In #OOTD Daily Style, Style

Sherry’s #OOTD Outfit of the Day Style & Fashion Look: “The Inspired By Pretty Woman 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 Inspired By Pretty Woman Look

This reminds me of that polo match scene, except her dress was a latte brown (a terrible colour for me), and the polkadots were oversized (also not my thing). I like a smaller polkadot because it looks like a neutral print, and the way that this print is all over the place, gives me something new to look at.

I normally would not go with spaghetti straps on a dress because my shoulders are larger than the rest of my body (no, really.. they are, I am an inverted triangle shape), but I loved this dress SO MUCH, I broke my own style rule and got a dress that accentuates my shoulders.

I added the red belt because I cannot resist a good navy + white + red story, and this belt is silk, handmade, and stolen with permission from my mother’s closet because she was a real clotheshorse. Plus, the red belt really highlights my waist and gives me some sort of definition.

I also have this (and other) beautiful gold lace cuffs that I can mix and match any time I want. I picked this particular gold cuff that is no longer sold, but this Pegasus one would have done the job just as well. If you want the lace cuff that is ridiculously out of my price range but something I totally covet, you can check out this one which I AM IN LOVE WITH.

My whole thing as I have gotten older, is to wear comfortable shoes. Enter: WEDGES. You get height, you get a sleek look, and your feet are comfortable. They no longer sell this particular style, but I would in a heartbeat, buy these wedges from Cole Haan in its place as they look almost exactly the same.

Oh. And the sunhat. That’s what covers my Pretty Woman look, where I feel like I am at this virtual movie polo match because of it. A HUGE BIG ASS SUN HAT. It’s fabulous. And dramatic. I especially love the pop of red on the dress the more I look at it. The dress did come with a polkadot belt in fabric, but as I always do, I tend to chuck these belts aside and wear another belt completely out of its zone to personalize the dress to what I think it should look like on me.

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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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  1. June

    What I love about all of these looks is how you complete the style with neutral shoes. I have this awful compulsion ( I think from growing up in the 60’s, to play matchy, matcha with shoe choices. Black shoes with black dresses and blue shoes with blue dresses and pink shoes with ,,,, well you get the picture.

    1. Sherry of Save. Spend. Splurge.

      It’s a common compulsion.. I think people in the past were all taught to match their handbags to their shoes and their clothing, but that’s no longer the case because it looks too matchy-matchy! Unless you’re the Queen, this is an old style rule. It’s hard to break however πŸ™‚

  2. Belle FrugalFord

    I think because the neck sits quite high for a v and it’s not super fitted in the top you look perfectly proportioned despite it not being your first choice of strap 😘 wish you would style me. I’m an hourglass πŸ€·πŸΌβ€β™€οΈ

    1. Sherry of Save. Spend. Splurge.

      I would love to style you lol.. I need to see your closet, your things on… but yes, this is a size medium not a small dress so it’s a blousier version rather than being very fitted, which I ended up loving.


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