7 Downsides to Being a Well-Dressed Man 

Dressing well also makes you realize how ugly the world around us has become, I will always choose beauty and elegance over repulsiveness !

I once heard someone say: “if you are overdressed you might feel ridiculous, but if you are underdressed you are ridiculous.” Love that quote.

One of my favorite quotes is from Tom Ford "Dressing well is a form of good manners."

"Dressing well is a form of self-respect"

Dressing well is about respect. It is respecting yourself and others.

Handsome men are usually hated in public spaces. You will receive positive attention at first, but people will always look for a reason to spit venom and discredit you if you stand out.

ZZ Top said it best, “all the girls go crazy over a sharp-dressed man!”

My job is not to intimidate the poorly dressed. My job is to encourage them to up their game:)

The worst thing about wearing a suit in public is when people assume you're staff. "I'm so sorry, I thought you were the manager". "I appreciate that ma'am, but this is a hardware store".

I was interested in a girl, I ran into her at a coffee shop, and sat with other people. I had a fresh hair cut, trimmed mustache, a blue polo shirt, and one of my best watches..a new pair of jeans, and one of my best shoes for going out..shined to perfection. If I wasn't in work clothes, I always dress nice and casual. She said in front of me that I was too well groomed, dressed too nice..if she wasn't interested, she could have been more mature but she decided to go low when I went high. I stopped seeing her that night. My ex wife had a similar problem... picking apart my outfits but I ignored her. Gentlemen, I believe that part of dressing nice is being with someone who doesn't try to dim your shining light...let her if she does that.

Being a well dressed man involves “owning the look” meaning if you are not confident or comfortable how can you make others comfortable around you.

I’m 23 and the only downside for me is I’m a mechanic and work on classic cars, so I only wear suits on the weekend’s. Though I still try to look nice by wearing a pair of classic brown overalls and a watch. I’ve ruined a couple of good shirts with oil stains because I always end up working on my own cars at the weekend 😂

I found a treasure yesterday in a second hand shop; a men’s made in England wool three piece suit in navy blue, never worn! I paid 40€. I am taking it to my tailor for adjustments. It is gorgeous, I am really thrilled!

"Being well-dressed doesn't mean being overdressed." 👏It's always good to see another style video from you!

A downside for dads of small children is keeping them from wiping their faces and hands all over your clothes 😂

There is zero downside to being a well dressed man 👌

Looking good is a polite way of putting the world around yourself On Notice, that you Expect Better.

If you dress to feel good about yourself then someone else's insecurity or lack of self esteem should not be your concern. Society nowadays is lowering itself to the lowest common denominator. If a slob feels bad about his dress that's his problem not yours. He should raise his style not cause you to lower yours.

Great topic Gent Z... the only 'downside' would be if you are too self-conscious about dressing well it will be too obvious to others. Also, when you encounter another gentleman with impeccable style, sincerely compliment him (brevity is best here) as he is not your competition but rather, your sartorial ally. Salut!

Since I started dressing better, I've gotten a lot of compliments and even total strangers asking me what I do or sparking up a conversation with me because I seem more interesting. Having said that, I do see many of the same negative comments, jokes and eye-rolls coming from people close me as when I started taking exercise and going to the gym more seriously. People are very uncomfortable when you try and improve yourself. They oftentimes want you to be 'the same' person, not take risks, and stay stagnant to make themselves feel better. Sometimes this comes from a place of love. Sometimes it's people just being petty. I think dressing well is a great value, and people who dismiss it are often just insecure.

When I was younger, I felt and acted nervous around attractive women. Now that I'm older and successful, it's fun to see them get visibly flustered around me when I wear a suit.

Two downsides, I have experienced, are the poking fun at me for dressing better than them. The other is that it is hard to do when it is warmer outside and you want to dress in a suit or sport coat. Linen is nice, but summers, here, are hot and humid. I look forward to falls and winters.

I work around a bunch of hillbillies. Every time I come to a staff meeting I’m well-dressed (not at all fancy, as been suggested - which tells me a lot about them), I’m overly complimented on my attire. I’m like, REALLY?? - I’ve got jeans and a button-down linen shirt on. Wtf??

