100 Things That Happen To You When You Start Dressing Well

Dressing wellI was walking out the subway the other day when this young lady (obviously a tourist) came up to me and asked me for directions.

After helping her out, I stopped and thought:

“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 can’t be 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!

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