Six Outfits Every Twentysomething Should Have In Their Closet

1. The “Young Unprofessional” Outfit

A twentysomething’s idea of “work attire” can often be anything but. A button down you wore to your graduation matched with dirty black skinny jeans and boat shoes doesn’t exactly scream “401k” but whatever, we’re all figuring it out. For work attire, I would suggest investing in a blazer. They can be dressed up or dressed down. Wear them to weddings or a bar crawl; the blazer will always be your friend. Wear a nice one to work and your boss will probably be like, “This is someone who’s going places! They own a blazer so I’m sure they pay their bills on time and maybe even have a dog. Dear God, someone give that blazer a raise immediately!”

2. The “I’m Going To Score” Outfit

As twentysomethings, it’s our duty to have a hint (or more) of self-loathing about our bodies at all times. This is unfortunate, considering this will probably be the hottest we’ll ever look. We don’t have to worry yet about wrinkles or things touching the ground that should’ve stayed up. We’re in our prime with nubile flesh and perky everything! Intellectually, we’re aware of how good we have it but emotionally we’ll still say ridiculous things like, “Delete that picture ASAP because I have a Jay Leno chin!” or ‘My elbows are fat.”

Thankfully though, despite these insecurities we have, we all own an outfit that gives us confidence. Whether it’s an awesome pair of shoes, a t-shirt that makes you look muscular when you’re actually just chunky, the perfect pair of jeans, or a dress that hides your less desirable parts and amps up your assets, there’s always an item of clothing we can count on to convince others that we’re a hot supermodel and to take us home for the night. By the time our partner discovers they’ve fallen victim to false advertising, it’s too late to turn back. “GOTCHA! NOW LAY DOWN!”

3. The “Leave Me Alone, It’s So Comfortable!” Outfit

Sometimes we HAVE to go to the dark corners of our closet and pick out that one super comfortable outfit just so we can deal with life. I once owned/stole $200 sweats from a friend of mine and practically lived in them whenever I was hungover. My roommate would joke that whenever she saw me wearing them, she knew I was in a bad place. She was right. I only wear sweats when I’m feeling uncomfortable in every other aspect of my life. In that moment, they’re all I have to make me feel sane. Don’t be ashamed about wearing them! Own it!

4. The “Stand By” Outfit

When in doubt, you should always have an outfit that can bail you out of every fashion emergency (Ew, did I just type FASHION EMERGENCY?). You’re not necessarily in love with it but you know it will get the job done. This is usually a classic type of outfit—blue jeans and a white tee or an all black ensemble. These are clothes that will never go out of style. Embrace the classic look, people! It’s going to help you out immensely. Stop putting used tampons and dead birds in your hair and just wear something simple, okay?

5. The “I’m A Very ~~~~UnIqUe~~~~ Person!” Outfit

Even though I like to always veer more to the classic side of fashion, I do appreciate a kooky outfit. Gay men, for example, are big advocates of standing out in the crowd. They have a fondness for donning the following types of looks: An “IN TOO” deep V paired with “NOT DEEP ENOUGH” shorts, black capes that give the impression that they’re really FASHUN, tight jeans that require CPR for your manhood (how convenient!) and last, and totally least, an open-toed sandal moment, which can be terrifying. Exposed footwear is not a right, it’s a privilege. You don’t venture into that territory until you have a long discussion with your toe hair. Like I said before though, every twentysomething should push the envelope and have that one outfit that proclaims, “I AM ME! LOOK AT ME! WAIT, YOU AREN’T LOOKING AT ME! OVER HERE, JERK!” It’s the ensemble that’s meant to be judged and garner attention. It’s best worn at unexpected moments like the grocery store or to a house party in Bushwick, but anywhere will actually do. It’s important to take risks with your clothing, if for no other reason than to say, “Look! I sometimes wore wacky things!” when you’re older and wearing mom/dad jeans for comfort, not irony.

