What to Wear If You're on the Fence About Going Out

Some nights can two ways: Either I'll be out with friends or I'll be on my couch watching an infomercial for knives at 2:00 a.m. Here's a hot look for both scenarios.
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Kelsey Lawrence
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Some nights can two ways: Either I'll be out with friends or I'll be on my couch watching an infomercial for knives at 2:00 a.m. Here's a hot look for both scenarios.

We know how to dress for most of life’s basic events: weddings, funerals, job interviews. If we don’t, there are plenty of resources that will tell us how. But what about other less obvious occasions, like that job interview for an ambiguously casual start-up or a coffee date with a professional contact? Or maybe you’re meeting up with an attractive coworker. Do you dress for a date or a weird hangout? 

As someone who likes to moderately stand out, I value the importance of dressing for the occasion. This little series will feature looks for those bizarre occurrences in life where you just don’t know what to wear. First up, I’ve assembled some options for a Friday night where you have every intention of going out, but probably will end up on the couch at home.

The night always starts out with good intentions. Things could get wild! You’ve texted a few people, you’ve remembered that your old coworker is throwing a housewarming party that could get a little weird but you’re kind of feeling yourself tonight. You put Ciara’s “1,2 Step” on. Who knows where this night could go?

Actually, we both know. You can feel it in your bones already. Several tacos were consumed and you’re feeling kind of gross. Oh, is that a marathon of "Forensic Files" till 1:00 a.m.? But whatever. You’re still YOUNG and FUN. Maybe you’ll wait for a text from your friend and see how it goes, you know.

OUTFIT 1: Black crop top + leggings + blazer + gold hoop earrings.

Here’s the secret to a versatile Friday night look: athleisure. Both form-fitting and stretchy, comfy and sweat absorbent, sportswear transitions beautifully from your couch to the dance floor, then quickly back to your couch again. Say what you will about the short-lived phrase of “health goth,” but Alexander Wang was onto something!

black crop top and leggings

Can you tell I normally don’t do fashion blogger-style photos? My backdrop is more high school prom.

Going out in anything that’s not very, very comfortable has always been vastly unappealing to me. This is why I worship leggings. They adhere to my ass, and they allow me to pre-game with a basket of tortilla chips and at least two tacos and STILL be hot to trot. For this look, I suggest searching for vintage athletic wear on Ebay (i.e. Adidas crop tops), or visiting any mall store both cheap and geared toward a high school demographic.

OUTFIT 2: Sweatshirt + black skirt + necklace + boots.

Look number two exemplifies a good rule of balance: Take one thing from your grandma’s closet and one thing from your teen sister’s closet. This is a good maxim for fashion in general. The skirt says let’s party (maybe!!) and the sweatshirt says, “Hmm, is that a headache coming on? Let’s go lay down!”

What to wear outfit.

I plan on wearing fake, gold jewelry with colorful athletic clothes until I'm an old, gray lady.

A sweatshirt layered over a crop top accommodates a multitude of scenarios. Out for drinks with your coworkers? Sweatshirt on. Went over to your best friend’s house to watch Lifetime instead? Sweatshirt on. Receive an upsetting text and said, “Fuck it, I’m going to Booty Night at [insert local dance club]”? CROP TOP TIME.

Khaki Lighting Print long-sleeved sweatshirt, $26; Adidas Originals Double Logo T, $29; Talula Manhattan legging Aritzia, $22; Similar Girl Props Bamboo hoops earrings in gold, $5; Kelsi Dagger women's Jupiter boot, $63; Polyvore.

Khaki Lighting Print long-sleeved sweatshirt, $26; Adidas Originals Double Logo T, $29; Talula Manhattan legging Aritzia, $22; Similar Girl Props Bamboo hoops earrings in gold, $5; Kelsi Dagger women's Jupiter boot, $63Polyvore.

Only one more night until Friday! Now we have outfit options for the hypothetical parties we could be attending as we speed toward the theater to watch Fifty Shades of Grey and yell things at the screen. Although I’m a big proponent of things too tight, too short, and too brassy, comfort is the rule supreme. Colorful sweatshirts and stretchy materials transition beautifully between someone’s patio/drinks/early 2000s hip hop and couch/burrito/"Real Housewives." 

Next up: What to wear when you need to pretend to be rich.