In #OOTD Daily Style, Style

Sherry’s #OOTD Outfit of the Day Style & Fashion Look: “The Casually Disheveled 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 Casually Disheveled Look

I don’t love this look 100% and I was trying to figure out why. Is it the pants? Is it the proportion? Is it the boots? Then I realized, the more I look at it, that the outfit was fine, but it felt unfinished to me. I needed a coat with it. Or a topper of some sort like a leather jacket to finish the look because bare arms + boots = sort of odd.

I should have added my grey suede leather jacket to this, and it would have tied in the grey suede to the boots, and finished the look to be a true Autumnal season look.

I also think the trousers are not quite right for the top because they’re too formal + work-y, and this top is anything but (have you seen how deep this neckline goes? I need to wear a bralette underneath or else I am going to flash everyone in a bra). I should have worn this look with black waxed jeans, or leather leggings, it would have gone better with the vibe.

I chose the belt because I liked the idea of a tripled ‘wrapped’ belt (it’s just one belt that looks like it’s multiple belts), going with the drape of the top having multiple layers. I also definitely needed to belt this top (in my head) because without a belt for my waistline, it is really loose and drapey, like I took a grey blanket and haphazardly covered myself in it.


On the one side, I have a vintage Hermès men’s watch done in 18K plated gold, with roman numerals for numbers (that’s what sold me on the watch in the first place) and it’s an older men’s watch because the dial is so big. Women’s watches in the past were tiny and just for ornament, not for real use, but MEN.. had real watch faces that you could read easily, as they were a B-U-S-Y gender unlike women.. /sarcasm.

I added the watch strap to this to be double wrapped because it was sold without the original strap, or any strap at all worth wearing (it was sold with a crappy piece of leather with STAPLES IN IT), and I like the dark brown double wrapped look, which goes with the double/triple wrapped belt look in the outfit. The leather straps go together in my mind.

For the edgy part of the look, if the top wasn’t enough, I wore my HUGE bismuth Adina Mills ring. I definitely overpaid for it on Poshmark (the seller accepted a little too quickly), and I love the kind of dinosaur-ish vibes I get from it, and how it glints so beautifully in the light.

Please note the CUFFED trousers, and the fact that these boots are tasseled which is a fun detail, but even more fun to walk in when you feel your feet swish (brings me back to when I was 5 years old with my favourite tasseled shoes). The other great detail about these boots is that the HEEL is also covered in suede. Normally these boots have a stacked wooden heel, but this one happened to be completely done in dark charcoal suede which made me pay more for them than I would have.

I especially like boots that loo like this with a curve in the front to show your foot because it elongates your leg, and doesn’t make it look like one blob of fabric + boot. The look of a completely covered boot can also be cool, but difficult for petite women to wear (I am 5’5″ and on the cusp of being petite) as it cuts off the look and length of your leg when it’s completely encased in leather.

When you show a bit of skin (I should have maybe cuffed these trousers higher to my ankle), it looks much slimmer and cooler as an edgier look because it shows your ankle, the thinnest part of your leg, and has some definition to the look.

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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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