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
3. Cars stop to let you cross the street
You smile more!
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.
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.
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.
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
30. You resist the urge to tell random strangers to get their pants hemmed
You expect more of yourself. Other people expect more of you.
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.
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
47. 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.
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
56. You start hating business casual (you’d much prefer just casual or dressy)
Bartenders serve you first.
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
66. 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.
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.
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
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.
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.
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’.
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!