My Worst Outfits (And What You Can Learn From Them) | Men's Fashion Mistakes To Avoid

When it comes to developing our personal styles, we're all on a journey. And along the way we're bound to make some mistakes. It happens to the best of us--even me. Hard to believe, right?! :) Well, to show you that I've been there, in today's video I'm reviewing some of my worst outfits and providing some insights so you can hopefully avoid making some of the same mistakes that I've made in the past.
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[@pythonjava6228]

Honestly, your worst are better than a lot of guys best

[@lipton1cetea]

Your* this changes so much lol

[@pythonjava6228]

grammar police. I changed it😂

[@hespokestyle]

Too kind.

[@mohamedamrani7359]

Yes

[@Yaris510]

@@pythonjava6228 Well, while we're on the subject of bad grammar, there's a missing possessive apostrophe after the 's' in 'guys': '...your worst are better than a lot of guys' best'

[@zanejohnson482]

You should do a video of you re-making the outfits but with your critiques. Love the vids.

[@hespokestyle]

Seems to be a highly requested topic!

[@adamnelsonuk]

Humility and candidness are traits far too often missing on social media, love this video! Ace.

[@hespokestyle]

Thanks so much, Adam.

[@davidjea5648]

You should consider doing a contrast video of the “mistakes” on outfits and how to do the look better with benefit of experience and perspective.

[@hespokestyle]

Great idea! Like a follow up to this one?

[@christopherfoley2819]

That blazer rules, just gotta have the attitude and confidence to wear it. Prior to donning said blazer, a couple of Rye Old Fashions help

[@FloridaClay]

Enjoyed the video and critiques. But that jacket in #2. YIKES! Not even in the dark on a starless night!

[@CJ2345ish]

I really liked the cardigan outfit. I think if you wore it indoors (and therefore the cardigan is your outerwear) it would look great.

[@edoardogiordano531]

Humility, quality and honesty. My favorite channel! Thank you Brian

[@hespokestyle]

You're very welcome. Thanks so much for the comment.

[@Haske0]

IMO the only thing wrong with the pinstripe look was the shoes… the shoes looks way off…

[@hespokestyle]

Agree. I was going for a kind of laid back Italian vibe. Did not pull it off!

[@emilrandersen1]

Your pinstripe suit looked like you just watched Matthew Mcconaughey in The Wolf of Wall Street! Atleast that's where my head went. Otherwise your worst is definitely ahead of the competition's best!

[@hespokestyle]

Haha! Nice! Appreciate the comment.

[@kristopherchan4666]

Brian! Send me that blue graphic jacket! I absolutely remember when you posted that photo and I desperately SEARCHED for that jacket. I love it so much!

[@WomenHitTheWall]

Alright, in my humble opinion, the leather - jacket - outfit and the cardigan-outfit are super amazing. I will definitely copy both looks for the fall-winter seasons.

[@baskorohpradono7171]

On leather jacket i think just change shirt collar type and add more contrast tie and very well

[@DWilliam1]

Great video Brian. I feel a lot better about some of my mistakes. It reminds me when I had a single breasted 2 button suit made and decided to be “bold” with the jacket. Going for a kinda of retro Mad Man style I decided on a charcoal color with wide peak lapels, slanted pockets(including ticket pocket) and red stitching at the end of my sleeve buttonhole. It looks horrible. I keep it in my closet to remind myself to use restraint and follow some basic rules when buying a new suit or jacket. I still use the pants as a separate so it wasn’t a complete loss.

[@hespokestyle]

Ah, only place I wouldn't go is the contrast stitching. Personally, I hate that. It's too try-too-hard.

[@Berk1988a]

I think this applies to many people. It is all about mood, you feel that way then and then not. I loved a while ago the idea of a denim jacket and bought some. A year later or so, i dont even feel good about wearing them.

