear. Go too slim and you will look like a sausage go too over-sized and you will look like a minecraft character you need to find the sweet spot between the two

[@TimDessaint]

It's all about finding that balance! Daniel definitely figured it out for himself 👌

[@koirasikin]

As a female I have also noticed that fashion isn't created for big butts or boobs (unless u want to highlight those areas and wear gym wear all day) It's all about that sweet spot in between!

[@pikouloklakshamernda3913]

good words my guy. like i'm quite short for a guy and a bit buff. so it's pretty sad on my side.

[@dren5810]

@@pikouloklakshamernda3913 I feel your pain. I'm 5' 7" and a little bulky in the shoulders, thighs, behind, etc. Its so difficult to find clothes that fit well because my torso is shorter too. Its rough out here lol.

[@6ix835]

@@dren5810 for tops consider women's section which are often cut shorter. men's collections are finally moving to more cropped fits thanks in part to the influence of streetwear, japanese brands, etc.

[@Imnathgriff]

Yesss boys, the collab we've been waiting for! Such a great watch! That little intro skit though 😂😂! Great job boys!

[@TimDessaint]

Thanks a lot Nate! 🙏😊

[@grantmowry2195]

Daniel: I like my clothes thiccc

[@lildentifrisse4816]

"Not as good as you thou" "*nah*"

[@Chatz01]

humble king

[@distinctloafer]

@@Chatz01 Maybe he is agreeing " Yes, you are not as good."

[@tolcserygergely]

I've lost 40kg in 2019 so I've got a full wardrobe with oversized clothes :DD

[@tolcserygergely]

And now, I know what to do with them, and I'm not joking :)

[@TimDessaint]

Congrats on the weight loss! 😊

[@tolcserygergely]

@@TimDessaint haha, thank you. For me these "regtime chlothing" things looks similar to oversized fashion, maybe I can stole some ideas from there for my big Santa Claus size shirts :)

[@ayywolf]

Nicsak, egy magyar :D

[@makkaucbkia9640]

What a good problem to have haha

[@antoniovandias8653]

"In the world of real success there is no competition" Great content as always guys. Hug!

[@SaxandRelax]

Tim, if you don’t tell me where you got that mint green sweater... well I won’t do anything, but I will be very unhappy ☹️ Edit: 3/27/21 Tim I’m fucking serious where did you get it

[@animechild26]

He said is from COS in the video. I hope that helps you.

[@sabihbinmasood]

I literally just got into Relaxed and oversized fit and got blessed with this video.It's like you read my mind.

[@TimDessaint]

I got you! 😊

[@sabihbinmasood]

@@TimDessaint just like always 🔥

[@WhyJustWhy-oe9dz]

When you realize that you’ve been wearing oversized your entire life cuz ur parents buy everything 2 sizes too big saying that you’ll “grow into it”

[@mikebrickyboy2875]

I really love how you all are not just basic fashion youtubers and tim your always trying out something new, getting out of your comfort zone and just rocking things dude! Respect! I love it :) i also try out lots of things and actually it is true. People put you in a box just because of the way you look. It's crazy but true i see it everyday and feel it :D

[@TimDessaint]

I appreciate the kind words Mike! Keep on experimenting and not giving a damn what people think! 😊

[@mikebrickyboy2875]

@@TimDessaint i won't stop trying out new things ever. I love to experience new things and try out something new! I'm an artist and a really creative person so... I guess no wonder why i love fashion :D i think fashion is a statement and a lifestyle of yourself. Not just clothing that your not naked outside :D

[@ruguoserliegise2716]

Tim: welcome to my first collab of the year One Dapper Street: Am I joke to you?

[@TimDessaint]

First on my channel! 🙂

[@ruguoserliegise2716]

Tim Dessaint Cheers mate! Love your content as always

[@gregory7958]

I asked you for a collab with Daniel, and you really did it! I'm studying right now, but I'll definitely watch it. Thanks, Tim!

