The Only 5 Fashion Tips You'll Ever Need To Know

For the last 25 years, I’ve been wearing clothes with varying degrees of success. I eventually got it together though and realized that you have to kiss a lot of high-waisted skinny jeans and ill-fitting t-shirts before you find your fashion Prince Charming. Here are some tips I wish I knew before I left the house looking like a bloated hooker in high school and college.

1. Unless you’re an Olsen twin or a starving teenager in Ethiopia, avoid wearing oversized clothing

During my sophomore year of college, I decided that it would be a really chic idea to start wearing size X-large t-shirts and pair them with my black skinny jeans. I was convinced that the size inequity (tight on bottom, loose on top… wait isn’t that the title of a gay porno?) would make me look skinnier and thus more desirable to all the fine gay specimens at my state school located in Daly City. So I did it. I spent the next four months wearing giant t-shirts that looked like maternity clothing and honestly thought I looked flawless. My delusions were crushed, however, when I went shopping with a gay friend of mine, who actually was super, super Teen Vogue intern skinny, and saw him try on a size X-large t-shirt. On his waifish body, it actually resembled a nightgown whereas on me it just looked puffy and strange. Seeing him swim around in the shirt like a tiny gay jellyfish, I realized that’s what it was supposed to look like. Lesson learned. Unless you’re skeletal, wearing oversized clothing doesn’t make you look skinnier, it just makes you look like like you blacked out and bought the wrong size at the store.

2. Don’t cave to pressure from sales people

I used to be the worst at this. Someone could try to me sell a $500 latex body suit and if they were hot, I’d be like “kay.” I used to go into this really hip and expensive store because I had a crush on one of the workers and I swear to god, I spent a few hundred bucks on the weirdest stuff just because he would smile at me. I would just black out when he shot me one of those looks and tell him “Yes, I would like to buy the Rodarte lace tuxedo. Why not? I need it, right?” Jesus, that crush was expensive. I’ve learned the error of my ways though. Now whenever someone tries to sell me something I know I look terrible in, I just think “COMMISSION, COMMISSION, COMMISSION,” and it works like a charm.

3. Don’t buy things that are too small

This seems like a no-brainer but I think it’s something we all struggle with. At this point, we know something fits the second it hits our body. It’s not some science. It’s not going to grow on you. You’re not going to suddenly love the way it makes your chest look lumpy. I used to buy clothes that would serve as motivation to get in better shape but, shocker, that never happened. As a result, I have a closet full of clothes that could only fit my ten-year-old little brother. We know when something fits good and we will wear the crap out of it until it falls apart. I wore my favorite pair of jeans even when there was a giant hole in the crotch because I couldn’t let go. I still keep them today even though I wore them to literal sheds because I’ve deluded myself into thinking that I’ll one day become a designer on Project Runway and repair them myself. The point of this is to say that finding something that will fit you like a glove is rare but that doesn’t mean we should settle for anything less. If you don’t feel comfortable in something the first time you put it on, you’ll never wear it.

4. Don’t follow the trends if the trends aren’t following you

There are so many people who wore high-waisted shorts and skinny jeans out of some misguided sense of duty to the fashion trends and they just shouldn’t have. Their body wasn’t made to wear high-waisted shorts (Spoiler: very few bodies are). If a fashion trend is made popular by Kate Moss, chances are it can only be worn by toddlers and other fashion models. That woman has the body of a 12-year-old girl, for god sakes. What looks good on her frame will not look good on 99% of the population. Back in the day/gay, I used to wear the tightest skinny jeans imaginable and it made my legs look like sausages. Now I know very well I don’t have fat legs but when they’re squeezed into a style meant to accommodate Pete Doherty, they’re going to look a little inflated, so I had to stop wearing them. Do yourself and your body a favor by just wearing things that will make YOU look good, not some anorexic 14-year-old Swedish model with no tits.

5. When in doubt, just wear black

New York taught me this rule and I’ll forever be indebted to the city because of it. Ever struggling over what to wear? Just wear black. I’m serious. If you’re a girl, just put on a black dress and call it a damn day. If you’re a dude, just wear black boots, black jeans, a white t-shirt (to avoid being too goth) and a black jacket. Done. Wearing black makes everyone look a little bit more high fashion, which is ridiculous because it usually requires no innovation or skill. When I dress head to toe in black, it doesn’t mean I have a good fashion sense. It just means that I was too lazy to put in any thought to my outfit. It’s your go-to, your “Get out of fashion jail free” card. Use it! TC mark

image – Deon Moritz

Ryan O'Connell

I'm a brat.


