In Month of Style, Style

Best & Worst #OOTD Outfits from 2020

Here are what I consider to be the hits from 2020. I didn’t really start posting “daily” outfits until June, so this isn’t the entire year, but there are a lot of outfits I am surprised by that I would absolutely wear again and enjoy wearing.

I am also doing this as a way to see what my uniform / style is like. I think I can hazard a guess with a few words:

  • Not sloppy
  • Contrasts (oversized + oversized doesn’t work for me)
  • Less bohemian, more corporate/preppy
  • Long skirts need heels or else I feel frumpy
  • Layers need belts
  • Long dusters and cosy sweaters
  • Monochromatics/Neutrals (White and White, White and Blue)
  • Nothing super body conscious

You can click on all of the summary links above each set of posts to see the notes/details in the earlier months. From September onwards, each individual photo has its own separate OOTD page.


Favourite Outfits from JUNE 2020


Favourite Outfits from JULY 2020

Favourite Outfits from AUGUST 2020


Favourite Outfits from SEPTEMBER 2020


Favourite Outfits from OCTOBER 2020


Favourite Outfits from NOVEMBER 2020


Favourite Outfits from DECEMBER 2020



Things I really liked this year:

  • Magenta Pink + Red together
  • Drapey asymmetrical dresses and tops
  • Loose oversized sweaters with skinny jeans
  • A new venture into athleisure as a style (sweatpant skirts for instance)
  • Layering items, like an army green jacket over a cashmere sweater, or the army green jacket with black ribbed leather sleeves peeking out
  • Long dusters – either vests or sweaters
  • Split back tops
  • Tie-cuff sweaters
  • Ripped jeans with gold sneakers
  • Using button-up dresses as dusters / open sweater coats
  • Monochromatic looks – black on black, all whites, all greys…
  • Oversized button-up shirts with skinny jeans
  • Widelegged pants and trousers


Outfits from JUNE 2020

Outfits from JULY 2020

Outfits from AUGUST 2020

Outfits from SEPTEMBER 2020


Outfits from OCTOBER 2020


Outfits from NOVEMBER 2020

Outfits from DECEMBER 2020


Things I did not like this year:

  • Trouser pant looks – I feel like I am moving away from bootcut pants
  • Anything too tight and uncomfortable/fussy
  • Anything that was oversized + oversized – this bag lady look thing is not my jam
  • Anything too casual – sneakers with dresses and a casual sweater? No.
  • Putting oversized items on sleek outfits – it works in some cases but not in all
  • Dull / drab basic b*tch outfits where there’s nothing interesting
  • Anything out of proportion – too long skirts without heels; hemming will be key
  • Fussy looks – I knotted a top but found it turned it into a crop top which made me uncomfortable

If you want to see more looks:

I summarize the monthly looks in this Month of Style category with links to each individual look that can be seen as I post as my outfits of the day every other day as a second daily post with prices and way more photos under this Style category #OOTD Daily Style category.

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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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