Biggest downside when dressing sharp is the fact that every time before you leave your home you get the feeling of always having to prepare yourself to put up more of a shield or guard to protect yourself from the possible malicious behavior you might encounter from public society (Southern California). Thankfully, my slim kind of muscular look helps give me the confidence to protect myself both physically and mentally.

Regarding #5, I am currently living in New Mexico, not exactly a hotbed of style. However, the other day I was at my favorite coffee shop (yes, there are coffee shops in the high desert) wearing blue jeans, an olive green shirt, and a blue handkerchief around my neck. I encountered a woman I know who was there with a female friend. Later, she sent me a text complementing me on my look and telling me her friend was "wowed" by my style. Women notice well-dressed men regardless of where you are - and as you stated, they like it.

I like to dress nicely but it is uncomfortable when I do so around mine and my wife’s family, who dress in gym clothes, sweatpants and cargo shorts. However, I choose to stand out and enjoy how I look.

Dressing well is our personal signature we sign onto the world!

Mate, I feel you on this. I dress like a British Mod circa 1964 and I’m shocked how many people wearing greasy Walmart clobber have the temerity to be hostile towards me due to my manner of dress. Keep the faith!

Very well said…as a 26 year old from Singapore 🇸🇬…even if I dress casually from a sartorial point of view in appropriate scenarios, I’m still perceived as “too formal” for everyone. Even though deep down I know I’m dressing causally, everyone still perceived that I always at work…

When I dress well, some people think that I am showing off and just trying to draw attention to myself, but, really, I dress well out of respect for my fellow humans and to, maybe, inspire other men to up their game, and, well, it just feels good to be well dressed

The insouciant disregard most men have for their appearance is of no mind to me. Why would I need a comparison? A college student ask me, the professor, why I always get "dressed up"---when apparently none of his other professors seem to care. I replied I do it for them, to honor a shared commitment to dignify the work and to encourage them to up their game, in fact every bit of the game they are playing. If clothes are understood to be superficial, frivolous, and un-masculine, show people the opposite. Instead of comparisons and expectations, I try to meet them with examples and opportunities.

Pls do a video on gentlemen’s lounge/ comfort wear and alternatives to sweatpants

I started dressing better after getting admitted to professional school,and being inspired by the first season of the television show "Ray Donovan". The negative feedback I received from co-workers,truly got me off-guard. But I knew I was dressing for where I was going,not for where I already was.

I always respect someone who took the time to put themselves together well, men and women. I am trying to be better. I wish i had a friend group that also was well dressed

I live in Japan, where people mostly dress well already. It’s harder to compete and stand out. Here the oversized look has been trending, so I have to look harder for clothes, often online, to get the fitted look. Still it really sharpens my style being here.

Being a 23 year old man that enjoys dressing well everyday I cannot describe how precisely true this video is. However, I often feel like I intimidate people when I meet them for the first time. Some people will remain unshaken (mostly outside of the professional world), but I've found that the simple fact of wearing a jacket puts a gap in people's mind and I feel like it's now harder for me to make people comfortable around me and have them open up. Do some of you experience the same thing or is it just me?

I am on the old end of Gen Z. I have completely built my wardrobe secondhand, while also learning how to sew and do some tailoring in the process. It taught me how to understand the different cuts, what is flattering for my body, and how to be critical of construction and fabrics, but the latter being a credit to my wife who is a handweaver. While the suits and sportscoats are nice and all, also pay great attention to the supporting roles; dress shirts, ties, slacks, belts, shoes etc. They all have a huge impact on the flexibility and success of your wardrobe and are more common than finding a goldilocks suit or sportscoat. It was difficult to comprehend this when I first started, but personal style is a process that takes years to evaluate and grow into.

I have a lot of suits and its my uniform of choice for everyday wear. Even on the rare occasion when I go to a fast food restaurant. One time I was at a pizza place in Seattle and the cook comped my meal. I was very thankful and curious about the gesture. When I asked him for the reason of his act of kindness; he replied; "I figured you were someone famous or important because I have never seen anyone dress in a suit like that in a joint like this." It was extremely flattering.

