101 Things That Happen To You When You Become A Well Dressed Woman

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Would you like to turn heads when you walk into a room? Feel unshakably confident in your body? And live your life to the absolute fullest potential every single day? If the answer is yes, then this may be the most important article you stumble upon this year.

Why is that? Because I’m about to share with you a profoundly underrated, often disregarded, and deeply criticized personal development gem that’s a complete life-changer (although you may already be in the know).

Some women may assert that it’s total BS. That it’s shallow, antiquated, even misogynous. But, I find these sentiments to be particularly disingenuous. Because the fact is that in our society, how we dress matters. And being a well-dressed woman has the potential to exponentially impact and dare I say even improve your life. Seriously. It happened to me.

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You see, I spent much of my early twenties sloppily dressing in flip flops, spandex leggings, and t-shirts every day. This was partly because I lacked confidence in the way I looked, partly because I lacked the “know-how” of putting together flattering outfits, and partly because I just naively followed all the other lazily dressed women around me.

But after living abroad for some time (France, Italy, and Latin America), seeing how women in these places carried themselves, and how their style spilled over into every aspect of their lives, my world view completely shifted. When I made dressing better a priority, it opened my life to so much improvement and opportunities I never could’ve ever imagined before.

When I started dressing better and improving my style, improving my hair and makeup seemed like a no-brainer. For my makeup to look great, I had to take better care of my skin. So I started eating better. I started working out. Before I knew it I was meditating, even reading more. I met some incredible girlfriends at my gym. I started socializing more and even met my incredible partner after years in an unfulfilling relationship.

RELATED: A fabulously curated library of  Lifestyle & Personal Development Books for women you’ll absolutely adore.

classy outfit ideas

Today, I’m on a continuous journey of self-improvement. And not just improving my style and cultivating a fabulous wardrobe. But in every aspect of my life. In no particular order, here’s a cheeky list of 101 things that happen to you when you start dressing better and become a well-dressed woman.

1. High caliber men check you out.

2. High caliber women check you out.

3. Your posture improves.

4. Your self-confidence increases.

5. You feel good about yourself.

6. Which makes you smile more.

7. Hence, people smile at you more.

8. You begin to understand the power of being a well-dressed woman.

9. People inherently trust you.

10. Hence, strangers ask you for directions.

11. Friends ask you for style advice.

12. Random people ask you for style advice.

13. People gladly open the door for you.

14. You can literally stop traffic. Cars more readily stop to let you cross the street.You understand the difference between Fashion & Style.

15. You understand the difference between Fashion & Style.


16. People become jealous and make insecure assumptions about you.

17. Most people however admire and make good assumptions about you.

18. Your friends poke fun at you.

19. Those same friends start copying your style.

20. Your social circle may upgrade.

21. You make more money.

22. You feel awkward trying new styles.

23. You see style faux pas everywhere.

24. You try hard not to judge people’s bad style, (but can’t help but pity them a little bit)

25. You get the job, (even though you weren’t the most experienced).

26. Your manager gives you a break on that missed deadline.

27. You feel awkward being overdressed, (compared to everyone else).

28. Yet you hate feeling underdressed.

29. You get over feeling awkward and embrace being a well-dressed woman.

30. People laugh at your jokes, (even when they’re not funny).


31. At hotels, you get upgraded to suites.

32. At airports, you get upgraded to first class.

33. At restaurants, you get the best seat in the house.

34. When you’re pulled over for speeding, the officer lets you go with a warning.

35. You give (and get) a small nod of approval to other well dressed women.

36. You despise clothing that doesn’t fit well.

37. You loathe clothing that is badly made.

38. Your focus shifts from quantity, to quality.

39. You cringe when you see old pictures of yourself.

40. You more often than not nail looking effortlessly chic.

41. Yet other days you still struggle to find a decent outfit.

42. People compliment you all the time.

43. So much so that you start to expect compliments; and accept them graciously.

44. Other people expect more of you.

45. You expect more from yourself.


46. People who never noticed you before, start to take notice.

47. Your vernacular changes.

48. You commit to staying fit so your clothes will look good.

49. You grow a fond appreciation for dresses.

50. Dresses become more comfortable to wear.

51. You feel naked without one staple accessory like your sunnies, watch, or handbag.

52. Your budget adjusts to prioritize building your timeless capsule wardrobe.

53. You become expert at analyzing street style, (good and bad) walking down the street.

54. People expect you to be well mannered.

55. People expect you to be smart and well spoken.

56. You can critique trends with a more discerning eye.

57. Hence, you become un-phased by fast fashion tactics.

58. Older people assume the best about you.

59. Work superiors respect you more.

60. People also feel more respected by you.

classy outfit ideas

61. You get comfortable with people admiring you.

62. You happily clear out ¾ of your wardrobe, (that hasn’t changed much since high school) to the Goodwill.

63. Bartenders serve you first.

64. They also remember your name.

65. You stop wearing flip flops (unless you’re going to the beach)

66. You’re more thoughtful about wearing gym shoes any ol’ place.

67. Ironing becomes a non-negotiable.

68. As does steaming.

69. Your boyfriend is excited to show you off when out and about.

70. You constantly receive packages in the mail.

71. You constantly have things to be returned.

72. Your dry cleaning budget doubles.

73. You learn how to hand wash clothes.

74. You know your body measurements.

75. Shopping becomes a finely tuned skill.

classy outfit ideas

76. In group settings, people want to hear what you have to say.

77. The top drawer of your dresser becomes filled with mini lint rollers, double-sided table, underarm guards, and baby pins.