[@sorenwallin2535]

In my experience off-white is among the most difficult gear to mix with other colors. There is so many types of off-white. Mix in yellow, blue, red or grey and you get totally different types of off-white to match. I think, based on this experience, that the problem with one of your examples is the mix of ’yellow-tone-off-white’ with grey. Because some how the grey trousers are sharp and the shirt color just makes the shirt become ’damp’, in contrast. Given the compairing contrast of grey/white. I have a photo of myself in grey trousers/blue blazer/yellow-off-white shirt & it took me some time to figure out what was wrong. But it will be my suggestion for you, to make a vid on how to match different types of off-white?

[@hespokestyle]

Thanks so much for the suggestion, Sören!

[@leeanndesantana7841]

YOUR JACKET WITH THE CIRCLES IS FABULOUS. I THINK I WOULD KEEP IT FOREVER.

[@hespokestyle]

Thanks. It was one of the last pieces the Thom Browne did for Brooks Brothers Black Fleece.

[@bcross9109]

I actually like the first look with the leather bomber, I think the only issue is the rise of the pants vs the length of the jacket. The puffer coat with the shawl collar cardigan is definitely an iffy mix but not a total disaster

[@hespokestyle]

Thanks so much for chiming in!

[@NathanDodson]

Man, this video hurts lol. I'm just getting started into my personal style journey dressing as a grown man of my age, and I am already seeing that I've got a lot of learning to do. Some of these outfits I didn't even see a big problem with at first lmao. Dude, I'm glad KZbin put your stuff in my recommendation, because I have no idea what I'm doing lmfao. Thanks for your wisdom my man!

[@wolfgang9008]

Great content. Your outfits were not too bad. Like your channel. I think your channel is in the top 3 men's style channels on youtube. Continue the great work.

[@hespokestyle]

That's very kind of you to say. Much appreciated.

[@tonydeltablues]

I do like the fact you've posted these shots - yes they're not well conceived, but you are riht about the whole sartorial journey aspect. I'm a little way through myself and I need to look at some of my wardrobe and be ruthless. Thanks, appreciated. Tony

[@hespokestyle]

You're very welcome. Cheers.

[@bretmelton7116]

I can really appreciate your strategy of trying then reviewing! I find alot of things that I am doing that dont work like I thought later or dont age well

[@zhuoliu7967]

I bought my first striped navy suit today, really happy

[@yakramirez120]

Great video Brian, looking back always helps to improve, a video about your best outfits or the ones you like the most would be great too

[@hespokestyle]

Sweet! Thanks for chiming in!

[@garysmith1477]

Haha, I think the same of lots of my photos some of them are not taken so long ago. Like you said, we’re always learning. Appreciate the honesty.

[@hespokestyle]

Very welcome.

[@tiborszabo9616]

Brian, your worst outfits are better than the best of most people, that means you are doing a great job!

[@hespokestyle]

You're very kind.

[@ezracotter8675]

Love the video. Great idea and great content. While I think your comments were all reasonable, I also love that you're one to try new, interesting looks with pieces. Sometimes you strike out, with these looks, but I think the willingness to try them is what makes your style great.

[@hespokestyle]

That's really nice of you to say. Great observation.

[@Nathan-hs2ut]

Great video, learned a lot!

[@hespokestyle]

Thanks, Nathan!

[@Agerskiold]

It's obviously a learning process. I've done my share of 'learning' and I'm still doing it. When I look it that way it's ok - it was the part that made me, where I am today👍🏼 Cheers from Denmark 🇩🇰

[@rogerr.8507]

2:34 LOL. LMAO even. I liked the 1st out fit though, even the sunglasses you dont like, you just need to hop on your motorcycle sidecar and its perfect.

[@blackwidow3]

Failing by doing too much really warns me so thanks for sharing!!

[@hespokestyle]

Probably the biggest style mistake ever.

[@paulhughes5446]

Just catching up with your channel. Nice smooth presentation, video quality is way above the average of most men's fashion channels. Thanks for posting valuable information

[@hespokestyle]

You're very welcome. Thank you so much for the kind words.

