How To Dress Up When Others Don't

How To Dress Up When Others Don’t

If you like classic style, wanting to dress up when others don’t happen to you all the time.  Here are some helpful tips on how to deal with people who question you about the way you dress.

Recently, the viewer Amir left a comment on our video, Things I Get the Most Compliments On.

“Raphael, I’ve been upgrading my style. I used to wear graphic tees, ripped jeans, and sneakers and now, I wear untucked casual button-ups, dark wash jeans, or chinos, and chukka boots. However, I still don’t feel satisfied with my current style. The thing is that people around here never dress up. Is there anything wrong with dressing up all the time even to the most casual of occasions? I’m really scared of this step.”;

Amir, I can totally sympathize with you. You want to dress up and put your best foot forward yet there are others who question your motives and may even be vocal towards you about it. I’m often the most dressed up person in a room and it inevitably will catch some attention. People ask me what the occasion is and I just say “It’s Tuesday!” simply because that’s the way I like to dress.

Recently my wife and I went out for dinner in a new hip restaurant in town and of course, we wear nice clothes. So the waiter asked, “Oh, where are you headed?” and we just said, “Here!” And she was really surprised because otherwise, people just don’t dress up as much just to go out for dinner.

Wearing a suit evokes discipline, power, self-respect and respect from other people around you.

Wearing a suit evokes discipline, power, self-respect, and respect from other people around you.

Dressing up will always make you stand out and it really pays to know how to deal with the positive aspects as well as the negative ones. If you haven’t already done so, I suggest you watch the 101 Things That Change When You Dress Up because we cover mostly positive things but also some negative ones.

The paradox of style is that many people care about it for different reasons. Usually, it falls within a spectrum of people dressing for themselves or people dressing purely for others. In any case, clothes and accessories are something you wear directly in your body and because of that, it immediately becomes part of your visual identity.

One of the many negative comments from our videos

One of the many negative comments from our videos

Am I Dressing For Myself Or Do I Dress To Impress Others?

Being inappropriately attired can be a form of disrespect or it can be seen as a cry for attention. At the same time, dressing to fit in can mean that you’re indifferent about your outward appearance or that you simply want to be invisible to a group of many.

If you want to dress up – Do it, enjoy it and own it! There’s really nothing wrong with it and I’ve been doing it for over 20 years and the benefits far outweigh the negatives. Yes, there will always be someone who has to say something negative about you or the way you dress but you just have to deal with it. Some of them may feel threatened when they judge you or they elevate themselves above you and think they’re superior to you.

Just look at YouTube comments for example. No matter what I or anyone else produce, there will always be someone who has something really negative to say about your approach and how you do it. At the same time, they don’t go out and produce a better video, they just criticize you. Rather than being impacted by the haters, I focus on the comments of the people with constructive criticism, questions, or simple observations so we can do videos like this. So all this may be easier said than done.

How Do You Cope With Issues That Arise From Dressing Well?

Suit for Weddings, Cocktail Parties & Events

Suit for Weddings, Cocktail Parties & Events

1.  Whenever You Dress, Consider Appropriateness.

For example, at a wedding, you never want to out-dress the bride and the groom because it’s their day. At the same time, if you go to a funeral, a burgundy or red flannel suit will simply detract from the event and it would be inappropriate. When there’s a dress code indicated such as cocktail attire, you should not wear black tie because that would be obviously overdressed.

2. If There Isn’t A Dress Code, Consider Flexibility.

For example, when you’re on a plane, you see people wearing sweatpants or a suit, so whatever you feel comfortable with works.

Examples Of Business Casual Dress For Men Throughout Casual Dress

On the other hand, if you’re in a business meeting and you’re not the boss, the dress code can be pretty much stipulated without being written down. In that case, consider the company culture. There’s nothing worse than wearing a three-piece suit in a startup company that simply wears jeans and t-shirts all the time. It makes you look odd and stand out in a weird way.

If you’re in a social event with friends, you should truly be able to wear whatever you want and whatever you are comfortable with and whatever you’re supported by. If it’s a more casual outing, it’s okay to be more casual.