[@TimDessaint]

Yess it's finally here! Hope you enjoy it 😊

[@BastiSebastian]

Best collab ever! I bough a lot of Uniqlo's SS2020 collection because of Daniel's video. And now I learned more on how to style them on this post.

[@iamdarryl]

One of the greatest collab out there in men's fashion. This is genuinely entertaining and informative! Great job guys

[@Usario321]

I love your channel man, been watching your videos for a while, they’re great. But I gotta disagree with you on this one, I don’t really think the “oversized” style looks good at all. Also, when you roll up your pants like I’ve seen in a lot of videos, it’s just not a good look overall. I think the best for pants is the “no break” or “quarter break” cut that you’ve showed in a previous video. But everyone has a different style, that’s just my opinion. Keep it up 👍

[@jialian93]

I think it looks good on some people but I don't think it generally looks good either and I think the trend will die soon.

[@TimDessaint]

And I respect that 🙂 That's the beauty of fashion, we all have different tastes/preferences! What one person might think looks amazing might look completely horrendous to another, and vice versa.

[@Usario321]

Tim Dessaint exactly! I’m glad you answered so I could see your take on this, and I agree with you. I think your channel is great and I think people should keep watching your videos and adapting your ideas with what each one thinks works best for them, I think that’s the best way to go.

[@lyingonabeanbag]

This is him teaching me how to wear my wardrobe. All I've got is oversized clothes

[@ariqkim]

daniel look like a snacc in this video, specially those eyes and eyelashes

[@M4NA5]

Ari Qurniawan Should I call you mista?

[@ariqkim]

MAN45 idk what u mean

[@leonidaspilios1013]

@@M4NA5 why are u gae?

[@retrocute]

Who else digs Tim, Daniel, and Marcel (One Dapper Street)? Very underrated style trio

[@mikebrickyboy2875]

I watch tim and Marcel a lottt daniel i actually haven't known but the trio is reaaaaly underrated cuz they are all trying something new and not just the basics and the safe station and they are all going out of their comfort zone and i love it!

[@retrocute]

True, Daniel for example rocks a tote bag hard, couldn't help but try it myself

[@ddjdz93]

Tim, Daniel, and Devan is the trio for me. Marcel is cool, but a little too proper for my own taste.

[@TimDessaint]

I think you'll want to stay very tuned for my next collab... 😉

[@mikebrickyboy2875]

@@retrocute Tim wears roll/turtle necks alll the time.. Hm i wonder why i got 3 of them now in my wardrobe lmao :D

[@elijahkim4172]

YESSSS. Two of my favorite fashion influencers!! 🎉🥳

[@TimDessaint]

🙏💛

[@MTCMVMT]

Absolutely the perfect person to talk about oversized fits. I’ve been absolutely loving Daniel’s style as of late, and it’s been pushing me to dabble into these type of fits

[@znebrem]

Need more of you guys together! Awesome chemistry. Best collab I've seen. (Can't believe he rocked all those pockets on the pants)

[@TimDessaint]

Definitely will be collaborating more in the future! Glad you enjoyed the vid 😊

[@cathymj15]

Does anyone know any KZbinr women that does this kind of vlogs? I really like watching this kinda vlogs but im having a hard time finding women who does the same type of content.

[@FPSZeb]

5ft6 dont give a fuck im wearing relaxed/oversized clothes i grew up with hand me downs from a step brother much taller/older than me its what im comfortable and i dress for comfort first.

[@SomethingEtc10]

Did he just call 5’11 average? I must be way below average at 5’6 😂

[@kairnning4473]

Great hearing people talk about shopping in different sections. Clothes don't have gender, but people come in all shapes and with different aesthetic preferences. Don't let labels stop you from buying clothes you like/fit your body!

[@TimDessaint]

Yess couldn't have said it any better! 🙌

[@sagardipchoudhury1714]

I am a shorter guy and I always wanted to wear overcoats but idk whats bothering me so much😔😔😔

[@kinkaly]

Confidence is such an important part if this discussion! I'd say I'm the most "experimental' of my friends in terms of men's fashion, and my friends always just go "oh you can pull it off ". I honestly just think it comes down to my buddies just not having the confidence with trying new things..