[@bearzlla]

I like how your worst outfits are way better than most people's best outfits lol

[@lucasru1]

6 times he didn’t speek style

[@hespokestyle]

Haha.

[@djpcbaby]

I didn't think this video was even remotely possible! I have a LONG way to go because I loved the last look!

[@hespokestyle]

Nothing that wrong with it other than I feel that it is too costumey.

[@nukie404]

The look at 5:25 is my normal day-to-day sort of look, and I understand what you mean by saying it feels unfinished. However for me it also leaves a little room for experimentation when I want to dress up a bit more! Anyway I guess most looks you went over were more experimental, and I think that's a good thing because it shows us even the best of us need to put in effort, real sprezzatura.

[@hespokestyle]

Thanks so much for the comment.

[@desertfox432]

Great video with great points. The pinstripe outfit is actually not all that bad if you're feeling a Gordon Gekko mood. Wearing your mood when you have a sense of style works out most the time until you over think it or try too hard. It's fine to be extreme and if you're feeling Gordon Gekko, your air will carry it. The outfit might have been fixed with a reverse tie color pattern where it's maroon dominant. Great suit! Looks comfy.

[@hespokestyle]

Many thanks. Appreciate the thoughtful comment.

[@junhoson1462]

That complicated jacket is lovely.

[@hespokestyle]

Thanks! It is kind of funky.

[@kimfr3050]

I don't think there's anything wrong with the last outfit 🥰 it was so fun yet classic

[@hespokestyle]

Thanks so much for chiming in, Marc. Cheers.

[@26OY]

The first outfit is a smart casual, edgy yet in comfort zone colors style. I loudly disagree with your opinion. I think it looks good, I would wear it myself.

[@luischerrerafavela5329]

Great video! Honestly, I do not see anything wrong in outfit number 4. I actually like that is not necessarly trying to make a statement of any kind. Love your channel!

[@hespokestyle]

Many thanks, Luis. Appreciate the comment.

[@ianarn]

The 1st is good! The others have various problems with them. I like ties but don’t like the bow tie look outside of a dinner suit combo!

[@hespokestyle]

Thanks for chiming in, Ian.

[@tomaszgajownik9939]

Brave. Courage. The best way to learn others to avoid some mistakes. Chapeau bas👌👌👌👌👌👍👍👍👍👍

[@hespokestyle]

Many thanks, Tomasz. Glad you guys are digging this one.

[@sbiswanger]

As an interesting highlight of how individual tastes are, I didn't always agree with your critiques. For example the leather jacket outfit, I expected you to point out the similarity of the patterns in the tie and pants and lacking contrast to help anchor the outfit. Even your worst outfits, are exceptional. Thanks for being open and showing us it is okay to experiment. The only way to identify "too far" is to get there and then take a step back. My sense of "too far" is so much further than it was at first and so different than others (I'm looking at you Milan)

[@hespokestyle]

Thanks so much for the comment, Steve. Much appreciated! Cheers.

[@clerouxbotha2784]

2nd look with crazy blazer....i like it cause its a bold statement. Without the braces though.

[@beerserker]

This was really good, am remembering some of my outfits from three or four years ago. I definitely overdid it. Great channel!

[@tjs5770]

I really appreciate your willingness to put yourself out there and bring up looks you’re not proud of. When were these taken? Some of them look like they’re from the mid 00’s when #menswear became a thing. Especially the last one. I was kind of the same way when I first got into style, trying to do way too much before I really understood what looked good on me.

[@hespokestyle]

Most of the looks here were shot around 2013-2014. Right at the start of HSS and right when the online thing started to gain some traction.

[@misha9952]

Great video as always! The only one that is really offbase is the last one (like you said a bit too costumey). The pinstripe suit one is actually not that bad with some minor tweaks. Looks very sprezzatura or something an italian gentleman would wear. The rest are just a bit of mismatching but are still better than 90% off what guys wear out in the wild.

[@hespokestyle]

Many thanks for the support!

