101 Things That Change When You Dress Up

101 Things That Change When You Upgrade Your Wardrobe & Improve Your Style

Often I meet men who tell me that they are comfortable in the clothes they wear, even though they admit that they don’t look good in them. Most of them don’t see the benefit in dressing up and so they just wear cargo pants, flip flops, and T-shirts.

Most men don’t realize that they could probably earn more money, attract more attention from potential partners, and be taken more seriously if they dressed well. Of course, dressing is a process and it takes some time, but at the end of the day, it is always worth it. When I was growing up, my personal style was not developed at all — my parents didn’t care too much about clothing — and so I just wore whatever I had without any concern for style. At the age of 14 and 15 I started to develop an interest in style, but it wasn’t an overnight success. Especially in the beginning, I had to try out some things before I found the style I really liked. Over the years, I have noticed a number of changes that happened after I began dressing well and improved my style. In this article, I would like to highlight 101 things that will likely change for you if you dress better.

Before we start though, I want to share a “before” photo when I dressed poorly and an “after” that represents my style now. It’s a world of a difference — but what I want to show you is that any man can make the decision to dress better. Will you master the art of clothing in a few days, weeks or months? Unlikely — but you will continuously improve and after a while you’ll feel uncomfortable look at “before” pictures of yourself because you have come such a long way.

Before, I was wearing short sleeved shirts in black with designer pockets, white pants and square-toed shoes, a leather jacket with gaping collar and a horrible printed silk tie along with with a cheap straw hats and equally cheap belts.


A few years later, I wore a stroller suit that fit me well and even a white tie ensemble. I know you can change your style too, and I am sure many good things will happen to you because of it.

101 Things That Change When You Upgrade Your Wardrobe & Improve Your Style

1. Coworkers ask you more questions and take you more seriously

2. When you walk on the street, men will observe you

3. Wherever you are, women notice you

4. People on the street ask you for directions because you look trustworthy

5. You will have no problem test driving a Porsche or Maserati

6. Strangers will compliment your style

7. Your guy friends may make fun of you in the beginning, but soon they will solicit style advice

8. Good friends ask you to help them order a suit and ask you for color combinations

9. People smile at you more often

10. At the bank, you don’t have to wait very long anymore

11. You are more likely to receive an unexpected upgrade  — in a hotel, at the car rental desk or for a better table at a restaurant

12. If your superiors are sloppy, they may feel threatened

13. People assume you are successful and treat you better

14. Sales people are more likely to talk to you — but they are also more likely to leave you alone if you tell them you are not interested

15. Friends that usually just wore t-shirts all of a sudden wear a blazer when they meet you for dinner

16. You begin to want mother of pearl buttons on your shirts and horn or corozo buttons on your jacket; additionally, you want your buttons to have a shank, so they button more beautifully

17. You want to learn more about style and sign up to our newsletter

18. You notice little details such as a hand-sewn buttonholes or the last of shoes other men are wearing

19. You will likely start to notice others’ (poor) style choices,  poor fit, etc. – always remember that you might have committed some style mistakes as well when you started!

20. Some people at work may dislike you because you are dressed better than them

21. Some may think you are more arrogant, but if you are friendly you can quickly show them otherwise

22. Moths become your enemy

23. Suits and shirts that you always thought fit properly suddenly feel like an ill-fitting potato sack 

24. You become interested in closets and their size

Voxsartoria's Shoe Closet

Voxsartoria’s Shoe Closet

25. You analyze other people’s style and you smile when you see them wearing a real ancient madder silk tie, peccary gloves or double sided scarves

26. You realize your body is asymmetrical – your right shoulder is a tad lower than your left one, and your right thigh is slimmer than your left…

27. You start to see the scourge of oversized jacket armholes everywhere

28. You start wearing a tie to work

29. You will iron shirts better than your mother

30. You buy your first knit tie

31. Compliments from people who don’t dress well themselves mean less to you

32. Your alterations tailor knows you by your first name, and you know where to get hats reblocked

33. You don’t want to leave the house without a pocket square in your jacket

34. You understand the difference between a full canvas and a half canvas jacket

35. When you travel, you always look for nice haberdasheries or men’s accessories stores

36. You realize that your suit or jacket looks very different with a few new accessories

37. You buy more accessories and get rid of the shiny $5 silk ties you had since you were a teenager

38. Materials become important to you and you check if a sweater is made of wool or blended with polyester

39. Women are more likely to flirt with you

40. You take a closer look at your dry cleaner, washing machine, iron and ironing board because you don’t want to ruin your investment pieces