Reversible Harrington Jacket in Navy and Madras Pattern

Reversible Harrington Jacket in Navy and Madras Pattern

3. Dress To Please Yourself.

Think of dressing as your hobby and it’s something that you enjoy. It’s about you and what you like to do, not about others.

Deflecting a compliment is clearly insincere

Deflecting a compliment is clearly insincere

4. Learn How To Accept A Compliment Graciously So As Not To come Off Arrogant.

When you dress up more, compliments will be coming your way so it is best to be aware of how you should react when a compliment is thrown at you.

5. Have A Comeback Ready.

If you’re asked why you’re dressed up, have a few answers prepared that you can give right away so you don’t have to engage in lengthy conversations. Shut the conversation down and simply go about your way.

By having an appropriate comeback, you exude confidence. Other people will just leave it at that and won’t bother you again. It’s important that a response should never be defensive or mean. Saying things like because “I’m not a peasant” or “I wasn’t raised by wolves” will always be kind of offensive to people and it automatically reflects on them which will just draw you into a long argument and it’s just a pain. That aside, as a gentleman, you never go down under a level.

Ideally, you shouldn’t go down the rabbit hole of explaining. It’s the same politics if you start explaining, you’re losing. Aggressive or negative people want to engage you in a fight, want to drag you down to their level, and then they beat you with experience so don’t do that. The best comebacks are short and sweet.

Comment: “What did you dress up for today?”
Comeback: “It’s Thursday!” Or if you want to be snarky, you could say something like “Adulthood.” But again that may be seen as offensive.

Comment: “Why do you look so fancy?”
Comeback: “Why not?”

Comment: “Why are you so well-dressed?”
Comeback: “Because I know how to.”

Comment: “Do you think you’re better than us?”
Comeback: “No, dressing up is just my hobby.”

The sooner you’ll accept that judgment will always be around, the easier it gets to focus on what you truly want.

Agnelli confidently wearing his watch this way - never cares what people thinks about it

Agnelli confidently wearing his watch this way – never cares what people think about it

6. Do Not Care What Others Think Of You.

Personally, I’d say it comes very naturally to me and being on YouTube and being exposed and having that negativity around me just helped me to develop an even thicker skin. There’s a good saying along the lines of “What other people think of you is none of your business” and I pretty much agree with that. People-pleasing, approval addiction, or the fear of rejection, will always be in the way of what you truly want for yourself. If you care a lot what other people think of you, you may want to look into the book, The Subtle Art Of Not Giving A Fuck.

Sven Raphael Schneider wearing Atelier Eyewear Acetate Sunglasses

Sven Raphael Schneider wearing Atelier Eyewear Acetate Sunglasses

7. Be Authentic, Be You!

Authenticity provides you with confidence. People who are confident are perceived in a much different way. Fewer people will want to argue with you and they will accept you for who you are.

How do you deal with negative remarks about being well-dressed? Do not hesitate to share your thoughts below!

How To Dress Up When Others Don't
Article Name
How To Dress Up When Others Don't
Tips on dealing with people who do not seem to appreciate your style, the way you dress up, and how you carry yourself.
Gentleman's Gazette LLC
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65 replies
  1. Bill Yeats says:

    I am disappointed to find that culture has been given a miss again. If I might point you toward a topic for literary discussion, I well remember as a boy reading William Brown’s Schooldays which concerned young Brown’s time as a boarder at Rugby where he was befriended by Harry East and had a lot of trouble with Flashman. In the version available free of charge on the YouTube which you so admire, young Brown lives at home with a sister and a brother, Harry is known very formally as Henry, and a female neighbour has been introduced to take the place of Flashman. Frankly, I cannot feel that the alterations improve the story but will treasure your opinion.

    • Tim says:

      Not wishing to be pedantic, but I think you’re referring to “Tom Brown’s Schooldays”. Flashman was a nasty piece of work.

  2. Chic says:

    Great article. Dressing well helps me exude confidence and feel amazing. It’s so unfortunate that the art of dressing is fading away in corporate America and many social circles.

  3. William Mandelbaum says:

    My response to “why dressed up?” I tell them “Because I knew you were going to be here and wanted to show the property respect!” Bullshit? Yep. Effective and we’ll received? Always!

