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giggles, style hacks, and inspiration for your personal style story

Crushing Style With My Style Crush Issa


We have a problem.


Issa Rae and I share the same first love.


Some refer to this 2X3 foot wonder formally as “mirror,” but Issa and I affectionately call her by her colloquial name: “Mirror Bitch.” She is our confidant, our sounding board, our emotional solace.


And naturally, anyone who has ever had a “Mirror Bitch” knows any intrapersonal turmoil can be resolved standing before her in hushed and modulated whispers with the stink of morning poo still in the air without a single witness.


It’s where we have both simulated aggressive pick-up lines…


Reassured ourselves that we are in fact still queen of our domain…



For Issa and myself, a mirror (and any reflective surface) is an ally, a makeshift therapist - the original hype woman.


Issa Rae and her wonderfully awkward antics and grumblings on HBO’s Insecure grafted me into super fandom from day one. As obsessed as I am with her mirror rants and tirades, it’s actually her show-stopping style distracts me from even her best lines.


Issa is the intersect of 2 things I may hold most dear: copiously stylish and copiously funny. Her outfits are as sharp and edgy as her biting wit, and her mix of color and pattern just makes you want to giggle and smile.


Come, let us admire her together!


Not Your Grandma’s Floral Blazer


When I think of floral blazers, 2 people often come to mind: my mother at the height of her real estate career and Blanche Devereaux, the sultry geriatric southern bell of the Golden Girls. And while both are fierce in their own right, my style endeavors will never be to emulate that of a 90’s era realtor or a flirty southern grandmother. While its overly padded shoulders and tight intricate floral patterning could run the risk of you being mistaken for a cousin to the accent chair in the past, floral blazers have made a comeback.


The key to win with a floral blazer is to ensure that it exists as the stand alone piece as Issa has done here. Every other separate needs to play second fiddle to this boisterous signature item. The more color you layer with your floral blazer, the closer you tread towards Blanche and her grandma posse.


Here, Issa keeps the look modern with a boyfriend cut blazer which is looser fitting and by choosing a larger floral pattern in some peaceful neutrals. This pattern creates visual interest without wreaking havoc on the eyes. To bring continuity to the outfit, she used the blazers color palette of mustard yellow, blues and browns and subtly weaved it throughout her outfit. If you have been tempted to try out floral blazers but have been anxious of looking too much like a geriatric flirt, follow Issa’s ways and reach for a neutral patterned palette with a boyfriend cut. This blazer has the power to punctuate even the sleepiest tee shirt and jean ensemble you throw its way.


The Star of Stripes


When it comes to stripes, we are often told to be careful as too wide of a stripe can widen your frame and too colorful of a stripe can lend itself to giving you some circus clown vibrations. But here with champagne in hand, Issa demands you to throw caution to the wind and join her in some re-imagined striped possibilities. The beauty of her outer layer is that its intense vibrant stripes are housed in a structured and classic military jacket. With its cuffed sleeves, shoulder buckles and multi-pocket detailing, it blends funk with toughness while being the perfect canvas for a more vibrant family of stripes to play on. If you are ever worried about being “too much” when it comes to your striped endeavors, the rule is simple: the more vibrant in color and dizzying the stripe, the more structured and tailored its back drop should be.


And with such a busy outer layer, you might guess the inner layer should tone it done a notch… only to hear Issa classily commanding us, “Bitch, bring on the stripes.” Similar to the floral blazer above, her striped jumper ensemble pulls from the same color family of the military jacket, creating a blended sense of continuity for the outfit and allowing her to play with varying stripe breadths in the second layer without it ever seeming a little extra.


While you may look at two items in your closet and bat them away as “too much” when paired together, you will never know the kind of magic that can be had until you try it on in real time. I wouldn’t have put those two items together initially, but now you might catch me sipping a bit of champagne one day marvelously striped head to toe.


The Mash Up Queen


I am a mash up enthusiast, but Issa is a seamless mash up queen. By mashing up elements from two different genres of style (such as casual and formal wear or feminine and masculine silhouettes), you can create something new and visually surprising to the sleepy eye. Issa effortlessly does this here with a fitted and stripe cuffed polo with a form fitting a-lined skirt, stirring all kinds of curiosity and stylistic intrigue.


Mash ups create unexpected looks and signal to the world around you that you are an independent thinker because quite frankly, there are more ways to wear a pencil skirt than with that sterile old camisole. If you find yourself a little groggy at the style wheel, I implore you to “shop your closet” and consider mashing up two genres that you otherwise would not pair together. My favorites involve pairing a form-fitted formal-ish dress with a chunky casual sweater that hits at the waist, or an office appropriate pencil skirt with my partner’s ironic oversized graphic tee’s pulled and knotted at the waist. If you are looking for a bit of visual sizzle in your wardrobe but don’t want to break the bank, follow Issa’s example into your closet and mash away.


Holy Crop!


Cropped jacket, crop top, cropped pants and somehow tastefully covered for daytime? For those of you who consider the crop top a pernicious trend attacking the likes of tweens and daring grandmothers alike, perhaps this ensemble may change your mind. While I have certainly seen crop tops woven into flirty outfits, I have never seen an entire ensemble dedicated to the crop. Here, Issa sports a crop top with a pair of high rise cropped blue trousers and a cropped jean jacket.


The high rise trouser disguises the crop top while simultaneously showcasing a tiny waistline as it hits at the narrowest part of her waist. The high rise pants work to showcase an elongated and exaggerated leg line as they create the illusion of a leg line that starts just after the waist. And while you can’t see it here, the crop of the pant hits right at mid shin, showing a bit of appropriate daytime skin. This ensemble is all about playing with proportions, keeping it different while varying one similar croppy theme. To ensure that all of the magic of a tiny waist and an elongated leg line that the crop has created is not hidden, she finishes the outfit with a cropped denim jacket that hits right at the waist, bringing continuity and uniformity to this playful yet modest ensemble.


It Is-sa Success!


Whether it be how to avoid looking like a circus vagabond through the appropriate use of stripes or how to transform grandma’s blazer into something visually masterful, Issa has taught me to keep the rules of style open and flexible. As long as your outfit creates intrigue and flatters what you have intended, your look works. If you find yourself in a spat with your current threads and looking for an adventurous upgrade, I am certain your Mirror Bitch will be all smiles and affirmations when you adopt Issa’s rule-bending, self-affirming sensibilities.


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