41. You realize sunglasses are not just functional but that different kinds work better with certain outfits than others

42. When people see you in gym clothes they are surprised

43. People will argue less frequently with you and you will achieve your goals in discussions more easily

44. Acquaintances are more likely to invite you to parties

45. The name Alan Flusser means something to you

46. You start reading blogs, websites and magazines about men’s clothing style

47. GQ, Esquire etc.  become superficial and you realize they are not worth your time anymore

48. Things like 6×1 DB, MoP and Scye mean something to you

49. People want to take selfies with you

50. Co-workers and superiors compliment you on your presentations at work

Mid brown monk strap shoe with green socks and classic prince of wales suit

Mid-brown monk strap shoe with green socks and classic prince of wales suit

51. You don’t wear tennis socks anymore and invest in over the calf socks and become a little more daring with sock colors

52. You consider going sockless with loafers in the summer

53. You try to match the color of your belt and shoes, and your shoes now need shoe trees

54. You think about getting a pair of suspenders

55. People remember you as the stylish guy even though they have only met you once

56. You don’t want to take your jacket off anymore

57. Flip Flops are a thing of the past (or at least exclusively for the beach or sauna)

58. You get rid of your brightly-colored shirts and invest instead in pastel tones

59. You say goodbye to square toed shoes and you try to understand the difference between Blake, Blake Rapid and Goodyear Welting.

Black Cap Toe Oxford from the Deco Line of Gaziano & Girling - Note the V-Opening that should close upon break-in of the shoes

Black Cap Toe Oxford from the Deco Line of Gaziano & Girling – Note the V-Opening that should close upon break-in of the shoes

60. Your new suit gives you a V-shape as if you had worked out 5 times a week at the gym

61. You begin to understand the power of appearance

62. Matching colors and patterns in an interesting way becomes your new sport

63. Your standards get higher and higher and you don’t need a salesperson anymore when it comes to shopping for clothes — you are less likely to get sucked into “good deals” if the fit is not right

64. Your dry cleaner knows who you are and gives you a volume discount

65.  People who knew you as a child or teenager comment favorably on your Facebook photos

66. You only use shoe horns to put on shoes and shoe shining becomes very important

Fort Belvedere Shoe Horns

Fort Belvedere Shoe Horns

67. You sometimes get overambitious — thus creating a look that is not your best, but you know you can only improve your style if you constantly challenge the status quo

68. You don’t mind being overdressed

69. You have a spreadsheet with your measurements so you are always prepared

70. You want to visit Rubinacci in Naples, Caraceni in Milan, and Savile Row in London

71. You need to reorganize your clothes storage space — and you now want shoe racks

72. People assume you have more authority and will interrupt you less frequently

73. The meaning of “casual” dress is now redefined as an odd combination

74. You start to have a monthly clothing and accessories budget

75. You buy an unusual suit on sale, because the fabric is so great and it is all handmade — but then you realize the fit is not so good and you return it

76. You don’t trust the dry cleaner with your precious shirts, so you wash them on delicate in mesh bags so you won’t fray the collars

77. You start to become interested in other stylish things like watches, whisky and shaving with an old school razor.

78. The black suit you bought when you had no clue is now only used for funerals

79. You start to dislike monochromatic looks

80. You look forward to cold winters so you can wear your heavy overcoat, gloves, and scarves

81.When you travel you always take your biggest suitcase to avoid squishing your suits

82. At the airport you have to explain the TSA agents what metal collar stays, collar pins and tie pins are

83. You want shoes with leather soles, not rubber

84. You develop an affinity to tweed and other fabrics with a depth of color

85. You don’t throw away your shoes anymore, instead you have them resoled at the factory or at a local cobbler

86. You develop an interest in cuff links and French cuff shirts

87. You try to come up with different hairstyles and grow a beard

88. All of a sudden you don’t like those glasses you’ve had for years, and now you want a stylish pair of acetate or horn frames