Downside is in the summer dressing well often leads to sweaty situations

One downside for me is I can't just leave the house for an errand like slobs do, but have to go through wardrobes to see what I'll wear.

Dressing well has the twin effect of generating: 1. positive compliments 2. negative compliments It is a litmus test separating the people who care for your success and welbeing, versus those who do not.

Buying high quality clothes but fewer, carefully chosen, that will last and go out of style slowly if at all, will cost no more and maybe less that constant impulse buying of cheap clothes. A friend of mine as an undergraduate in the ‘80s, when reproached for wearing shirts with collars, replied, “My ten real shirts cost less than your drawers stuffed full of T-shirts.” A priest I know who grew up in dire poverty, said, “Poor people can’t afford cheap shoes.”

My everyday clothing in my wardrobe are trousers, dress shoes, knitted polos shirts. I also wear suits because of my job; after all, I'm a bespoke tailor.

I was with friends on a holiday in Italy and we were getting ready for dinner out. I was wearing a button down and blazer while they put on a t-shirt. They got angry at me for making them look bad so I told them to instead come up to my level and put a nice bottom down. It worked.

I am influenced by the message of: Pay attention to what you are doing. Do not rush, don’t get excited about the novel, enjoy the self-care. Working out, writing using a pen, studying topics that are worthwhile, be considerate and help others. Be who you want to be, not what others tell you what you should be like.

I rarely ever get insecure over what others wear, my main insecurites come from physical features such as me being on the shorter side and having pectus excavatum.

To me, "dressing well" means dressing appropriately for the occasion. It does not mean looking like you just stepped out of a haberdashery or overdressing for an event or place. I am a 75 y.o. retired lawyer and have had nice clothes my entire life. Whether you are dressing for work, a casual occasion, vacation, church or dinner in a restaurant, my advice is to stick to classic understated and tasteful choices rather than in the latest fashion. If you do that you will never fail. Frankly, I wouldn't be caught dead wearing some of the clothes you see in men's fashion magazines. And don't forget about shoes. Nothing looks worse than a dressed up guy wearing a cheap pair of shoes or shoes badly in need of polishing. I don't see any downside to dressing well as long as you are not being pretentious or trying to impress someone.

Sizing is a big part of this. To look great, clothes must fit the wearer.

I am constantly amazed at the lack of comprehension of most men who cannot discerne "black tie", "business casual", etc. T-shirts and jeans don't cut it!!😉😁

I just started my first job, which is a hosting position at probably the nicest restaurant in town, and the uniform is a black waistcoat provided by the establishment, as well as black pants, white button up shirt and black shoes. I regularly wear three piece suits with a pocket watch, ties, etc. so I feel very 'dressed down' in my work clothes, whereas I'm sure my coworkers feel almost as though they're dressed in the pinnacle of fashion

I met some friends for dinner recently at an upscale restaurant. My friend prompted us to be "well dressed" so to avoid disappointing him I went full 3 piece suit, tie, camel overcoat and dress fedora. Bit OTT but man did I feel good being dressed to the nines, shiny shoes and as I was complimented by maybe 7 people apart from my 3 associates for making an effort, funnily it was easier to be well dressed than to be underdressed.

I reside in a small community in the Midwest. Even so, I've been amazed by the quality clothes I've found at a secondhand store, here. I've bought several overcoats (including wool ones), that are in mint condition. Bought some suits (including a very nice pinstripe), and a pair of Florsheim Imperial wingtip shoes. Again, all in mint condition.

Dressing well is a matter of self respect, because you should always do it for yourself.

When I started dressing significantly better, especially for work and work travel, I've faced with some weird reactions from my colleagues (poorly dressed, I should note). One said, half-jokingly, that I'm probably having my mid-life crisis (I was about 39 back then, 40 now). What do I think of that? I cut such people from my circles and don't spend time with them.

