1. “I’m hungover but I still want to look reasonably cute.”
There are different levels of hungover, and granted, some of them prevent you from leaving the house entirely. But if you are at the point of hungover where you can make it to the corner store to get yourself a Gatorade and maybe a meatball sub, you are gonna try to put it together as much as possible, just on the off-chance you run into someone and have to look like a human being for a minute. This outfit consists of jeggings/yoga pants, a loose-fitting sweater, enormous sunglasses, and ballet flats. Always.
2. “First date with a guy I’m honestly not that into.”
Ballet flats again, because you’re not trying to roll your ankle for some dude with a lame OkCupid profile picture. Then probably a sweet, simple dress that shows a little thigh but is still completely comfortable and likely not form-fitting. He’ll think you’re “cute and casual,” but really you’re just “lazy and planning on eating a lot.”
3. “Nailing every interview, even ones I’m not qualified for.”
This outfit is the cold, classic standby — sensible, patent heels, a pencil skirt, and a button-down. It’s the outfit you catch yourself in in a shop window while on your way to your interview and actually think, “Whoa, who is this classy, put-together bitch, because I do not recognize her???” You immediately feel overqualified for any job, even if you’re just interviewing for yet another unpaid intern ship you’ll spend getting coffee and complaining.
4. “Drinks with friends where the guy you like might be there, but you don’t want to look like you were expecting him.”
Oh, you just happened to put on the jeans that make your ass look flawless and that low-cut cream-colored top. It wasn’t like you were planning to do anything but get drinks with the friends, you just always look light and sexy. (Basically this is the outfit that really hot pilates moms wear in greek yogurt commercials — totally appealing, but effortless.)
5. “The cute outfit you’ve had pieces for, but needed a Pinterest board to bring it together.”
You always had the components, but not until you saw the post online did you fully realize how cute it could all be together. And you turn to your closet, like a wife turning over in bed and catching her husband in that perfect moonlight after 20 years together that makes him look young again, and fall back in love with every item you own. And find an errand to run that very day so you can show it off.
6. “I’m feeling heavy.”
The flowy tunic and the stretchy pants. And the Domino’s you’re going to order while looking the delivery guy directly in the eye like, “Yes, this is all for me. I own it.”
7. “Looks good from the knees down and neck up because I have no intention of taking my coat off.”
Running to the grocery store on a cold day? No need to take off your nightgown. Just layer on that chic-enough coat, throw on some boots, and make it look as though you’re wearing a functional human outfit. (Of course, this outfit immediately blows up in your face if you run into someone you know and they’re like “Hey, let’s grab a coffee!” No, you cannot grab a coffee, because you are wearing a Snuggie under your coat.)
8. “The pretend ‘around-the-house’ outfit.”
We all know what real around-the-house clothes are, and it’s probably something like “ratty old tee shirt from your high school class trip and sweatpants with a broken drawstring.” But when you message the guy you’ve been seeing like “Come over, I’m just doing laundry, we can hang out,” you cannot let him know that your hanging-out clothes make you look like a dirty Michelin man. So you put on the yoga pants, the low-cut, loose tank top, and the messy bun with the few sexy tendrils coming out of it, and pretend like this is how you dress while watching House Hunters and eating Pringles.
9. “The dress/top that looks good from across the bar/table only.”
Your boobs look incredible, but everything downward is a puffy, mushroomy, clingy-on-the-stomach mess. But the boobs look incredible!
10. “Going to see an old girlfriend that I desperately need to impress.”
This is the most important outfit of them all. It may be a solid-color dress with a chunky necklace. It may be the perfect pair of jeans with a statement bag and a crisp, white button-down. It may be a leather jacket and riding boots. Whatever it is — and it depends on the girl you’re meeting — it is your Most Realized Self, and at least two notches better than you normally look. Because there is no moment more important than “meeting up with an impeccable girl who has high sartorial standards.” It’s where you bring the big guns out.