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  • Alyssa

    THIS IS DUMB.  Just because you are large does not mean you can insult people who are not.

    • Sarah L. Keziah

      It was pointing out the obvious, someone who is average or overweight won’t fit into the same styles a skinny minny does.  

      Plus, who cares. If you wanna make a skinny joke make em.. you wanna make a fat joke.  Make em.  Every size hears them, people just need to stop being so damned sensitive. 

    • padface

       What? He’s not large, he just said he’s not super thin…

    • NICOLE

      He was just saying that you should wear clothes that flatter your body. Everyone is different and not everyone is going to look good in the same thing. 

    • Jordana Bevan


    • Guest

      Where did he insult not large people? Sensitive much? Also, on the Kinsey Scale this article rates a gay as fuck (not that that’s a bad thing).

    • Jesus

      Gurl, calm down. I don’t think he was being offensive. It was just some light-hearted comedy meant to do no real harm. 

  • BAT

    #5 = GOLDEN.

  • Opik

    I found this mildly hilarious. Always love Ryan’s sense of humour. In respect with this profane dictum, number five tip is really helpful, and I’m gonna adhere it to my brain.

  • padface

    I do number 3 all the time. Sigh.

    I usually reserve black for when I want to look like a bamf, but generally I don’t do black. I guess because I’m quite pale and don’t want to look like a big emo. But yes sometimes when I just don’t care I throw on my black boots and black leather jacket, because you just cannot go wrong.

  • Anonymous

    #5 needs to be written on the face of the moon.

  • cat

    I wish everyone in the world would read this and take some well heeded advice. Also, you should discuss with American Apparel what ads they decide to put on your page. They’re trying to sell oversized sweaters and thigh highs….as an outfit.

  • Sama

    Basically, just buy something that is in your size, preferably in black, that is unpretentious, and you will be FINE. 

  • LaTourista

    But it’s the sexiest 12 year-old body i’ve seen.

    • None

      Pedobear, is that you? Yes or no, that’s a creepy comment.

  • Kmodek

    My personal fashion advice: just because its made in your size does NOT mean it looks good on you. (Skinny jeans, I’m looking at YOU!)
    When I weighed 270 pounds, NOTHING looked ‘good’ on me. I definitely didn’t go for anything tight, but when you’re that big, there IS no style that looks good. You pretty much just get by with whatever you can actually get into.
    Now I weigh 135, I’m 5’9″ & I’m like a kid in a candy store when buying clothes because everything fits and looks alright.
    Unfortunately, now I’m paranoid that my butt is flat, I have no boobs, & saggy skin.
    I’ve come to the realization that no matter what size you are, you’ll always feel imperfect because you’ll only look like a 23 year old when you’re 23, not when you’re 40.
    It ould be nice if society could acknowledge and accept this so we can all feel good about our bodies instead of always feeling imperfect, because we ARE all imperfect!

    • ENDI

      Speak for yourself.

  • Kmodek

    And yes, everything I own is black, white or gray. Makes it really easy to match outfits without a lot of work!

  • Elnora Hawley

    I love that the ad on the sidebar for this article is a chick wearing high waisted tight ass skinny jeans showing us her bum…and even though she is a stick thin American Apparel model – she still looks kinda fat.  Unflattering, people!

  • Sophia

    Man, all I ever wanted was the waifish skeletal look. And so I’ve been there on #1, saying “hey, let’s go for the Natalie Portman in Black Swan, skeletal-dancer-in-oversized-clothing” look. And on someone like me, who’s pretty curvy, I’m pretty sure it fails. But I’m in self-denial, so I keep trying it.

  • Thekogs

    “starving teenager in Ethiopia”
    Does no one see something really wrong with this line?

    • Lora

       NOT cool to simultaneously make light of something as serious as starvation, while making a small-minded, blanket assumption about what it means to be “ethiopian.” wildly offensive and alienating to your readership that hails from the country (me!). hadn’t realized that i didn’t fit the racial profile of your intended audience, sorry about that! BYE 

      • Safy-Hallan Farah

         I co-sign as a TC contributor and East African.

  • Wawa

    it’s funny how right below the article, an american apparel ad flashes some anorexic 14-year-old swedish model with no tits wearing high waisted shorts and clothes that’ll fit 12 year olds.

  • Lauren

    (tight on bottom, loose on top… wait isn’t that the title of a gay porno?)  HAHA

  • NoSexCity

    Sticking to good old number 5 forever. #fashiongoth

  • inihos

    Reblogged this on Vanity Kit and commented:
    What else does one really need to know about choosing the right clothes… almost nothing i reckon.

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