[@TimDessaint]

100%!

[@MJ-cv7yq]

I'm not really a fan of the oversized fit and I don't think I would be comfortable wearing it but you guys did a great job and it fits you both very well. Another masterful video from you Tim. Keep em coming!

[@TimDessaint]

Thank you very much! Glad you enjoyed the video 😊 And I hear you, gotta stick with what you like best on you!

[@nl294]

I think he would look so much better in slim fit. The personality of both are beautiful and I enjoyed watching.

[@thecaveoawesomeness]

Can you give us some info on the cargo pants and green pants Dan has?

[@TimDessaint]

I'm not sure about the brands, but you could try asking him on Instagram 🙂

[@TheSwedishGuy0202]

how to “experiment” with a hole in my wallet 😂 that’s the main question

[@harshitahuja1205]

A very entertaining and informative video. Haven't tried the oversized trend yet, but i'm definitely going to!

[@mikebrickyboy2875]

I think it's not just a trend it's more of a lifestyle ^^I dev. Like oversized a lotttt

[@TimDessaint]

Glad you enjoyed it! 😊

[@Ja-vg2id]

14:31 My mans Stevie Salle: spotted 😂😂

[@hanhan9487]

if i get the virus .. watching this collab might be the cure man..

[@kurthumphres1685]

SPOILER ALERT: There's no rules

[@coracore135]

You both hit key points on how to wear oversized clothes properly and being more intentional. An amazing collab!

[@TimDessaint]

Thank you very much! Glad you enjoyed it 😊

[@Fausto_moh]

This is perfect timing I wanna experiment with oversized and relaxed fits. Daniel is an inspiration and I loved this callab

[@kateciekura7228]

Hei. I am here like.. in 1:12 and .. do you watch PETER McKINNON... cous if not.. you should watch him. He is amazing, and you are nailing it!! Good intro man!!!

[@TimDessaint]

I do! Peter's awesome 👌

[@johne0824]

Awesome collab! I've been liking oversized hoodies lately and planning to go for a relaxed pants. Will definitely take these advice thanks

[@ajk9708]

I’m 30 , height 5,5 brown guy , skinny only weight 60kg... not sure if it will look good on me , my mind doest all me tho

[@BoBoInnovation]

Oversized or wide fit outfits aren't that friendly to shorter guys. Some shorter gals can pull it off and they can look very cute, though.

[@maxcruz1581]

i've never been a fan of oversized shirts, out of curiosity i bought one, then two more and three more, coz i never knew they were damn comfortable. I am not muscular so back then i have this fear that it will make me look shorter. But i knew i want to wear what i want, what's comfortable for me and not to look taller.

[@ManoloVintage]

This video was very helpful. I'm 5'8" and I'm moving from a slim fit style to incorporating a relaxed fit style. My first step, I am most comfortable with, is moving into a relaxed tapered look. I bought 3 pairs of trousers and went with my size in 'regular' instead of 'short' because it offered a wider pant leg. I'm loving it. It's so cozy and comfortable. Next I want to experiment with various pant lengths but I'm unsure of where the hem should stop exactly.

[@Razielbb1]

Love these videos! You guys inspire me so much with fashion after losing weight, I find my fashion sense changing. Starting university aswell I can’t show up same outfit everyday like in school, so thank you again.

[@TimDessaint]

Yes! So glad to hear that Bilal! Much love!

[@DreamGhostX]

Tim: "Great videos by the way. Gotta go check it out" Daniel: *Laughs* "Not on your level but we're getting there" Tim: "Nah" *Dead*

[@reevosaulus]

Now I subscribed to Daniel's channel as well. He's as good as you, Tim! All the best to both of you!

[@imdanielsimmons]

Welcome to the family!

[@mantsisnick]

And for a short asian guy oversized craplooks ridiculous

[@dddreu]

the problem with oversized shirt for small guys it will make you look more shorter

[@vuchihuy1540]

The vid i had been looking for, thanks Tim 💪💚

[@TimDessaint]

I got you! 😊

[@arnabchakraborty7226]

Please make a video on 90'outfit😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏😏

[@Louislaxamana]

Thinking of changing up my style. And I stumbled upon this video. One question though: I am more of a tall and lean kind of person. Would this oversize thing fit me well? Thank you.