78. You start reading style blogs and style books.

79. You adopt style inspiration muses.

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

81. Grooming becomes super important.

82. You experiment with different hairstyles.

83. Men value your opinion about their style.

84. Women value your opinion about their style.

85. You look forward to cold weather, because you get to layer.

86. You also look forward to spring because, florals, yes!

87. You also look forward to summer because, bikinis, sandals, shorts, hats… yes!

88. Packing becomes much easier.

89. You know a seamstress.

90. You know a shoe cobbler.


91. You ditch your high school jeans.

92. You realize just how versatile a good pair of slacks is.

93. Your wardrobe expands significantly and is versatile.

94. You swear by only felt or wooden hangers.

95. People assume you’re wealthy.

96. You always want to dress appropriately for the occasion.

97. You’re always prepared for impromptu invites.

98. You’re more engaged with life.

99. Your standards for everything increases.

100. You become happier

101. You keep pushing yourself because after all, life + style is a journey, not a destination.

RELATED: How To Be Classy — 21 Ways To Cultivate Being An Elegant & Sophisticated Woman 

Who would’ve thought dressing well could impact your life so much? To level up your look, improve your style, and start dressing better is not easy. But I promise, it’s a fun and worthwhile journey I invite you to embark upon.

Think of it like the domino effect. Dressing well can be that first (or second, or third) domino that triggers a series of positive events in your life. Dressing well is one relatively small, yet significant self-improvement step that drives momentum to live a most beautiful life.

classy outfit ideas

Interested in leveling up your look and dressing better? 

Over the last three years I’ve researched style, dressing well, and how to build a stylish wardrobe efficiently without spending a fortune on fancy new clothes. I help women do this by guiding them through building an interchangeable capsule wardrobe. 

What’s an Interchange capsule wardrobe? An interchangeable capsule wardrobe is a small well thought out collection of clothes, carefully curated to fit one’s style, lifestyle, and seamlessly interchange with each other for versatility. Want to learn how to build one of your own? Jump on over to another article I put together on how to build an interchangeable capsule wardrobe. Until next time, stay fabulous!

  • Gloria S. Martinez says:

    Awesome read!!
    Loved It!! Want to change ED EVERYTHING about… not just my wardrobe now.

    Thank You!!

    • Marissa says:

      I totally agree!! Enjoyed the read.

    • Nancy Burnett says:

      This article is sooooo TRUE I did this thru the years & NEED 2 DO IT ALLLL AGAIN 😄😄😄

    • Melissa says:

      This is so shallow

      • Diane says:

        And that’s why others got the job. Haha!

      • Ana says:

        Unfortunately, this is how the world operates. Shallow as it may sound, people do judge on the physical. Life is not a dress rehearsal and we must make the best of everyday including putting our “best face” forward to make the best first impression. Although family, friends, honesty and living a good hardworking life is most important, I too make my best physical appearance important. Feeling good about ourselves really does change life in how we treat others in a more positive way.

        • Erin says:

          Is it shallow to care about your presentation to the world? I think a lof of the criticism of this fact is born out of people that have low motivation and want the world to match their lack of effort. This goes for guys too. Someone who takes the time to put themselves together deserves a better outcome. It speaks to more than just shallow aesthetics. It speaks to effort and professionalism. Kudos to a woman who takes the time to look and feel fabulous. I often seem to think we lost a generation to feminist shaming of women being women, and rocking the distinction that we are not the same, and our differences are to be celebrated.

          • Jenaae Jackson says:

            Kudos to a woman who takes the time to look and feel fabulous. THAT PART!

      • DDE says:

        Shallow but true!

      • Debbie says:

        Shallow means ‘of little depth ‘ the author has given reasons to dress better that go way beyond shallow and she’s given much depth into why .
        Dressing better shows respect for oneself and therefore the world around you respects you .

      • Abby says:

        In life as at the beach, you must go through shallow to get to deep.

    • Gzd says:

      Just perfect! Thank you for writing this great list!❤️

  • Kremena says:

    Recognize myself in many of the items. After reading your list, I no longer feel awkward, as I thought I was. Thank you!

  • Archana.Nath says:

    loved it.want to change my look now.

  • Catherine says:

    True on all points!