    • HKB says:

      If I know the person reasonably well, I sometimes reply to the above question or similar comment with “I knew I was going to meet an important person like you today.” I do this in a slightly facetious way with a smile so they know that I am making a point but not rudely.

      Showing respect for others when in their company is a reason for dressing appropriately for the occasion. Some may not appreciate that, but that is their problem. Others may follow your example. I am appalled at what some persons wear in church. It behooves the leadership to set an example.

  4. Dan O. says:

    Really enjoyed the article. Whenever I get the question, “Why so dressed up?” I usually reply, “Look good, feel good!”. It has worked very well for me so far. Keep up the great work Sven!

  5. Terry says:

    Great article on a common experience for most of us. I have several retired (or not) acquaintances who boast that “I haven’t worn a tie for (fill in the time).” I respect their choice, but on some occasions am thinking “I believe It!”

  6. Steve says:

    Dressing-up is new for me…coming from working in Rock N Roll and being a motorcyclist, I have spent most of my life dressing down but, as I progress through my 50’s, rather suddenly, I am enjoying ties and suits in a way that I never did. Event hats are a thing with me now (Not caps). For the holidays I went to my wife’s side of the family – I wore black jeans, dress shirt, tie (with clip) and a sport coat along with a long overcoat. My wife asked me why I’m “all dressed up?”. I answered, “We’re going to see your family, it only seems right.” she really couldn’t argue with me but reminded me they’ll all be in jeans and tee shirts. In the end I received lots of compliments and didn’t feel out of place.

  7. David says:

    Very good article.However, I must say that I do not agree with your comment “There’s nothing worse than wearing a three-piece suit in a startup company that simply wears jeans and t-shirts all the time. It makes you look odd and stand out in a weird way.” If they are a business organization, they have no right to wear jeans and t-shirts. They should be dressed properly. If one wears proper attire at such a company…then then the slobs in the jeans should bring themslves up to the higher level, not the other way around. There is no excuse for a business executive, in any company, to be dressed as something that the cat dragged out of the sewer. Quite frankly..the only time I’ve ever worn jeans was to shovel manure in my horse barn.

    • Sean says:

      Jeans and a hoodie or a t-shirt IS the appropriate dress code in almost all San Francisco Bay Area start ups. Dressing well, unfortunately, can actually dramatically harm your career here if you do so. Of course, there are little things you can do, but for the most part, no one is going “see the light” by your example – you’ll just look like an idiot as the author suggests. The fine art of dressing, is always knowing what you can get away with and staying within the realms of the appropriate at any given situation.

      • David Kalil says:

        Sean: I read with interest your post. If our country has dengerated to such depths that dressing well can harm a career, the may the Lord help this country. I don’t know anything about San Francisco and after reading what you said about the sloppy attitudes there, I have no desire to go there. Perhaps those people in San Francisco should wake up ..and learn from how businessmen dress in Boston, New York, London, Naples. Palermo..etc. As a matter of fact…at Harrod’s in London, a some of the finer men’s stores in Naples and Palermo…stc…it has always been the policy that if a customer was dressed inappropriately, the doorman refuses him entrance into the store. San Francisco “gentlemen” need to drag themselves up from the gutter.

        • Mike M says:

          I have to agree with Sean. Specifically in the tech industry, if you come to work in a suit, it’s usually assumed that you are secretly going to an interview. If you say otherwise, it’s assumed that you’re lying. Then you’re branded as a liar and an employee that has little interest in working at the company and is trying to find a way out.

  8. Robert H. Howerton says:

    I join Mr. Mandelbaum. I give the happiest, most natural look with the biggest, but natural smile, and say, “I dressed just for you.” I might say that to five people, but I don’t care. In fact, largely it is true. However, it just is natural to me. Whatever you do or say, enjoy life and let others know, in a manner that is natural to you, that you are glad to see them. If what you do is forced, they will detect it and be of the opinion that you are a phony and your clothes do not fit even if they have been meticulously tailored by the best tailor in the world.