[@TimDessaint]

Of course it can! It's just about finding the right proportions 🙂

[@zac277]

My 2 Favorite fashion youtubers !

[@newrob5334]

exactly. forget what society thinks or says that you should wear. i'm an artist and i'm 56 and my personal fashion aesthetic is clean streetwear mixed with classics. i love the look and i feel like me ;).

[@TimDessaint]

Yes! There for it 🙌

[@v_g_v_]

Ahhh!!! My two favorite men’s fashion KZbinrs!!! My heart is happy ❤️

[@jamespawelek-lacey1778]

What was the name of the brand Daniel said he liked to buy?

[@beurreamoustache3333]

Nah he didn't ruin the flow, that was some drip.

[@arianarubiano8144]

The perfect match!!! I´m a woman who always wears oversized clothes and this is AMAZING and inspiring. Love your work Tim

[@TimDessaint]

Thank you Ariana 🙏💛

[@Phaseish]

I live in Florida and I am so jealous of these fits lol I would wear lol and die in of heat in 2 hours.

[@태이씨]

Id say in 20 mins

[@Phaseish]

@@태이씨 20 seconds right now with all this rain .

[@SaiasG]

STEVIE SALLE COLLAB

[@teungkualwansyah6678]

Hay, i am from Indonesian

[@Checkernap]

Loved the collab bro i could listen to you guys all day. I‘d Love to see a Podcast every week from you both

[@hisurf1761]

Ha ha that was unexpected. The moment i saw that tatooed arm i knew this video gonna be hella lit

[@jeremypradipta1405]

how much is your tall? i need for the ratio

[@LorenzoGapud]

It's so great to see two cool guys sincerely discussing fashion. Thank you, fashion bros. Please do more videos together.

[@Pedro-ql4pq]

Man, even when I think a video topic might not be of my interest, I watch it for a few minutes and all of a sudden i've watched it till the end, thats how good this channel is lol. I got me some oversized sweaters hanging around that I used to wear as a teen but dropped 'em because I thought I was swimming in them and made me feel skinnier than I already am, but now that I'm gathering more info on how to dress myself I'm probably going to give them a shot again and see how it works out, regular/slim fit sweaters always make me feel confined in my movement, so hopefully it works out! Thanks a lot you guys, loved the video, the humour, and that sweater is absolutely fire, Tim, I need me one of those!

[@TimDessaint]

Thank you for your kind words Pedro! Happy to hear you're enjoying the content 😊 Definitely don't be afraid to experiment a little bit!

[@existentialcrisis9757]

Muscular and tight clothes 👎🏻

[@desanctisapostata]

Tim, what's your height?

[@armielbanez3318]

I love oversized and relaxed fit clothes, but with my built which is quite stocky and a bit short like 5'8 short sometimes i find it hard to pull it off. I take time thinking how to pull it off. But then Thanks to this video! Nice collab Tim and Daniel! Whew!

[@Grabehn42]

I like clothes, I enjoy wearing and trying stuff out, and that usually leads to some people asking me about it, mostly women, but I do know one too many women because of it that are just NOT aware of their bodies at all, both big and small frames alike. And while I still find it weird when people ask me about it, helping people out that way is really enjoyable, fulfilling even, when someone feels good about the way they look and you helped them get there.

[@uncannymannyii492]

Pretty sure at this point we just need Stevie Salle and my life is complete

[@Riileyrose]

His kiwi accent sounds so British that it sounds a lil’ South African

[@Urunatte]

It’s great video. I would like to see something where you are talking about clothes when man could wear women clothes and opiate, women wearing men’s clothes.

[@TimDessaint]

Thanks man! Suggestion noted 🙂

[@ThunderRazorYT]

Man, you guys rock this style so well. I have some relaxed fit and some straight fit items but they don't look the best on me. I need to try and follow your advice and up my game here. I think finding a drop shoulder tee that works for me will be the next way to start tying it all together.