As a retired prosecutor, my usual office wear is Brooks Brothers suit, highly polished shoes, starched and pressed dress shirt ajd pressed Brooks Brothers tie, tied with a proper dimple on a 4 in hand knot, and braces. I've got to look like The Man. What is interesting is even when I am out of court and going to lunch in town, people will usually step out of my way, or let me through the door first, or get served by the waitstaff. You create an aura. You present an image of a serious professional. You get noticed as someone who dont suffer fools gladly. In the 1970s John T. Molloy wrote a book titled Dress for Success. In the book, he examined the effects of good serious clothing and the attributes it can elicit. He advises on how to dress conservatively but well, rather than dressing fashionably. He concludes that dressing well elicits good positive attributes and higher respect.

Vibe of the video 😂 “Look at that subtle off-white coloring. The tasteful thickness of it. Oh my God it even has a watermark.”

When the world is hectic or sad, I find myself going to your channel. And I'm female! It reminds me of days gone by and several of the gentlemen who were my colleagues and friends. Alas, many have gone to the old Brooks Brothers in the sky. Brings a smile to my face and soul. Thank you. -Retired in New Mexico.

Excellent video! You make excellent points. Yes, you will be either praised or ridiculed for your dress, especially if you live in parts of the country where causal dress is the rule. For young men, I recommend building your wardrobe over time, and dont worry about being over dressed! Be a trend setter! I find all lot of men would rather get a root canel than wear nice dress clothes, shoes and a tie. Its having a mind set on dressing like a gentleman.

I have an idea, find an average guy, dress him up in a fine suit, like a Brooks Brothers, Tom Ford or whatever, teach him about style and etiquette, set him up with all the right people, that would make an interesting video!

I love your authenticity gentleman. Never stop the good work!

To address the second point you made about clothes shopping being expensive, I have taken your advice and started shopping at thrift stores and have really gotten into it. My wardrobe has expanded greatly with stylish new pieces. Now, the biggest problem I have is getting that darn Macklemore song out of my head.

Love the mood and content of your videos. You are a positive influence and for this, I thank you!

As a radical Christian-Conservative, i like to dress good and modestly. Thanks for good video

It is simply a personal choice in how I dress. My wife loves the way I look when we go out. We both try to compliment each other. You have really good comments on style. I have gained some tips from what you talk about, thank you for your insight.

For decades suit and tie was my daily office-wear. Now that I'm retired, I still have several suits and a whole collection of ties in my wardrobe, but no occasion to wear them. Even when I occasionally dress up to go to a wedding, I'm just one of two or three funny-duddies wearing suit and tie. I'm glad I can wear jeans and T-shirts, but I really miss dressing up from time to time. But then I don't like standing out in a crowd or being judged as feeling superior.

For me the downside is that sometimes I don’t have the emotional bandwidth to properly engage with people when they want to speak with me and I have to wrestle my gentlemen’s demeanor with my inner fatigue.

In regards to the second hand garments, I did some quick math and my wardrobe has a retail value of approximately $40-50,000. I have built it over the last five years for roughly $5000. Almost everything is Brooks Brothers, Canali, Zegna, Eton, goodyear welted shoes, etc. All 100% natural materials, wool, linen, cashmere... Literally pennies on the dollar. This isn't to brag on the clothes just my frugality and that second hand is a great option. Maintaining it all is therapy for me. I genuinely enjoy doing it.

No.2 is a good point but I personally shop at goodwill and antique store, “why goodwill?” You may ask, well, they have hidden gems and high quality vintage pieces. I found a 2 piece double breasted navy suit that fits me well at a goodwill for 20$. I found my trench coat at goodwill for 5$. All my ties and shirts are from goodwill and they fit me perfectly, but I would recommend washing them before putting them on.

Excellent Video 🥃🔥 1. Sometimes I dress down too 2. I dress semi-formal 3. Yes, I do get anger at me but being 6 Foot 5 Inches tall, no one is messing with me 🤣 4. To the Occasion is Correct ✅ 5. Sometimes dark jeans with a suit jacket feels nice 😊

James, your heart is definitely in the right place. I am a lady of some years and I would never reject the sight of a well dressed gentleman as there are so few these days. Thanks for being a shining beacon to men who really, really need a clue!

Always dress very well for the occasion. Never overdress. Make it look like you are effortless, however, it is clear you have it all together. Don't be flashy or stand out. I can wear a blue blazer, nice jeans, an oxford shirt, a Rolex Submariner watch, high quality penny loafers or tassel loafer to nearly any occasion possible. And look sharp doing it.

