100 Things That Happen To You When You Start Dressing Well

Dressing wellI'm walking out of a subway station the other day when this young lady (obviously a tourist) comes up to me and asks for directions.

I help her out, then I think:

“This happens to me a lot…”.

Is it because of the area (downtown, near the subway)? Or is it me?

The thing is, I was never the guy getting stopped for directions. No one ever used to ask me for help.

So why now? Do I look older? No. I look the same as I did in college, so that's not it.

Then it hit me. It's because I started dressing well. You see, when you dress well, you exude confidence. People, even strangers, pick up on this. In return, they give you respect, and trust goes hand in hand with respect.

When you dress well, you look like you have your act together. Imagine you're in a foreign city and totally lost. Who would you rather get directions from: a sharp dressed man or a sloppy guy in ill-fitting clothes?

Regardless of which person gives the best directions, the well dressed man clearly looks like he knows what's going on. After all, if you can't even get your clothes right, how can you be trusted with bigger things, like navigating a city?

I know this is kind of a random example, but there are lots of things that happen to you when you start dressing well. I reached out to some of my favorite stylish gents to see what happened to them when they decided to step up their style.

The response was overwhelming. So, in no particular order, here are 100 things that happen to you when you start dressing well:

1. Women check you out

2. Men check you out

Aaron Merino3. Cars stop to let you cross the street

You smile more!

~Aaron Marino

5. Strangers ask you for directions

6. Friends start asking you for style advice

7. Random people ask for style advice

8. Your boss let's you slide on that deadline

9. You get the job (even though it wasn't your best interview)

People bring you into their inner circle. They want to collaborate with you and be around you because they like the way you make them feel. You project confidence and goodwill.

~Kyle Ingham

11. People inherently trust you

12. Some people dislike you

13. People laugh at your jokes (even when they're not very funny)

14. Your friends make fun of you for being “metro” or even “gay”

15. Your friends start copying your style

16. You sometimes feel silly when experimenting with new looks

17. You notice style mistakes everywhere

At hotels, you sometimes get upgraded to a suite.

~Ryan Magin

19. You try hard not to judge people for making those mistakes

20. You give (and receive) that small nod of approval to other well-dressed men

21. People smile at you more

22. You detest clothes that don't fit

23. All of the sudden, half your wardrobe doesn't fit

24. You cringe when you see old pictures of yourself

You're not as impressed with other well dressed people.

~Alexander Zaytsev

26. You see collar gap all the time, everywhere (especially on celebrities)

27. You have mornings where you effortlessly just nail your outfit

28. There are days where you're late to work because you can't figure out what you want to wear

29. People compliment you regularly

Tanner Guzy30. You resist the urge to tell random strangers to get their pants hemmed

You expect more of yourself. Other people expect more of you.

~Tanner Guzy

32. You start to expect the occasional compliment

33. Women who never noticed you before notice you

34. You feel the urge to get (or stay) fit

35. Suits become comfortable

36. You acquire accessories (sunglasses, watches, belts)

37. You acquire more accessories (bags, ties, pocket squares)

38. Your apparel budget triples

39. Women mind less when they catch you checking them out

You notice the style details (good or bad) in everyone you see. You become an expert people watcher.

~Steve Mitchell

41. Men become jealous of you

42. People expect you to act like you dress

43. People expect you to be well spoken

44. Everyone says ‘hi' to you

45. You ask random men for advice on style forums

46. You critique outfits for random men on style forums

Antonio Centeno47. Acronyms like MFA, OCBD, DB, and MoP mean something to you

People assume you're the boss or work at high end establishments, they assume you have money, that you own the Lexus or Mercedes parked out front.

~Antonio Centeno

49. Older people assume the best about you

50. Superiors at work take you more seriously

51. Cabs always pick you up

52. You realize that going sockless can be delightful

53. You get comfortable with people looking at you

54. You give half your clothes away

55. Baristas and servers remember your name

Ryan Magin56. You start hating business casual (you'd much prefer just casual or dressy)

Bartenders serve you first.

~Ryan Magin

58. You stop wearing sneakers

59. Every time you wear loafers your friends say: “Oh, you're dressing up? Now I have to change!”

60. You're girlfriend becomes proud of you in a new way

61. You begin to understand the power of appearances

62. Shopping becomes sport

63. You constantly receive packages in the mail

64. You always have something that needs to be returned

65. You consider moving just to get more closet space

Andrew Snavely66. Your dry cleaning bill quadruples

It all starts to make sense. You can make smart, confident decisions about what goes with what. You start trusting yourself when something doesn't look right, and you know why.