[@TimDessaint]

Thanks man! For some good drop shoulder tees check out Everlane's premium weight relaxed t-shirt, and Uniqlo's oversized t-shirt (the one with the pocket). Different styles, both fit great 🙂

[@hectordb54]

El crossover más ambicioso de la historia

[@VampChainz]

I've an oversized CP Company linen button up for example. Wear it with straight leg Balenciagas. Guys should expand beyond skinnies. For the love of God lol also, those Engineered Garments?

[@teahousereloaded]

You know how and you know the why - amazing. Video would be easier to watch with less of you guys sitting and talking. I found myself rewatching all the examples several times, but then skipping through the talking part, just to come back and rewatch the talking sections eventually, because you make amazing points.

[@nguyentrannhabao9903]

I've been watching you for long time, I learn a lot. Im 5ft5, and I really want to know how tall you are

[@TimDessaint]

Thank you my friend! Glad you've been enjoying the content. I'm 5'7'' 🙂

[@oathquaker]

yo Tim how bout a video recommendation shoe showcase? ive really liked some minimal white sneakers

[@BicsGaming]

my two fav fashion youtubers in a collab.... never in my life did i think this would happen😭❤️

[@jeppemellbak3869]

"relaxed is gonna be a little more relaxed" lmao

[@schizophrenicdolphinz9822]

just bought 4 carhartt shirts

[@muze6142]

do more collaborations on each other’s channels this was great

[@urfuturehushbando9042]

"...In today's video, we're talking about porn" Ok Daniel

[@Jollopukki2]

" Just wear oversized overcoat over oversized t-shirt" )))

[@nicholaskelseysetiadi]

Two of my favorite fashion youtubers, nice.

[@legendarypillow1450]

I won’t lie, I’m not a fan of modern street dress, it’s kind of eccentric and odd. I myself stick with traditional dress, but you guys seriously look fresh asf.

[@bennyc409]

Dude sounds like he’s from South Africa with maybe just a few years in New Zealand.

[@helopeaplee]

I'm 23 and i'm 5'0, so i'm on the very short side. finding clothes for me can be very difficult because most adult sizes small and up probably will be too big, and searching in the bigger kids section is shitty because of cartoon prints and stuff. i was already looking in the women's section sometimes and getting a weird look sometimes lol. it's a fun but difficult "adventure" for me to look for nice clothes and in no way that i am insecure about my height.

[@TimDessaint]

The women's section is definitely full of gems! Also for basics, check out Asket. They make a different length for each size, so for example you can go for a XS, short, white t-shirt, instead of just a regular length XS. They're not cheap, but the quality is there and the sizing is very good.

[@pyranomics7229]

The silhouette and length on those (beautifully-colours) olive pants is so unflattering! I am sorry, this aesthetic is just not for me.

[@kiddid7363]

I’m sorry but the blonde guy has terrible sense of fashion. There’s being comfortable and there’s looking homeless and like you’re wearing hand me downs.

[@HuyTran-ie8jj]

Are you gonna do a haul or review of the new uniqlo u series this year?

[@TimDessaint]

Working on it as we speak 🙂

[@ToniVirtuosity]

Jerry Lorenzo take fault to the blazer and sweats. My opinion. In 2019 till now

[@pshdxt]

Avoid bad language*

[@brandondm_art]

I’ve been dressing with oversized clothes, but this video helped me to take it to a next level and have a better aesthetic 🔥

[@TimDessaint]

So glad to hear it brought you value Brandon! 😊

[@태이씨]

I absolutely love how the tucked tee looks like but i can't stand wearing it, don't feel comfortable this way

[@NicolasReinicke]

Truly love the video. It‘s the collab I really have been waiting for. Do you also think opting for oversized women’s trousers can be a good alternative as a skinny guy?

[@TimDessaint]

For sure! Clothes don't have gender. If a pair of oversized trousers in the women's section fits you well, get it 🙂