6. The “Walk Of Shame” Outfit

The outfit you do a walk of shame in is actually chic. You just can’t tell under the layers of vomit, tears, and shame. After all, it WAS your party outfit. It made you look good and may have cost you a pretty penny. Everyone commented on how great you looked when you walked through the door. Somewhere along the way though, it got messy. Someone spilled a drink on it, there’s an inexplicable mustard stain, and it now has the distinct smell of MISTAKE rubbed all over it. How could this have happened? It started out as THE outfit and slowly turned into EW, THAT outfit. Whatever. Walk of shame or not, you’ll wear it again. Just stop by the cleaners first. TC mark

image – © AnthonyRosenberg

Ryan O'Connell

I'm a brat.


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  • hrfe

    I think the addition of Ryan in each of these outfit types is severely needed.

  • Kai

    Get out of my closet!

    I was just explaining to someone today that I hate the way I buy clothing to do double duty as Offie Wench and Lazy Hipster. But I’ve got other stuff to spend money on (rent being top of the list) and this is why most of what I’m wearing at work today was part of my Halloween costume (part of this year’s, part of last year’s).

  • Mashka

    gotta love the multi-faceted walk of shame outfit. Awkwardly walking home in heels and a micro mini in broad daylight with eye crusties and completely bird-nestified hair.

    It’s even more fun when it’s after a Halloween party. My roommate had a walk of shame this past Halloween, texting me at noon the next day with “walking around Astoria with a catface”

    • best guest

      I walked home the morning after Halloween dressed as a stormtrooper. It was also parent’s weekend. I passed many parents. 

      • Bex

         Walked home dressed as Barbie after Halloween, the colour pink is brighter in daylight!

  • N.

    Ah, the Halloween walk of shame. A good friend’s ex is an affectionate drunk and… well, sort of an asshole. He decided to paint his entire body with green food coloring (Yes, everything. He showed me… [shudder]) and then proceeded to turn the party hosts’ apartment (including their brand new beige sofa) green and one by one, each of us along with it. I have photographs of us all at brunch the next day, green hands and faces and him sitting there, eating waffles, still completely green and grinning like… well, an asshole.

  • EP

    Well…missed opportunity for a Mean Girls quote.

    “These sweatpants are all that fit me right now.”

  • Tom

    Spot on!  I loved this!

  • klaus

    Right now I am at the age of twentysomething, so I can read Ryan’s essays. But what will I do when I turn thirtysomething? When will we begin to get articles for people who are thirtysomething?

    • hrfe

      When Ryan is a thirtysomething.

  • Anonymous

    I have a shirt that says not ashamed. I often wear it with my not-ashamed sweat pants as well

  • Madison

    “By the time our partner discovers they’ve fallen victim to false advertising, it’s too late to turn back. “GOTCHA! NOW LAY DOWN!” bahahahahahahahahahahahahahahahahah I don’t know if I’m actually laughing because it’s funny… or if it seems all too familiar…………… ………………

    • hrfe

      That could easily be in an advertisement for a push-up bra!

  • Anonymous

  • Anonymous

    not really an outfit but this article just screams “period underwear” to me *girl power*

  • Shanerowing

    Spot on! Very accurate about the lives of twentysomethings! 

  • Guest

    “look muscular when you’re actually just chunky”
    two posts in a row saying this, phrased almost exactly. what’s up, ryan?

    • Anon

      yeah seriously I’m concerned, I mean all this AND the ”
      Skinny People Need To Stop Pretending That They’re Fat” post… 

  • Guest

    “An ‘IN TOO’ deep V paired with ‘NOT DEEP ENOUGH’ shorts”
    Uh, this to stand out? Totally disagree. Nothing could be more of a uniform or look more generic. This is why I avoid the Hell’s Kitchen gay bars, among many other reasons.

  • Guest

    i wish there were photo’s… :(

  • Thought Catalog

    Reblogged this on The World Without Us.

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