I have tried out buying used clothing from eBay and have been happy with the results. I got a pair of dress shoes that are quite good and I found a Brooks Brothers sports jacket for $40 US that I thought was a great bargain.

Note: I've purchased many "new" items on eBay. So eBay does not necessarily mean "used" - typically however it means less costly. Good vid. Keep at it!

It's important to remember that style is a personal expression and finding a balance that feels authentic and comfortable can mitigate some of these challenges. 👌

A little vignette regarding dressing like an adult... I'm a retired teacher of over 30 years experience. I attended teachers' college in the late 60's and at that time teachers were expected to dress properly, to show the world that you meant business and to provide a good example for your students. Men wore a shirt and tie dress pants and polished shoes. As time marched on expectations of dress seemed to dissolve. But I continued to dress in a professional manor and thought nothing of it. Towards the end of my teaching career, I was assigned a new school. I went to introduce myself to the principal. She was very welcoming and commented on how well put together I was, or some such thing. While we were chatting a very young man approached dressed in blue jeans and a bowling shirt. I was surprised when my new principal introduced me to the young man as one of the staff members! No sooner did we shake hands, when he remarked, "I hope you're not gonna come to work dressed like that every day!" Can you imagine ?! Our principal was standing there with a shocked look on her face, not knowing how to back pedal the young man's rude intro. I looked him up and down, then, looking directly at him, I said, " Well son, if you can show up looking like THAT, i can arrive for work looking like THIS!" He was non-plussed. Our principal looked at him and said, "Well, I guess he told YOU!". That's not only a commentary on the deterioration of proper dress in a public place, but the decline in decorum and basic civility.

Wow you absolutely took the bathroom incident the wrong way. For me ,whenever I see another well-dressed person, it makes me happier, especially if they are dressed far better than me. I draw inspiration from them and it also lets me know that I am not alone in my sartorial journey

Never thought I'd find this sort of content so interesting. Keep on, lad!

Look at pics of gents around the early 1900's. Every man wore a suit and hat. Even the kids! Folks didn't have a lot of $ but a lot of pride in themselves.

On the "spending more" part, oh boy... I definitely agree with that one. I keep trying to cut on my clothes spending, but I always find something to want :)). At the very least, I don't have a big wardrobe and I hate clutter, so that keeps me mostly in check.

Dressing well has caused me to be targeted by a narcissist.

It’s true that it can cost a good deal of money, I personally wish I could invest in an elegant three piece linen suit for my sister’s wedding next month but I simply can’t spend 600-700€ so I might just head to a second hand store or something and get a more affordable attire although it may not fit properly or be a good fabric. However, I despair not, this frustration is a great incentive for me to push towards getting out of my comfort zone and upgrade my life !

Nice video. These are the common issues that I experience also, and you stated them well

Stand your ground. Decorum, beauty and elegance are worth fighting to preserve. Never doubt that the higher standard is the better standard. Lead, unapologetically, by example and others will follow.

My biggest challenges: When I decide on a new style and need to let go of old styles. For example, tie color and vest style. Deciding if I want to use hair regrowth treatment or let my hair go. As for some of the problems you mention, I have a few solutions. There are tricks to look sharp while dressing casually. I never go below smart casual. A trilby hat also helps. As for money, I do a minimalist wardrobe. Thet's when I look like a cartoon character and wear the same thing. Same color tie and suit. Same color and style vest. The best way to build a minimalist wardrobe is to like something so much, you just can't wear anything else. It causes me to spend less.

You hit some good points, thanks. One that I encounter involves uneven requirements. I volunteer at a charity where I normally just talk to people, but occasionally I’m required to risk clothing cleanliness or even damage as part of the job. I’d prefer to dress well but lean toward high quality utility (e.g., Duluth Trading).

I can resonates with some of these. Good quality clothing does cost more but is worth it because it lasts longer and you need less garments overall. Plus I have saved a ton of money on ebay. I just bought a newsboy cap for half of what the upscale hat stores charge. You also stand out more now then you would decades ago. I am usually the best dressed person in the room. I have received numerous compliments however, usually from women.

