In #OOTD Daily Style, Style

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

Street Style to me, is the epitome of this. Short boots, mixed with leather jackets, and a kind of office-style look underneath. I mean, the tame version of the look, not the kind that I cannot wear comfortably.

The draping on this skirt is beyond magnificent. If you have a chance to buy this Lenox skirt, run don’t walk to buy it. It’s amazing.

I picked the grey in the boots to match the grey in the jacket, but also because the tassels of the boots match the tassels of the jacket as well. It’s like a match made in heaven, these two pieces were meant to go together.

I find grey leather jackets way easier to wear with my outfits than black. It looks less harsh to my eye, and still adds a gravity to the look, yet a soft one, like a raincloud rather than a tornado or something. Grey leather jackets would be my #1 purchase suggestion if you are in the market for a leather jacket (your first one).

The navy blue in the Breton stripe top (CLASSIC!) matches with the navy blue in the skirt. The stripes of the top, also matches with the pleating in the skirt at the waist, around the curves, and it’s why the two go together so perfectly.

The necklace is a geometric, bold yet stylish statement piece by Québec artist Claudine Moncion who works a lot with copper (exact necklace here). It’s perfection. Like a frilly copper curve circle, crimped and beautifully feminine yet simple.


These boots are perfection by Rag and Bone (my favourite bootie makers), and I bought them half a size larger so I’d be comfortable, and could wear socks in them without them being too tight. They’re great. I especially love these because the heel is also covered in the grey suede and isn’t a wooden block of any sort, which makes it all look completely suede and tailored.

I also love the dip in front of the booties, as it elongates the leg and doesn’t cut my leg off as I want every inch of height I can get.

Super comfortable, sexy, slouchy, and somehow it all goes together. The look is perfect. Even for an office look in an environment that’s a tiny bit more casual, like business casual.

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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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