Valentine's Day 2020: A Dork's Style Guide To Date Night


I am a vain dork.


Which means on the inside, I wholly identify as this:





But outwardly, I aspire to look like a slightly doughier version of this:




It’s a conflicted life: to want to be grafted in as the fifth Kardashian while fully acknowledging my head size and agreeable head-nodding nature would make me the perfect human Muppet. Ah... the toils of finding a social tribe.


And if this inner turmoil were not enough, this oxy-moron of an identity gets more complicated when you factor in the trials of navigating date night as a vain dork. The goals of a vain dork in any romantic eating escapade are as follows:


1. Shovel copious amounts of breaded, fried morsels into my mouth WHILE

2. Looking like a second-string runway model AND

3. Feeling lazy-Sunday-morning comfortable


While the family of 5 nestled deep in the recesses of my belly would argue that I am an all-star when it comes to feeding them exorbitant amounts of buttery fried regret in every eating endeavor, romantic or otherwise, I have never been able to successfully achieve the aforementioned goals 2 and 3 in the same sitting. Excess food, beauty and comfort in one setting are the stuff dreams are made of and some would argue cannot possibly coexist in one sensible date night.


I would wholeheartedly agree… if it were not for the events that took place on February 14th, 2018.


One Foxy, Flatulent Night

This is one such date night that will live in infamy. It all began when my beloved partner in crime orchestrated a night of romantic wonders, filled with sonnets, roses and spritely animals who sporadically broke out into surprising renditions of 80’s hair band ballads… well, more like he made a reservation at a restaurant that had dim lighting and required shoes for patronage (snobs). And when shoes are demanded of you and dim lighting befalls you, the only proper response is to dress up.


For this special evening, I chose an off-shoulder velvet dress that made me look like Audrey Hepburn’s long-lost Asian sister. Even better, its empire waist meant that I could partake in some unadulterated eating while still maintaining adequate levels of style ferocity.


Had I cracked my own vain dork goals?


Barring an arm sleeve that was beginning to cut off circulation, a tyrant of a neckline that threatened to expose a pair of innocent boobs with one wrong turn, and a dress that had no additional give… yes, I do believe I cracked the code entirely.


What is more romantic than an evening of exchanging longing gazes with your entrée? What is sweeter than the sound of your lover’s voice calling to the waiter for a fourth and fifth round of bread baskets?


The evening was an absolute dream.


Except somewhere between free bread basket 3 and 4, my tight arm sleeves began to take a turn for the worse and cut off blood supply to my hands. But I consoled myself and remembered that tingling and temporary loss of motor function is the price you pay for style ferocity and bread sticks. Life would go on. But what I was not prepared for and would not wish upon any mortal woman began to take place. The lack of elasticity in my dress forced me into an evening of belly clenching and sucking in so tightly that my lower extremities began to give way. And just as the waiter arrived with the check, I involuntarily released a very slow audible feminine fart into the shared atmosphere with top notes of cedar and truffled meatball and base notes of utter terror.


I suppose this is the price you pay for trying to have it all.


But I have learned much since my evening of romantic flatulence. And while I certainly did not crack the code then, I think I may have found the holy grail of date night outfits that are equal parts comfort, ease and gluttonous adventure.


Draping and The Little Details


When it comes to date night, there is power in simplicity. No one wants to feel uncomfortable with a reduced eating capacity because of a poorly chosen ensemble. For this first look, take your favorite pair of dark washed jeans and pair it with your favorite neutral tank or tee shirt.


“But wait, I’m going to a Michelin starred restaurant - how dare you! You lying harlot!” you might be wondering to yourself.


Don’t fret. From here, I always love to pair the casual ensemble with a draping outer layer. Sometimes called a waterfall cut, other times referred to as a cascading hem, this flowing outer layer - be it in the form of a thin cardigan or a thin jacket - adds femininity and incorporates the best parts of a dress (the flowy parts of course) right into a casual outer layer.