~Andrew Snavely

68. You hate being underdressed

69. You overdress sometimes (but it's better than being underdressed)

70. You know your measurements

71. You understand why women love walk in closets

72. In meetings, people let you speak

73. The top drawer of your dresser fills up with buttons, collar stays, pins, sewing kits and cuff links

74. You start following style blogs…lots of style blogs

75. Sunday becomes wardrobe maintenance day (laundry, shoe shining, ironing)

If you're a young guy, people assume you're older. If you're an older guy, people assume you're younger.

~Tanner Guzy

77. Grooming becomes much more important

78. You experiment with different hairstyles

79. Women value your opinion about their style

80. You look forward to cold weather (layers!)

81. Packing becomes more difficult

82. You always want to dress appropriately for the occasion

Kyle Ingham83. You get your shoes shined

You inspire change in those around you. Your friends and colleagues see how confident and put-together you look, and it gives them a (positive) kick in the pants to up their game.

~Kyle Ingham

85. You get to know a cobbler

86. And a watch repairman

87. Outfits and hairdos that you assumed you couldn't pull off become viable options

88. You learn how to iron

89. You ditch your college jeans

90. You realize just how versatile a good pair of chinos is

91. Your wardrobe expands significantly

92. You long for a lean, versatile wardrobe

Your posture starts to change.

~Tanner Guzy

94. People assume you're wealthy

95. Cardigans and Henley shirts become wardrobe staples

96. You feel guilty when you hang a nice shirt on a cheap wire hanger

97. You acquire wooden hangers and shoe trees

You get noticed. People remember you as the guy who's ‘always dressed up'.

~Sven Raphael Schneider

99. You become happier

100. You keep pushing yourself, because it's a journey, not a destination

If you never thought dressing well could impact your life in so many different ways, it can. It's not easy, but it's definitely worth your while.

Have any of these happened to you? Got something to add? Leave a comment!

New Posts & Videos Every Week

Never miss a new post or video! Sign up for free updates, and I'll send you the "How to Dress Taller" guide for free.

No spam, ever. Unsubscribe anytime. Powered by ConvertKit


  1. Spot on!

  2. Damn

  3. How do you know me so well?!

  4. Great post. We study this topic all day everyday. Next gen will have to dress for a whole different type of success in the future. The competition out in the big, bad world is tough. Perception is reality.

  5. Excellent article and very true points. Thank you! I would also add that “your wife no longer needs to lay out your clothes so you’ll be dressed properly for events.”

  6. I thought I was well versed but could someone enlighten me on what MoP means?

  7. Excellent post

  8. I was out with my family having lunch the first time I got ‘the nod’. I just recently started classing up my look, moving from jeans and casual button ups up into ties and jackets. Another well dressed family came in, and they were all three immaculate. The father had a beautifully fitted casual suit, the mother in a very pretty dress, and their 3-4 year old son in crisp chinos and a tie. I happened to be looking their direction when he caught my eye, gave me a bit of a smile and a nod, which I returned. It felt great that such a well put together gentleman had noticed my style and approved!

  9. gregmora says:

    People ALWAYS ask me the time.

  10. Who is late for work because they cannot decide what to wear?
    A dapper man knows the night before and lays it out so he can just get dressed in the morning, even while chasing an infant and changing her diaper.

  11. You build a relationship with a tailor and spend way too much on alterations.

  12. I thought this was a fantastic read. I had to share with my friends and networks because I remember being a young guy and my grandfather explaining many of these points. For a while Men lost sight of being dressed for success and now it’s making a comeback. Nothing wrong with looking right and feeling great. I do it with my TieBros.com ties and I love seeing others on the same page

  13. Thanks for the tip. I always feel better about myself when dressed well and always looks for good advice to dress for success and be in good style.

