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How to Dress for Things You Hate
How to dress for your terrible office job:
Black pencil skirt, large-print silk blouse, great bangles, tight smile that masks your inner hatred, heels that make your ass look great while people metaphorically try to kiss it.
How to dress for a dreaded double-date:
A dress loose enough that you can sigh easily, comfortable shoes for frequent walks to the bathroom, pockets for easy phone access, necklace for fidgeting.
How to dress for a restaurant job that you got out of desperation after getting fired from your office job you hated:
Black tights with runs in them, empire-waist black dress with cap sleeves and a low neckline, restaurant clogs that you hope will transition well enough to after-work social functions, earrings that maintain your sense of dignity.
How to dress to go fight with your boyfriend:
Baggy old sweats, comfortable boots in case his roommates are home and you have to take a walk, no makeup (in case of crying fits), sexy underwear.
How to dress to go break up:
Just call, it’s 2014. Then crawl into bed naked and watch TV until you fall asleep.
How to dress for your first day back to the gym in four months:
Whichever gym shorts still fit and don’t chafe, your cutest sports bra. Socks with no holes (even if they don’t match). T-shirt with the cut-off sleeves from that weird event to promote the latest Ryan Gosling movie that your best friend dragged you to.
How to dress for a first date that seems promising but might be awful because you just broke up with someone:
Flouncy red dress from the $29.99 sale rack, gold accessories with personality (a weird brooch!), those old-fashioned tights with the line down the back of the leg to keep with the retro theme, comfortable black ballerina flats so you don’t trip.
How to dress when you think you’re going to get back together with your ex-boyfriend:
Those jeans he always said he loved your ass in, tight tank top to emphasize how cut your abs are from the 9 time you’ve worked out since he last saw you, light cardigan to keep it casual, boat shoes (he likes those too).
How to dress for a job interview for a job you might actually love and excel at, which terrifies you:
Least-holey black tights, colorblock dress with empire waist (only been to the gym 9 times still), black leather jacket that you bought as a Christmas present to yourself, white knit hat from your childhood that you stole back at Christmas (for comfort during the commute: remove before interview).
How to dress when you’re going to a party with your ex-coworkers and the boss that fired you:
Your freakum dress. Ariana Grande curls. A business card holder that holds stacks on stacks for that new, kickass job. Champagne flute as a mandatory accessory at all times.
How to dress for a six-hour bicoastal flight home for Christmas:
Stretchy leggings of any color, loose tank top, a hoodie with deep front pockets to hold your iPhone so you can still listen to music even while carrying 3+ bags. Flats that you can remove while you try to sleep in your seat on the plane, enough makeup that your mom won’t worry about your health (but no eyeliner, which will smudge all over your face immediately upon contact with the airport).
How to dress for a serious family conversation:
The sheep + cloud pajama pants you and your mom made together one summer, big, big comfy sweatshirt that makes it feel like someone is hugging you, thick wool socks preferably home-knit, no makeup (you will cry), no phone and an open mind.
How to dress for a long walk through the snow with your family before they’re three time zones away again:
Long black and red vintage Woolrich coat that you could’ve only found in an Oregon thrift store, the necklace your mom put in your stocking you’re pretending not to hate, a scarf your sister made you, a single, contraband American Spirit to sneak-smoke later.
How to dress for the first time you have a New Years Eve with your ex-boyfriend who’s your boyfriend again:
You don’t hate this. Go to the party full of people you love. Wear whatever you want.
Caitlin Cristin White is a writer who lives in New York City. She likes puppies and poetry but hates phonies. She lives in praise of the mysteries.