[@renebrito6423]

Great video, thanks for sharing! What I take away is less is generally more, thank you again, great video!

[@hespokestyle]

Thanks, as always, Rene. Good takeaway.

[@jud133]

watch you forgot you buttondown underneath a turtleneck. That look is definitely up there with these.

[@hespokestyle]

Disagree. But thanks for chiming in.

[@geoffkeough9728]

the cardigan outfit sans that jacket looks good i think...

[@Ryan-by8ui]

Last one looks like a Peaky fookin' Blinder!!!

[@119Agent]

I did not have KZbin to help learn about style and fashion when I was just getting started.

[@hwadinskij7495]

your worst outfits are better than my best lol trying to better myself though

[@anthonyjo2816]

Hi Brian, your presentations generally always meet with my expectations, including this video. Keep making inspiring videos and share them to the world. GBU ! Kind regards from Jakarta

[@ConkreteMan]

I would definitely be interested in that wild sport coat, however my wife would kill me if I actually spent money on it. ☹️ Enjoyed your comments on the other looks and appreciate the thought process as the why you did it and what you don't like about them now.

[@hespokestyle]

Haha! Many thanks for the comment.

[@ajwise121]

I actually like the last dapper outfit, do you think in the right city, say London or other parts of Europe this would be perfectly fine? For me the biggest influence in style is actually climate and context of the city you’re in.

[@hespokestyle]

Meh, idk. Maybe like 7-10 years ago. But it's just trying too hard these days, imo. Would look great at the Jazz Age Lawn Party!

[@lezmajz4677]

I like the last one , is not that bad.

[@hespokestyle]

No, it's not. It just feels too costumey to me.

[@JT-rx1eo]

Yes, that spotted blazer is terrible. The look with the newsboy hat, grey vest and trousers, and burgundy bow tie is a GREAT look. But, yes, it looks like a deliberate retro wear, like a photoshoot occasion.

[@LGTeGeTeGe]

i like the jacket of the second outfit, but i agree that it was not used correctly, so i would like to see an example of how does it could look cool

[@ankurbamne7155]

I love ur content Brian, keep up the good work. Big fan here.

[@hespokestyle]

Thanks so much, Ankur.

[@Dzamora612]

Great video! Nice approach and humility in taking an older self critique. Would have made it a little more fun to watch with you facing the camera, so we get your face reactions to the looks better. Either way, great content 👍🏻

[@hespokestyle]

Thanks so much, Daniel.

[@qarhsi]

I'd say that all these looks are much better than majority of the ppl out there. I would say that the 2nd and 1st looks are the more questionable ones. 3 was actually good, just didn't like the choice of shoes. 4 was decent too, felt that the jacket should have been buttoned and it looked a bit baggy. Last look is cool, but yeah like you said, you were trying hard to get a certain vibe I guess. Cheers!

[@hespokestyle]

You're very kind. Thanks, as always, for the comment.

[@qarhsi]

@@hespokestyle :D

[@DonaldSjervenE]

Those pants in that first outfit are like those from my dad's favorite suit. Mom hated it. She got rid of it. Dad's buried in it.

[@arifsevimli4324]

I don't understand what you dislike so much about the first because it looks great.Only thing that doesn't look bad but could be better would be the shirt collar.With the pinstripe,yes too much going on but it would still work with different shoes.Second one...is that you?

[@bubbie23jw]

I like the last one I would rock it

[@hespokestyle]

Cheers!

[@pratman8]

Hey Brian! Love the videos, and especially the watches, as I’m a watch guy myself! What size is the blue and white patterned blazer, and how much for it?

[@hespokestyle]

Awesome! It's size BB0 (basically a 36). It's Thom Browne for Brooks Brothers so it is on the shorter side. I'd part with it for $300. That's more than fair based on what this stuff is going for on eBay. The Black Fleece line was discontinued a few years ago.

[@pratman8]

He Spoke Style unfortunately that’s a little small for me, but I love the design!! Keep up the great videos man!