  9. rico says:

    A gentleman dresses appropriately for all occasions. If a person asks if a well dressed man is “trying to make us look bad” it is an attempt to insult and alienate the gentleman in question. A chuckle and a head shake “no” is all you need, just walk on

    Remember not all insults demand an answer. Smile and walk on. On the other hand I’ve been asked if I felt hot in a suit. I used the opportunity to educate the questioner on using natural fibers and practicing good dress habits.

    A gentleman need not suffer fools.

    • Dave says:

      Rico …Absolutely correct.!!! My humble opinion is that Mr. Sven is approaching the subjuct from the subject from the wrong perspective…that of weakness. . Slobs in jeans have no right criticizing a well-dressed person. It is they who should be humiliated, not the rest of us. The best defense is a good offense! Water seeks its own level….let the garbage in jeans seek its level. ..instead of denigrsting well-dressed people…they should seek out locations where they can be comfortable…i.e. with other slobs of their own ilk.

  10. Chris says:

    This is a very interesting subject, and you’ve handled it well. I only discovered the world of men’s fashion about six months ago (thanks entirely to your videos and articles, Raphael), and this has been an interesting side effect – people wondering why I’m wearing a pocket square, or whatever. I think when people I ask, my favorite response is, “I just love classic men’s fashion.”

  11. Stephen Clay McGehee says:

    Inappropriateness in dress can have very real consequences. I once interviewed a candidate for an engineering job. He was knowledgeable, eloquent, and personable – pretty much what we wanted, yet he did not get past that first interview. My reason? He showed up dressed in a western-style shirt, cowboy boots, and a western-style hat. He was neat and clean, nothing sloppy at all; however, it was inappropriate for a white collar job interview. That indicated a lack of good judgement to me, so he was rejected. Don’t be “that guy”.

  12. Eric Ericson says:

    Great article! I’ve always “dressed up” wherever I’ve gone. I used to work for the airlines and it was a rule to dress up wherever you went to make sure you gave the right impression. Now no one dresses up. I’ve found though that I get more compliments than negative comments, and to be honest, helped during the good old days when I was dating. In fact, one of the reasons I was able to convince my wife to marry me was that she was impressed with my fashion style. I’ve always found that a blazer, button down oxford shirt and beige slacks go well in any situation.

  13. David Kalil says:

    Rico …Absolutely correct.!!! My humble opinion is that Mr. Sven is approaching the subjuct from the subject from the wrong perspective…that of weakness. . Slobs in jeans have no right criticizing a well-dressed person. It is they who should be humiliated, not the rest of us. The best defense is a good offense! Water seeks its own level….let the garbage in jeans seek its level. ..instead of denigrsting well-dressed people…they should seek out locations where they can be comfortable…i.e. with other slobs of their own ilk.

  14. Bill Donaldson says:

    If this issue pops up, I say “When I worked, I had to dress grungy because the job would get dirty. Now that I’m retired, I thought it would be fun to try something different for a change.”

  15. Mark says:

    There is a saying in the military that artillarymen lend dignity to an otherwise vulgar brawl. I keep that in mind. When people comment I generally respond with some version of noting that I interact with of people and need to represent my office well. But I like the response “For you!”

  16. John Clapperton says:

    Good suggestions above. My favourite comebacks, depending on circumstance and/or how well you know the person, of course:

    “This IS the [name of establishment].”
    “Well somebody has to.”
    “Just trying to raise the tone of the place.”
    “Well it gives you something to talk about.”

  17. Andrew Gregg says:

    In my past professional life, I consciously strove to be the best-dressed man in the room.

    Neither handsome not athletic, dressing well was my edge.

    Peers were sometimes amused, superiors were complimentary, and occasionally, colleagues asked for my advice.

    When accosted straight up about my elevated formality, I responded, “I am showing respect for our work.”

    In so doing, a neutral reference indicated my regard for our transactions in a way that did not insult a sloppy colleague.


    Andrew Gregg,
    Palm Springs, CA

  18. Steve says:

    When people comment on How well dressed I am (their words) I always reply ” I’m old (72) and I want to be a well dressed corpse”.

  19. John Greyson says:

    I often respond with “Well, someone’s gotta class up this joint.” And really not give a crap what they think. Amen.

  20. Bill Dickman says:

    When I get a compliment on my attire I simply say “Thank you” or “I appreciate that” and shut up. If there is a comment/question on my “dressed up look”, I reply “just trying to look my age”, “makes me feel good”.