Choose a cascading outer layer length that hits at or just below the hips and be sure to utilize the superpowers of tucking in your top to showcase a model-esque leg line. Cuff your jeans and pair it with a fierce pair of neutral ankle strapped heels. It’s a very small detail, but choosing a pair of ankle strapped heels elicits sentiments of “Special” - it’s like a fancy necklace for your ankles. Even better, the ankle straps offer a bit of assurance that you won’t step barefoot onto the street after a night of drinking.


To tie it all together, a neutral clutch will signal to the world that an evening of romance awaits you. While you likely carry some form of oversized purse every day, the small clutch and its impractical storing power signals a marked distinction from the day to day and lets the world around you know that there will be an enchanting love-filled evening to be had.


Jump In To Romance


From the cradle to the grave, the jumpsuit is a rare style staple that will flatter you through the ages. It’s an inter-generational all-star, looking just as mesmerizing on a toddler as it does on Grandma Gertrude and every life stage in between. The genius of the jumpsuit is that it can offer the glamour and glitz of the best dress in your closet while giving you the mobility to twirl and prance without the fear of showing onlookers your lady bits. Ah, the wonders of pants.


The key in pulling off any jumpsuit that is date night appropriate boils down to color and pattern. When choosing your jumpsuit, opt for deeper richer hues like burgundy, navy or deep emerald greens. The deeper the color, the more evening appropriate. Pastels and patterned prints, while adorable in their own right, should be reserved for summertime farmer’s markets.


Styles that are fitted at the waist and looser along the leg line tend to be universally flattering. If you are a taller gal, a wide legged jumpsuit that hits just below the ankles will be your best option. And for shorter ladies like myself (5’4” and below), a jumpsuit that is slim on the legs and hits right along the ankles will lengthen your frame and be your winning ticket to comfort, beauty and perhaps an additional bread basket. The only request a jumpsuit makes of you on date night is to reunite it with its two long lost loves, the ankle strapped heel and neutral clutch. Commit to its request, and you will be the fiercest woman in any room.


Two Foxy B’s: Bomber and Bodycon


It's likely you have a fancy (but not ball-gown-fancy) dress in your closet that you have worn once but have no idea how to wear again. You adore it, but it’s too fancy of a dress to wear to date night, or any night, really. But every once in a while you see it in your closet, drape it over your head, squeeze it tightly and hum Whitney Houston’s “I Will Always Love You," only to put it back knowing fully that you will never be together again.


Tragic. But I assure you, I have found a way for the both of you.


I understand the heartache that comes with owning a gorgeous dress that cannot be appropriately worn. While a jean jacket can neutralize and bring balance to many dresses, it simply won’t work for date night. Pairing a semi-formal dress with a jean jacket in this instance runs the risk of you looking like you were caught in an emergency and put on the first two things you could find in your closet. I know you’ve thought about it. Don’t do it. Instead, pair your dress with a bomber jacket.


The bomber is a modern-day flight jacket that hits right at the hips and brings effortless cool and structure to any outfit. It provides an elevated outer layer that can tow the line between semi-casual and semi-formal. Put it on and it instantly changes the tone of your dress, giving it an air of casual edge while still creating a cohesive outfit for date night. The bodycon cut dress works best with the bomber as it is a straight cut that sits closely along the silhouette. The bomber is typically less fitted and offers more of a boyfriend cut, which provides balance and contrast to your oh-so-fancy dress.


Put these two together and you won’t know whether to declare yourself gorgeous or a bad ass - but why limit yourself?


A Dork’s Date Night Blessing


May this tale of date night, flatulence and the litany of dreams any modern woman would hope to achieve in one evening inspire you to what is possible in a date night ensemble. Abide by these guidelines and never again will you need to decide between elegance and a gluten-filled orgy with a breadbasket. Heed this vain dork’s advice and the world will be yours. Well, at least for the evening.


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