[@fariqwalker]

Thanks for sharing this video. I'm sure that not a lot of people would admit that they made mistakes in the past and would just have bury them. looking forward to the reaction video for the upcoming pitti uomo ;)

[@hespokestyle]

Haha. Not sure I'm going to do one, but thanks for reminding me! Wasn't even on my radar.

[@davidmcnicol5322]

Brian, I always thought of you as a somewhat urbane, very stylish and sophisticated man. Seeing you in that black & white jacket, I now realise you’re not!!! Thanks for sharing. ❤️D.

[@hespokestyle]

Haha.

[@oliveralaviuhkola4834]

I think I could possibly pull off the blazer. I should have good shirt and tie with it just need pants and shoes. The size isn't a problem i know a tailor who can customise it to my size.

[@hespokestyle]

Asking $300.

[@jinyoon5149]

Loved the video! Lot of knowledge in this. With regards to your last outfit, what do you mean when you say it’s too affected?

[@hespokestyle]

Many thanks. What I mean, is I feel like I am trying too hard.

[@tidalgardens]

On the second outfit, I think the blazer could absolutely work, but everything else has to be toned way down.

[@hespokestyle]

That was actually the point of the post--to let a statement piece stand on it's own. Obviously, I didn't pull it off so well.

[@daniellowery9618]

Can you elaborate on the collar you wore on the first outfit? Is there a specific reason you chose not to wear small collars anymore? Or just personal preference? Thank you!

[@hespokestyle]

Sure. Honestly, it was what was available to me at the time. I bought a lot of my clothes at J.Crew, which deals in smaller collars and thinner lapels. This is something you find in a lot of mass market menswear retailers. No getting around it. Brooks Brothers has better choices.

[@marcogonzalez4615]

Cool video. I’m curious though, would you say the fabric of a leather jacket and wool trousers don’t mix well?

[@hespokestyle]

That's what I said.

[@TheJacobLentin]

Actually love that jacket it’s too cool not to wear!

[@hespokestyle]

You interested?!

[@TheJacobLentin]

Absolutely!

[@ichbin2361]

As you said, it's a journey, mistakes are inevitable (errare humanum est). That's very brave of you, to share the mistakes, in this perfectionistas world. Funny thing is that I live in a small town and it happened that I often see people literally in every look you shared, 5-30 is definitely not a bad look, a bag would improve the look, in my opinion.

[@hespokestyle]

Many thanks.

[@herebarian]

I know I’m commenting on an old video, but KZbin keeps recommending me things from before the pandemic, so I don’t know what’s going on. Anyway if you end up doing something similar in future, maybe you could give us tips on how you would improve the same outfit considering your evolution in tastes and preferences. Cheers!

[@stevefield9967]

What size is the Jacket? I think it may look OK with a pair of white trousers.

[@hespokestyle]

It's a BB0 (basically the Brooks Brothers Black Fleece equivalent of 36).

[@dismasjoseph7313]

Good video - well put together.

[@LANKESH_WORLD]

I am from india i watch your video for learning english😀. And literally i am learning this, thank you sir.😍

[@BespokeBandit]

'You know you have improved greatly when you cringe at your past'

[@brentl.vaneaton6901]

Great topic although thinking about some of the mistakes i’ve made really makes me cringe... sartorial moments of shame ☺️ just imagine football pants that are really tight shorts and a mid drift T-shirt nothing could’ve been worse, ok I was in high school then but still hate thinking ‘bout it

[@hespokestyle]

Yikes!

[@andrewbeldin659]

Good on you for making this video. I've been wanting to pull the trigger on a classic leather jacket. I haven't found one I like particularly well. I'm in the PacNW so we are very casual in the main. A lot of the stuff I see is more modern but I have a more classic sensibility. Any thoughts on good brands/places to look? I kind of like the idea of bomber style but hold any shearling.

[@hespokestyle]

Hi, Andrew. My leather jacket is nothing special--it's by Topman. Have had it for about six years!