  14. Great article – definitely worth the read!

  15. Oh man.. 100% true…. Great post

  16. Life is good!

  17. Emmanuel M'M says:

    Of these 100 things, I only relate to a few. At least this year my attitude towards dressing up (even though I still have not done enough shopping to consider it a makeover). We live, we learn, we do better

  18. Everything you stated in this, I have been through since I started dressing better. You are spot on. Great work.

  19. Great Post!! I have at least 50 of these things since I began dressing up nicer.

  20. Malaquias Alfaro says:

    Love it. I can relate to most

  21. On point!

  22. This is absolutely on point with everything!

  23. I thought I was the only one who this ever happened. Right on point !

  24. Barrie Osborne says:

    I have one gripe. It’s about guys who wear a sharp suit but dispense with a tie. To me a tie is an essential “accessory”. It can complement a suit; define you personality. A suit without a tie looks like the guy has dressed in a hurry and dispensed with the tie. OK, if the collar fit seems a little too tight, just undo the top button. No tie with a suit looks sloppy. It’s as bad as a guy wearing a casual with the top button done up,
    From Barrie (The Baz) Melbourne Australia and a Vietnam vet

  25. Hey! Any of you guys out there have the brainpower to address the above comment?
    It is a widespread trend here in Oz

  26. This is all so true.

  27. Patrick S. says:

    The life this list describes sounds like a never-ending nightmare that I wouldn’t wish on my worst enemy.

  28. I think 50 out of it all are things that I noticed. The article is so precise. Then If you’re a young guy, people assume you’re older. If you’re an older guy, people assume you’re younger.

    ~Tanner Guzy
    That’s just the greatest quote.

    Adding: You suddenly crave and want to teach a lot of people what you know about looking good through anyway you find

  29. Raven Solomon says:

    From a black perspective I’d like to add that this is a sweet little article. It’s the very tip of the Iceberg. For example… gaining free entry to clubs, invitations to events, great tables in restaurants and superb service, teenagers looking at you in admiration, people going out of their way to greet you, complimentary this and that whether it the grooming products or discounts at your favourite stores, upgrades on flights, that extra helpful cab driver who insists on carrying your bags, the oh so pretty ladies who wish to spend an evening with you, the guy who wonders if you might be gay… these and so much more are the everyday experiences of a well dressed, well mannered and well spoken brother.

  30. Well, I just have started reading on and applying some of fashion knowledge I have read on some style blogs such as this. It was awkward at first, thinking I could not pull it off as I wasn’t really a guy who’d fancy dressing up. I was just the jeans-shoes-plain shirt kind of guy, you could say. But when I tried one day being preppy, yeah a lot of people took notice and they were like, you look good today. Where did you get that sweater, it’s nice etc etc. It was a definite ego booster!

  31. Enoch Holmes says:

    Being a twenty-two-year-old, I feel I am… not entitled, precisely, but more like I can be allowed to get away with saying that young people my age, so-called ‘young men’, especially, can’t dress themselves worth a damn. Blackface is immature, Mark Zuckerberg looks like a teenager in jeans and performance fleece (The North Face, feh), and I often hear remarks that I look older than I am. My name is remembered when I drop by Starbucks. My girlfriend’s father, a rather dapper gentleman himself, frequently strikes up intelligent conversation with me and very clearly approves of my style. Even offered me a job a couple times. The folks at the Mid-Manhattan library all remember my name, and have recommendations for me. I dress (in my mind, at least) like I know what I’m doing.

    And I love it!

  32. Thomas Redding says:

    I find it odd that this website is called the modest man. This article was extremeley vain and egotistical. The constant claims that have no true backing or evidence are rediculous. But hey, keep telling yourselves that you are better than other people because of how much time and money you spend on clothes and it’s true… YOU will think YOU are better than other people.

  33. I think there are a lot of truths in what has been written. Certainly about feeling like you stand out. Since I opted to change my style for the better, although at first it made me self conscious, once I’d got through the embarrassment there isn’t a day goes by that I don’t receive a compliment. It’s nice to hear things like “you’re a stylish guy” and getting stopped in the street to be asked. I find people are more willing to enter into conversations with me.

  34. I was an average to above average dresser before but since I’ve started to take it up a notch I’ve noticed a lot of these things. When I try something on at a store I’m extremely picky already…this after having things tailored. This weekend I tried on a jacket that I really wanted to love. I ordered it to the store after doing an endless internet search. I get there and try it on. It is a small but it is way too long and just baggy. I figured maybe my tailor could fix it but it just wasn’t worth the effort. Then the guy finds another different one and tries to ‘sell’ me on how good it is and what a great deal. I had to walk away. Hard to do when you invest a lot of time to find something a bit unique.