  • Nzinga says:

    Great list! I’ve been striving to stay consistent with dressing well daily for a while now. It really does lift my spirits and keep me in the mindset of a high quality woman. ❤️

  • Kelly says:

    Excellent! Read the entire article in excitement. It was very honest and much appreciated.

    • Loretta says:

      You just feel good about yourself. I find it a way of living and loving one self.
      A little effort goes a long way

  • H. Newsome says:

    Thank you and please keep me informed about info, changes and styles that are beneficial for a classy woman.

  • Kimo says:

    On point…..

  • Victoria says:

    I think I’m the past I have given up on dressing classy but I want to give it a shot. Even if I’m just going to the grocery store. It will make a huge difference

  • Angela says:

    I love being well dressed wherever I go. This lists gives me some added thoughts to consider .

  • I have a friend that wants to make a change in her life. You mentioned that by dressing well, people tempt to make good assumptions about you. I will let her know what I’ve learned, so she can consider the idea of spending more on her clothing.

  • Rachel Lynnie says:

    i liked them all.

    especiall point no.67 haha

  • Mary kimani says:

    I love the good information. Very helpful. These are definitely experiences that will happen as a result.
    About others who feel its shallow or full of grammatical errors, read it again and realise this is a simple english read, with basic requirements met. It speaks to everyone.

  • NuMe Nicole says:

    absolutely on point it is just how it is when you dress well it gets others attention and it is powerful especially when coupled with great character

  • Mrs K says:

    “Well-dressed” is relative. Everyone looks good in their own eyes. Waiting for other people to compliment you shows that one has low self esteem.

    Different jobs and different lifestyles call for differing fashion sense.

    Look your best according to what suits your occupation best. Be comfortable in your body and you will not wait for others to boost your self esteem.

    No pressure 😍😍

    • Jenaae Jackson says:

      💯! Well dressed to me is looking and feeling your absolute BEST. Indeed this is different for everyone.

  • RIA says:

    #57 UNFAZED 😉

  • Susan says:

    Hmmm! I’m definately into dressing better lately. And yes, I cringe thinking that I hated being in photos way back because of what I was wearing…!
    I enjoy experimenting and feeling good and comfortable in my skin.

  • Marc says:

    what’s the name of the writer who wrote this

  • Margo says:

    Why is trying to look your best shallow? I don’t agree. My mother always wore makeup and had her hair done. I grew up watching my mother get ready every day. She was a stay at home mom.
    My mother worked hard to make sure people looked at her hair, her face, and her clothes so they would not concentrate on her feet. Born with two club feet in 1920, she suffered all her life but always had a smile on her face. There is nothing shallow about that!

  • Annerose Kmoch says:

    I suggest the Mini Venice bag from British brand DeMellier London in the shade forest or cognac $495.00 or better the large size for every day.

  • […] order to be a well-dressed woman, it’s important that your clothes fit to perfection. If you’ve got a knack for sewing […]

  • Ej says:

    How can I follow you on Instagram?

    • Jenaae Jackson says:

      Hi Ej,

      Follow us on Instagram @quarantineglowupgang after May 1 it will switch back to @hellobombshellx

  • Michele says:

    if you’re sporting an HERMES bag no one will assume you’re wealthy. you ARE wealthy.

  • Taya says:

    Was so happy to see in this list some of the things that I already have in my life even though I’ve just started my well-dressed woman transformation =)
    enjoyed the article so much! it’s so inspiring to keep going!
    Ironing was on of the things I hated the most I used to buy clothes that doesn’t wrinkle (we all know that is not natural fabric) but now I have no chioce haha considering buying a steamer and find a seamstress
    A couple of days ago a stranger asked me for directions XD

    The thing I really struggle with is to be dressed up even if I need to shop a dozen of eggs in the store nearby such a headache no to look overdresses for that… Do you know some quick ways to dress elegant yet casual?

  • Kristen James says:

    You speak my language fluently “dawling”!!! Adored this!!

  • Tanya says:

    Loved this! Thank you.

  • Panda says:

    This is a total eye-opener for me!
    I am a Japanese blogger and am planning to post about dressing better in my blog. I would like to incorporate some aspects of this post into my blog.
    If you are looking into expanding your field into Japan, I would like to help by translate your posts to Japanese!

  • Debbie says:

    Shallow means of little depth , 101 reasons go way beyond shallow so therefore it’s not shallow .
    It shows you respect yourself in more ways than one and when you respect yourself so does the world around you . The author is correct and it’s true .

  • Barbara says:

    I love this! Dressing has become much too casual. Taking care of yourself is so very important. I hope that women take your advice!

  • Lisa McCullough says:

    Great article, all true, I would say I am 70% of the way there, I always loved looking elegant but didn’t find my confidence till now at 47, body positivity and a wider range of sizes have made it so much easier. I am freed from any attempt to impress anyone but me, and I love it! Lisa

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