Even just well fitting pants and a sport coat with nice shoes would look 100× better than the stuff people usually wear

Video on going to a cigar lounge please. Intimidating to go in first time. Thanks

Thank you for this video James. I’d love to see a series of videos about second-hand shopping and what to look for. I’ve bought a few sports jackets, trousers, and accessories from sites like Mercari and EBay in the US. I think it’d be a great help for those of us on a budget and are just getting started or want to try something new without breaking the bank. Thanks

I deeply appreciate the Bauhaus posters in the background

Amazing video, amazing tips, amazing clothes.

I am a watch guy, and this ethos applies to the watch world as well. When you first start out, a shiny Casio or inexpensive Seiko is like a pot of gold. But as you delve deeper into horology, and you experience better, higher end watches like Omega, Rolex, Longines, Breitling, you see the meticulous craft of the movement, the polish, the finishing, and suddenly a cheap $2~300 watch with a Miyota movement seems more like a fake glass compared to an actual gemstone. Except G-Shock. G-shocks are always cool. But it's the same with dressing well. Once you have a tailored jacket, proper fitted shoes and pants, it really brings out how bland "regular" clothing can be. Nobody NEEDS a $5,500 Omega, any more than you NEED a $1,800 tailored suit. But nothing replaces that sense of appreciation it brings, and the self confidence and self image. It truly exemplifies the saying, "Dress well, feel well." I honestly believe this is one of the things plaguing global society right now. People go out dressed in sweat pants and crocs, and nobody cares about their appearance, in general society, I mean. Also, I want to stress I'm 48, and am not a handsome guy. You can't make a silk purse out of a sow's ear. But I still appreciate and feel more confident dressing well. When I was a kid in this far off, distant land called "The 80's", we still got dressed up to go out to dinner. It was a special occasion, and we, as a society, typically had self respect and awareness. Women dressed in nice dresses or blouses and pants, men and boys dressed in jackets and dress shirts, if not ties. Dinner and a movie for the family was special and demanded the proper attire. Nowadays nobody seems to have that self respect, and when you dress poorly, it reflects in your psyche. I'm a professional driver, and I have rare opportunities to wear fancy clothing, but it makes the occasion all the more special, and when I and my friends are dressed well and sit down in a restaurant filled with slobs in wife beaters, fanny packs and $8 wal mart shoes, I don't give a shit what they think or how they feel. It's rare I get fancied up, but when I do, it feels nice. Maybe if some younger person sees people dressing nice it will inspire them to do so as well. "Influencers" should keep that in mind.

#2 Maybe. Branded clothes that don't last cost more than something that lasts in style and condition. A shirt looks good for longer than a t-shirt even when both made from cotton.

When I dress well and put some time on it I feel better and confident. Great video. Cheers.

I enjoy your channel. I have had some big wins buying on eBay, and have also made some mistakes. That said, some of my favorite pieces are sourced from eBay either new/old stock or previously owned. The best thing you can do for eBay buying is KNOW YOUR MEASUREMENTS. Cannot be overstated.

Since I've stepped my game up, my old friends tend to pick on me. My work associates however, applaud. But, I've noticed some of my friends, quietly improving their style. One friend, who is in his 40s, still working as a bar back still loves his little jabs. But I enjoy a little confrontation, a little conflict.

Goodwill and Salvation Army has some amazing clothes sometimes!..NOS from Italy etc…tags still attached…Also…Burlington has clothes for around 1/3rd the price of Target..Kohls etc….and..they sell quite a bit of 100% cotton clothes,,which is getting very hard to get!….All their clothes are brand new…..

Can you do a video on fragrances? I have become addicted to colognes, I have some really good affordable fragrances but also ordered a bunch of samples from Parfums De Marly such as Oajan, Layton, Layton exclusif, Pegasus Exclusif, and carlisle. These bottles csn go as high as $400ish full retail but I can’t wait to smell the rich honey, vanilla, Smokey, woody and floral scents. You can’t overlook a good fragrance and how it makes you and the people around you feel…

Very true, every point.

Cost, especially shoes if you have problems with feet. Very few experts can provide the right thing in that situation. Otherwise, I agree with you. Keep up the good work.