89. You throw out your college hoodies

90. You invest in a pair of brown suede shoes

91. You realize one can never have enough ties

92. You invest in a tuxedo and seek out Black tie events

93. The wire hangers you get from the dry cleaners become unacceptable and you upgrade to fine suit hangers with a wide shoulder pad for your jackets and suits

Hanger Project (Made by Beverly Hangers) vs. Butler Luxury

Hanger Project (Made by Beverly Hangers) vs. Butler Luxury

94. You start wearing bow ties, and you always want to tie your own

95. You freak out when you find a vintage silk top hat in your size

96. You aren’t afraid to invest in your wardrobe; you know that a $450 pair of black cap toe oxfords will last for years

97.  Your significant other has to wait for you to leave the house

98. You enjoy seeing yourself in the mirror, you get more confident, and you express that in everything you do – and other people notice it

99. You get excited if the dress code is Formal Friday and you dislike Business Casual

100. You start hanging up your jackets in the car because keeping them on when you drive wrinkles them

101. Scientific studies have shown that stylish clothes make you more attractive — and attractive people earn $250,000 more than a less attractive counterpart – so dress better and earn more.


102. When you are standing in front of a judge or a jury, the decision is more likely to go your way.

What are the things that changed for you when you dressed up? Please leave a comment below!

101 Things That Change When You Upgrade Your Wardrobe & Improve Your Style
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101 Things That Change When You Upgrade Your Wardrobe & Improve Your Style
Explore the 101 things that could change in your live if you would unlock your full style potential by dressing better + before & after pics
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  1. James B. says:

    Great article! Here’s a true story. For most of my life the highest pinnacle of sartorial elegance to which I aspired was tatty jeans and an oversize lumberjack shirt. Then a while ago I came across this website by accident and something connected. I think I had known for a while that the way I dressed probably wasn’t doing my business any good, and it gave me the push I needed to start making some changes. So I bought a few nice clothes which I tried on at home, but for some weeks they felt so alien and ‘not me’ that I couldn’t bring myself to wear them outside the house.

    Finally I plucked up the courage, got dressed up and went for a walk around town. It was a Saturday, and it was heaving with people. I don’t think I’ve ever felt so awkward or out of place in my life, I felt a total fraud, an imposter, and was sure that everyone must be laughing at me. Then it started to rain, and I didn’t have an umbrella, and I was wearing these rather nice chelsea boots for the first time and, being a neophyte, I had not scrubbed the soles before wearing them and—well you can guess what happened—I slipped and fell: not just a little trip, but a monumentally impressive flailing crash onto my backside.

    So I lay there, hardly able to move and genuinely wishing I was dead, when I found a woman leaning over me with a concerned look on her face. “Are you alright Sir?”, she said. SIR! No one ever called me ‘Sir’! Not even waiters called me ‘Sir’. And instead of being a general source or mirth and hilarity as I expected (and as would usually have been the case in my town) I found myself surrounded by a sympathetic crowd who picked me up, brushed me down and asked me if I was OK, and sent me on my way. And I realised that no one was thinking, “who’s that clumsy oaf”, they were just thinking, “what a shame that nice gentleman has fallen down”. And at that moment I finally got it. Appearance is an incredibly powerful thing, and that realisation has opened doors that would otherwise have remained forever closed. So thank you, Sven, I salute you, and all you stand for.

  2. Michael says:

    When I sat for my first (and only) interview that launched my successful career of more than thirty-six years, the individual for whom I would work told me I needn’t “dress up” every day. That was alien to me!
    Dad and Mother were very glamorous and knew how to live–and dress. Mother often said most men looked terrific in black tie. They were stylish.
    While Mother shopped at Bergdorf, Dad enjoyed Brooks Bros. My brother and I graduated from Best & Co. and moved on to Brooks Bros.
    I learned from Dad that if you want to be taken seriously, you need not only the proper clothes, but you also need the confidence to wear them.
    I never go to a doctor’s appointment without, at the very least, wearing a blue blazer, usually a silk bow tie, and finely crafted shoes. In hospital hallways I’ve been greeted with “Hello, Doctor.” But the real reason I dress is that physicians spend more time with me than they do with patients wearing sweat pants, crumpled tee shirts, and filthy sneakers.
    And I thank Mother and Dad for teaching me how to look and feel my best at such a young age.

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