    I’ve noticed many people looking at my shoes. I bought a nice pair of brown ones with cap toes and monk straps. I see guys and women check them out and then look me right in the eyes. I find my eye contact is much better with people because I feel good about how I carry myself so I have no issue looking strangers passing on the street right in the eye. Often it results in a smile which feels even better.

    It is work but it is work I enjoy. Thanks for this post. BTW, Aaron is fantastic. That’s how I found this site and many others that are so helpful.

  35. Carlossee' says:

    It seems that the negative comments which elude to ego and “feelings of superiority” are ill-placed, in this reader’s opinion. While everyone is entitled to an opinion, in America, one should educate one’s self on a given subject matter before making assumptions. Men have been so emasculated in the last 20 years to the degree that a lot of us walk on the “proverbial” eggshells of caution when we are out on the town. If dressing well is the therapy that a nation of men who, by the way, are often the offspring of the greatest generation (WWII vets), needs to once again feel like we can take charge of our success, happiness, appearance, and future endeavors, then so be it. It is about time we were given license to, once again, express ourselves through the trappings that once defined American men as the best dressed men in the world. Anyone that views such pride in appearance as an attempt to elevate ourselves (class wise, or in social status) above those less inclined to care enough to present themselves to the world as gentlemen and true contestants in this “game of life”, has missed the point in the tongue-in-cheek items peppered throughout this editorial. I IMMENSLY enjoyed the article and loads of the comments. B.t.w. I am a 54 year old, man of color born and based in Detroit, MI and I work and play around the globe at large. I have seen it ALL (for the most part) and no one does it like well-dressed, American men. I a going to make another reply post, in which, I will ad a quote that will inspire all to feel comfortable in their new found persona once they become the extraordinary gents into which we are transformed after we put on a suit of very fine clothes. Be well, gents. Stay thirsty!

  36. Carlossee' Santiago Oliva DeJesus Casanova Lumpkin says:

    As promised, I am including words for your consideration for those of us (both lofty and diminutive, in height) to consider when one feels embarrassed by the attention paid to one’s-self in our sartorial journey, and the nay-sayers who would have us go through our lives “blending in”. I submit that this be food for thought:

    Extraordinary men and women are extraordinary in everything they do. The lives of the ordinary are likewise and in every way common. It has nothing to do with wealth, fame, success, looks, race, birth, class, education etc. It has everything to do with being extraordinary or not.

    Before another extraordinary person can be intrigued by you, curious about you, desirous of you and covetous of you, she has to be able to see and recognize you. If you dress exactly like all the ordinaries, she will pass you by in a sweeping gaze that never fixes, that passes over the horizon of the ordinary, a never ending, flat Nebraska field. Dress is an extraordinary device. If you have the courage and style to stand out from the crowd, she will notice it. Then, if you have a twinkle in your eye and the wit to incite laughter, you will pass as many deliriously extraordinary moments as you are able to imagine. We all have the choice in life to be extraordinary or accept the fate of the ordinary.

    Choose to be extraordinary!

  37. That asking for directions part. I totally relate. Even in the mall someone asks me. Where is the supermarket? :))

  38. This list described my personal experience as being a well-dressed man in so many ways.

  39. I generally dress better than the average male in my small, Indiana town and even here experience quite of lot of these things. One day in the coffee shop a boy came over to me and said I looked “like a rich businessman.” I smiled and thanked him; it really made my day. I’m retired but still try to make the effort. It does pay off. I like these words from style god Nick Wooster: “To me, how you dress is a way to show you care. I think the way you dress is a direct reflection of what you will get out of your day; you make the effort, people will notice. You’ll feel better, and those around you will feel better.”

  40. Sanjeev Kalita says:

    Bang on!
    Every point is true 😀

  41. Where do I start? I always get so discouraged when I go into a store and nothing fits right. It makes me lose my motivation.

  42. One thing I have noticed is that coworkers swear in front of me less, and they apologize more if they do. If you dress nice you demonstrate from your appearance that you conduct yourself professionally, and oftentimes those around you try to match it.

  43. Abhir Mehta says:

    Oh my God! I’m 18 and this happened to me since I radically but upgraded my style after having studied menswear for a year. It gave me goosebumps in the most pleasant way.

Leave a Comment

Home · Free eBook · Start Here · About · Resources · Advertise · Contact