[@nutyyyy]

Looking back on my first forays into classic menswear at 18 makes me cringe a bit. I still look ok due to my height but even so it's amazing how much you can learn through experience and research both online and by talking with those in the know.

[@fastleopard1]

Very interesting perspective on your sartorial journey

[@hespokestyle]

Thanks, Steve!

[@DemetriosLevi]

Wow...your worst is better than most of my outfits lol but I definitively understand where you're coming from with the criticism. Take a look at any of my old instagram photos and it's easy to see mine lmao I was a sucker for ultra saturated colors and accessories. I did the typical "if these all look cool on their own, they'll look better when worn together". Great video as always, Brian!

[@hespokestyle]

Thanks so much, as always, for the comment.

[@d3vi0uz1]

That "worst" in the thumbnail would actually be considered retro these days, thus acceptable.

[@hespokestyle]

Cheers.

[@westfieldartworks8188]

Hmmmm, can't really agree that these were bad outfits. Maybe bad for you, but geez, great for the rest of us. I'll agree on one point; I think they are all great outfits that are about 5% - 10% off on some of the details. but that's it. That said, it's nice to hear some self critiquing from one of the pro's.

[@hespokestyle]

Appreciate the comment, Anthony!

[@Myrslokstok]

Ha ha ha you think that was bad 😃 It is still well over average! Except the #2 blazer it would probably be top 10 looks for any average guy. Thanks for sheering it is probably a bit painfull. I put some logos-patches on my jeans, and then I was a bit pissed when people told me thet I looked stupid. 😬

[@hespokestyle]

Thanks so much for chiming in.

[@jimwhite8351]

the jacket with the white and blue octagons - now if the wall was painted the same way. you could have been blended into the wall

[@Gouveia100]

The last one wasn't bas if you remove the oversized hat and chenge the bow tie for a tie.

[@oscargustavoarcosruiz8793]

Oh ... My ... God ... the second Outfits is too much for me :-D But you can say that it looks interesting, and you learn as much from mistakes as from successes. The third one seems to me that it would look great in Pitti Uomo, personally I like it. The last one is not my style at all.

[@hespokestyle]

Thanks so much for chiming in.

[@somewonderfulguy]

Few times you said that that glasses do not match outfit. Well... could you say how does glasses should fit to outfit?

[@hespokestyle]

I think they should complement the overall vibe and color palate. I'm a more conservative dresser and these were attempts to stretch that I don't think worked looking back on it.

[@DareBearTD]

I'd be potentially interested in the jacket if its a 36!

[@hespokestyle]

Brooks Brothers Black Fleece had their own sizing. This is a BB0. I typically wear a 36 and it fits great.

[@apolinarioenglish]

Thanks for the jacket, Brian. But no... lol

[@hespokestyle]

😀

[@mcneelynorman1]

Love the video. Like the last comment, if you could take from each piece what you liked about it and how now, you would make it work, that would be great.

[@hespokestyle]

That's a great idea.

[@eminafandibayli7094]

With the double-breasted blazer photo I guess, the missing piece is related with shoes. Great video, and I do respect how you could judge yourself.

[@hespokestyle]

Thanks, Emin! Appreciate you chiming in.

[@Jjf109nine]

5:37 missing a white pocket square

[@KuIJohnQ]

Brian, what's your opinion on wearing regular hemmed trousers with a double breasted jacket, as in Look #4? I've always thought that double breasted jackets (even the more casual ones) only look correct with cuffed trousers, but maybe that's not the right assessment.

[@hespokestyle]

Plain bottom v. cuffed is a personal choice. To be safe, plain bottom for more formal events, cuff for anything else.

[@Axel2Blue]

What watch are you wearing in the first outfit? At 2:21

[@hespokestyle]

It's the Victorinox INOX: shopstyle.it/l/4mPL

[@douglasyong6939]

How would you dress up a leather jacket, especially as a more mature person?

[@hespokestyle]

I think the main issue was the trousers. Something in a sleeker fabric would look much better.