  21. Michael says:

    It is refreshing to read how dressing in an historically ‘up’ fashion is what makes many of us feel better. Damn the rest that live only in yesterday’s designer jeans and a t-shirt with a message. Sean, respectfully, is worried about protecting San Francisco’s style, ( a place where people don’t think using a toilet is fashionable) ….please spare me while I adjust my tie. If I’ve had to dress ‘like this’ all my life since prep school days, so be it. In fact this tie has been stylish since ‘you’ were born.

  22. Mike says:

    I always take the time to look my best and dress probably to the edge of overdressed for whatever occasion. It’s my hobby and I have dressed as such since childhood. I had never thought of this until a young lady whom my wife and I see often on our what we call “Sunday Funday”. Basically brunch then a late lunch and a few cocktails. She made the comment to us that” I must put a lot of pressure on my wife of 30 years. That i’m always so impeccably dressed”. I told her that I have no intent of that and dressing is just what I do. My hobby. I have thought about her question quite a bit since although I haven’t dialed it back at all. And do not intend on it! 😉

  23. Veda says:

    I remember the old days when criticism wasn’t allowed on Gentleman’s Gazette FB and I was wondering why a GG customer such as myself was being argued. So I see this as a sign of maturity. Good job. Back on topic, dressing well doesn’t mean formally dressed. You can dress well in informal clothes with hood ala GQ or even mix street with sartorial. It’s never about your opinion but about the beholder’s. If you think you’re dressing well but not well received by the surroundings then you just expensively failed.

  24. Oscar says:

    I completely agree ! People not dressing well have no right to have a say about people dressing well. It has no logic. I really don´t want to offend anybody, but those people having bad comments on a well dressed person, seem stupid to me without much intelligence. The world can be glad, that there are still people guarding old traditions and beautiful things. We should support positive aspects of life, not negative ones. If someone want´s to be a slob, so be it, but don´t dare to stick your nose into someone else´s business. People behaving like that, are the most arrogant creatures. Thank you for this article Mr. Schneider and keep making new ones.

  25. Tim Cogswell says:

    Interesting topic. In my experience, women usually offer compliments when men are well dressed (perhaps a clue for men who feel that being well dressed is unimportant). Men, on the other hand, often look confused as if they are missing something. Some are snarky, as if being well dressed is an effort to prove something. If asked, I usually say, “It’s what I like” and move on or change the subject. I figure, if they don’t ‘get it’, to offer any explanation is likely a waste of time anyway.

  26. Jim Barone says:

    My response? “I’m bringing sexy back.” That usually ends it. If a snarky comment follows, I’ll look the person up and down and say something like, “Do you really expect me to take sartorial cues from you?” Or, “Are you the expert?” It almost never goes farther than that. I know this isn’t very gentlemanly but I believe I’ve perfected the art of not giving a fuck.

  27. otgh says:

    Great article and very incisive. One caveat though….usually Sundays I don’t sense that people have an issue with being suited up (they usually surmise that you are attending church service and are wearing your Sunday go to meeting outfit). Now on a Saturday, that’s when I find the most questioning of my attire. I dated a young woman years ago, and she requested that I not be so dressed up every time we went out. She said while she appreciated the look, it made her feel self-conscientious that she wasn’t dressed to match.

    • Oscar says:

      I know, what you mean. Well, it´s her problem, not yours. If a woman tries to change you to her way, then it is a manipulation and low self-esteem. I would send her away from me that very second she tries to pull this out on me. Upgrading the style makes sense, not downgrading. Never follow anyone on lower level ! Be smart and let the sheep live their fake lifes. Well not every sheep is fake in the world, but it seems like most are to me. I hate those people hiding their bad character. Have a nice day !

