In In my closet, Style, Wardrobe Help, Women

Style Help: Outfits that will never work because they’re unflattering unless you’re a supermodel and even then…

They may work for models or 0.1% but not for most women.

It just looks terrible or inappropriate.

5 unflattering outfits

  1. Wide legged high water pants with flats or heavy shoes
  2. Muumuus even if they look chic on others, you look like a bag lady or worse, oversized when you’re not
  3. Booty shorts or skirts unless you’re playing tennis or working out even worse are cutoff jean booty shorts that show butt cheeks
  4. Low rise pants for any bum showing your underwear
  5. Any crop top because stomach is the worst because then you get a muffin top no matter what you wear

Or you can just avoid wearing what looks trendy on most “stars” and celebrities these days and you should be all right.

Listen to yourself

Stick to your OWN style aesthetic, and what you admire on other women can ALWAYS be appropriated for your own body and style.

If you love the look of a wrap dress on someone else, try it!

If you love that they’re rocking a leather jacket with a silk shirt underneath and some jeans, then give it a shot.

It is certain that only by trying & experimentation, you will find out what you love and what you don’t.

For instance, that is how I found out that classic, tuxedo / formalwear styles really suit my personality, but I enjoy contrasting it with ripped jeans..

Or having it go completely formal but in a feminine way like below, tuxedo style!

You just have to try, but there are some things that just DO NOT LOOK GOOD.


A good rule of thumb I follow is that if something is a trend, it disappears after a year or so. If it stays on, it’s no longer a ‘trend’.

That’s why it took me so long to get onto the skinny jean boat, and the short heeled booties train.

They were classics after a year or two of constantly seeing them and now I love it.

Other trends that have disappeared without a whimper?

Harem pants. Lace booty shorts, neon colours, to name a few.

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Sherry of Save. Spend. Splurge.

Am my own Sugar Daddy. Am a millionaire at 36 after getting out of $60K of student debt in 18 months, a little over a decade earlier, using I have worked 50% of my career (taking 1-2 year breaks), and quadrupled my income within 2 years of graduating, going from $65K to $260K with an average lifetime savings rate of 50%. I have 11 side incomes that are on track in 2020 to make me $50K - $75K. I could retire today if I wanted, but love my work-life balance as a freelancing consultant in STEM (Science, Technology, Engineering, Math). I am all about balance - between time and money, and also enjoying my money. I also post daily on Instagram @saverspender.

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Posted on April 27, 2015

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  1. Tania

    “Stick to your own style aesthetic”. Yes, I agree with this however my own style aesthetic is oversized dresses (a muu muu) and I am rather short and not thin. I used to have a similar tailored style as you but as I’m getting older I care less and less about what not to wear or how to dress your body type rules. My clothing now is mainly small batch indie designers (many are sustainable). Natural fabrics that are loose are cooler in our humid weather. I love oversized pieces but with a strong architecture shape or draping worn with a bootie or espadrille wedge. Designers like Atelier Delphine, Black Crane, The Folksie Way, Rachel Craven make my heart sing much more than a skinny jean with a blazer ever did. I’ve never felt better about my wardrobe or more like me since I’ve made the switch in perspective. It is has a Japanese feel so it’s always been a popular look in Hawaii amongst older women and there have always been stores that stock these types of items from Japan. So, I think there is much more to personal style than wearing what others think is the most flattering on you. I do agree that not following trends to be trendy is also important. But the middle aged art instructor look has been around forever. I think you have a wonderful style and it suits you but I find pieces that tell me what I should and shouldn’t wear based on my body shape less interesting than I used to in my 20s and 30s. And I love when I see street style pics where one is breaking all the rules but clearly loves what they are wearing.

    1. Krystina

      Thanks for providing those designer names. The natural fabrics they use combined with the structure are amazing!

      1. Tania

        You’re welcome! Garmentory features many of these types of designers also by showcasing small boutiques from the US and Canada.

    2. Sherry of Save. Spend. Splurge.

      OOO! More clothing brands, thank you.

      Hawaii has a rich history of Japanese heritage does it not? Many Japanese folk have been there longer than “Americans” generationally-speaking, if I recall an article correctly.

  2. Krystina

    I think neon is here to stay especially in the world of fitness attire. The beauty of that is I am less likely to get run over in the gym parking lot than someone sporting all black…


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