You know those days when life has worn you down, and you have to attend a social function in the evening and you are SO not feeling it? You feel lumpen/bloated/zitty/tired/ill, and everything in your closet seems to mock you. Every garment seems hell-bent on making you look like the least-cute version of yourself that you could possibly be. That dress is stupid and too young for you. Those sandals pinch your toes. The waistband of those pants only feels good about twice a year, right after a case of the flu. Long story short, you’d like to curl up on the couch with a bag of Cool Ranch Doritos and watch something asinine. But no! You must venture into the cruel world, where you’re sure everyone will look better than you and be having way more fun.
Chin up, little bunny. When life hands you lemons, tell those lemons to fuck off. My fashion advice for when you’re just not feeling it is simply this: Go tough.
“Going tough” means giving up on pretty, and working with the bitchiest, rockinest look you can get away with. You’ll feel more comfortable for starters, and you’ll hopefully project an attitude that suggests you’re so cool, you just couldn’t be bothered to dress up—while still looking foxy as hell. And that’s infinitely preferable to having pinched toes and a sour expression all evening. Who knows, you might even end up enjoying yourself!
Wearing “Casual Tough”:
If the occasion is just drinks, a launch, or a gig, go with jeans that you love and feel good in, although the darker and slimmer the better. Add a rock t-shirt, a masculine-cut tank top, or an untucked button-down in any colour, as long as it’s black or white. Converse All-Stars, lace-up boots, or any heavy soled footwear complete the look. Bare feet are totally tough, but flip-flops never are. Try not to carry a purse if you can manage it. We’re going for off-duty rock star here.
Icons of casual tough: Patti Smith, Chrissie Hynde
Wearing “Dressy Tough”:
When you’ve got to look a bit more pulled-together, the goal is still to look like you don’t really give a shit. “Underdressed” is usually something I avoid, but here, it’s the whole point. Keep the jeans if you can get away with it. Black cigarette pants can also work, but don’t wear them with a top that makes you look like you’re part of the catering staff. A leather or jean jacket is wonderful here, as is a black turtleneck or a Hanes white t-shirt. Skip the jewellery, save for a big silver cuff, a man’s watch, or a chunky ring or two. Hold the gold! If you can stand it, wear wedges or boots with a heel—the highest and meanest-looking you can manage. Nobody ever looked like they could kick ass in a pair of ballet flats.
Dressy tough icons: Kate Moss, Joan Jett
Makeup: You’re looking to strike a balance here between looking like you don’t care and not actually caring. Do something simple but bold, and pick one thing to focus on--lips or eyes. My decision-making process goes like this: If I’m going to be eating or drinking a lot (no comment), I go with the eyes. Take a black eyeliner pencil and line around the entire eye. It’s okay if you half-ass it, because you should immediately smudge the heck out of it with a finger or a q-tip or something. You want to look like maybe you haven’t taken it off since yesterday (you animal, you). Lips are easy—go red or don’t bother. This requires that you own, enjoy, and feel confident applying and wearing red lipstick. If you don’t, we can work on that later.
You’re done. Shove a couple twenties in your pockets, flip your head upside down, mess up your roots, and get the hell out of there. Everyone will think you’re super cool and you can get away with either sulking in the corner or being a loud, obnoxious drunk. Ladies’ choice, bitches!