  28. Joel C Johnson says:

    Always enjoy your reassuring me that I was right. Started working into formal country and western attire and find the short silk ties of the second world war I inherited from grandad make great dress up with elaborately decorated western shirts when I don’t want to where a bolo tie. Being from SoCal ,and exposed to a lot of clothing variation growing up, I am open to more striking mixing and matching than you seem to be, but enjoy your patterning and color coordination . Took up dancing Argentine tango and found a swallow tail cut away that fit me at a thrift store. Have never had a woman say no when I asked them to dance wearing that outfit. Clothes definitely make the man, (or person). Here in the great N W T-shirts and ski parkas are formal wear so thrift shopping for high fashion is great sport and bargains galore. I refer friends who ask about fashion help to your blog, Myself I even make my own clothes just to get what I want and unique. I wouldn’t be an award winning artist if I listened to everybody else! Keep up the good work!

  29. Murray Mac says:

    I simply reply because I have to wear a horrendous work uniform (provided for safety reasons) the other 5 day’s of the week. Being smartly dressed helps me relax, I oddly associate it with time off.

  30. Robert says:

    My response is as varied as my dress. I’ve used, “I work outdoors and can get dirty, so when I’m not in my work clothes I like to dress nice”. I’ve also used, “I’m fat and bald and my wife is gorgeous so I need all the help I can get”! I don’t care what people say, everyone has there own opinions, problems and issues, as for me, a response in order to belittle or embarrass them is in just as poor taste because now my positive attitude has turned negative. “To thine own self be true”.

  31. Robert says:

    Negativity, such negativity. We must calm our tempers, dwell on a higher plane, let us not be a wolf in sheep clothing. As we stand before the mirror each day remember, we’re not Gentleman because we dress nice, we dress nice because we’re Gentleman!

  32. Kingston Lim says:

    In order to not appear to be “overdressed”, I would say the easiest way would be to not appear “over dressed” I would say the simplest way would be to wear something that can be dressed up or down. A buttoned shirt and blazer is one example. You can keep a tie in the office to dress it up or remove the tie and blazer while rolling up your sleeves to dress it down.

  33. Simon says:

    I love the blue stripe boating blazer you wore in the video. And there’s pants to match? Can you post a photo of the whole suit somewhere please. A bold look but I think you could pull it off Sven.

  34. JH says:

    I was recently mistaken for an undertaker at a funeral home. The woman apologized and stated, “you look so nice, I thought you were one of the staff.” That was nice.

    I have not received any negative comments, but then again, I am slightly odd and everyone knows it, so they are not surprised that I am slightly out step with the rest of the world.

    I even had a young man pass me on the street in Baltimore, smile and say, “lookin’ sharp, big man!”

    I just smile and thank them. If they ask why I am so well dressed, I tell them that it is just something fun to do.

  35. David Kalil says:

    If others don’t have the dignity and aplomb to dress properly…while some of us do so, then it is their problem, not ours. Enough with how it is acceptable for a the technology industry..or whatever field of endeavor. It is not acceptable..absoluitely not. They simply show their lack of good breeding, period. Let’s stop making excuses to justify sloppiness and bad taste.

  36. David Kalil says:

    If others don’t have the dignity and aplomb to dress properly…while some of us do so, then it is their problem, not ours.

  37. Prasad says:

    To Amir,

    Sven has put it so aptly. Indeed, it comes a surprise that people find it offensive when a person is properly attired, especially when there is nothing overdone. No man / woman who coniders herself worth will have any objection to someone who is well dressed. The wholesome agreeable aspect, as put by Sven, is that when you are appropriately dressed, you are respecting your host and keeping up his regards and honour. I don’t see any way a well dressed person offending the host’s sensibilities.
    That leaves the question about ‘others’. Again, as has been rightly said, leave the others to rest. Perhaps, it is the confidence exuded by a well dressed person that brings out the lack of poise in naysayers. Self respecting people nave no qualms acknoledging a well dressed person for his attire.

  38. Joris says:

    This one only works on Fridays:
    When asked why you dressed up today, just reply ‘because it’s Casual Friday’.

  39. Rob powell says:

    If you make a habit of it your acquaintances eventually won’t even notice. On tv show ” how I met your mother” Barney was always well dressed and everyone else was tee shirts and jeans. After awhile you don’t even notice

  40. Jason Gould says:

    I get lots of comments on how I dress (usually 3 piece suit), I accept the compliments graciously and just say thanks or I appreciate it. I have never really had any negative comments. Thanks for a great post.


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