In #OOTD Daily Style, Style

Sherry’s #OOTD Outfit of the Day Style & Fashion Look: “The Olsen Inspo Look”

I post my outfits on the blog every day at noon (12 p.m. EST) under this Style category #OOTD Daily Style and then I do a summary of all the looks in my Month of Style roundup at the end of the month.

The Olsen Inspo Look

I don’t know why, but I felt like pairing an oversized sweater under an oversized jacket. I am also making an awkward AF pose in this shot because I was trying to show the back of the sweater being longer than the front, AS WELL as showing off these gorgeous, balloon-style sleeves on this beautiful wool bomber jacket that was done by Olivia Palermo in a collaboration.

I paid a discounted sale price for the bomber, but almost returned it (glad I didn’t!) because I wasn’t sure how much wear I’d get out of a bomber jacket. I am not a casual-style kind of woman, and athleisure is a wading style pool I am slowly dipping my hesitant fashion toes into, so I ultimately kept it because it was like a stylish, formal version of something that is quite casual (bomber or varsity jacket).

Some people didn’t love how wide or clunky the sleeves were, being pleated and so on.. but I kind of like the look.

I had just wanted to wear the bomber (that’s how this look started). I wanted the bomber jacket, and thought – a tight top underneath? Nah, that’s what I always do. Very predictable. How about something.. oversized? And the bomber over it, in like an Olsen-twin, homeless kind of inspo.

From there, it was just a matter of what bottoms – jeans? No, too casual for the look I am going for, and I aptly added leather leggings not from their brand The Row, but Helmut Lang in a suede, not a leather (which yes, I could have also done and did consider).

I also decided it was too much athleisure for me, so I added the high heels.


The leggings are actually suede in a dark navy-ish almost black colour by Helmut Lang. The back is comfortable and jersey, the front is suede, and it has a nice matte, leather look.

I decided to pair it with some olive green heels from BR (they’re my favourite brand for reasonably priced heels) rather than my usual brown leather suspects from Manolo Blahnik, and a really bright pop of colour (I can’t help myself) in a statement ring my YSL from their Arty collection which is now discontinued.

It’s from their limited edition run for Valentine’s Day, which is why it is red, and says the word “Love” on the back.

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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 TheBudgetingTool.com. 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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