How to make ANY outfit look good.

September 12, 2017 in Lifestyle - 9 Comments

How to make ANY outfit look good.

September 12, 2017 in Lifestyle - 9 Comments


There were two things that I wanted to be as a high school freshman: a Varsity cheerleader, and the lead in the school play. As a quiet, mousy, afraid-to-even-raise-her-hand-in-class kind of kid, these seemed like totally normal things to want. I was too shy to ask a question during English class, but getting up in front of everyone during a basketball game and jumping around in a short skirt? That sounds GREAT! Sign me up. There was a guy I liked on the basketball team.

I mean, of course there were OTHER reasons I wanted to be a cheerleader – because it’s a SPORT. And a healthy extracurricular. And a great opportunity to build life-long friendships with my other cheer… mates? Cheermates? Is that a word? Cheer friends?

Whatever. It was mostly about the guy. And everyone knows cheerleaders are hot.

So I dragged my friend to try-outs with me – you know, because I was too afraid to go alone – and together we learned all of the basic chants, stunts, cheers, I think there was a dance involved? The only thing I can remember is thinking how they made everything look so much easier in “Bring It On”. I couldn’t even do a cartwheel, let alone the front handspring-stepout, roundoff back handspring-stepout I had planned to blow everyone away. You know, if I practiced enough. How hard could it be? It’s just, jumping around. On your hands.

I did the splits for my “stunt” portion during try-outs. That was one of the things – you had to do a “stunt”: a cartwheel, a roundoff, a handspring, you could even do a forward roll if you weren’t coordinated enough to do anything else. Which I wasn’t. But I chose to do the splits, because I decided that a forward roll might be too dangerous for someone inexperienced like myself.

Also I thought the splits would be more impressive. Which they would have been – had I actually done them, instead of whatever I did. Because what I did was slide down about halfway to the ground, until my knees started to bend and my legs made this triangle shape with the floor, and I was like “Ta-da!”

Hah. Hah. Hah. Oh, right, did I mention I’ve never been able to do the splits?

I was shocked (I know!) when I didn’t make the team. The squad? I don’t know, whatever. My dreams of becoming a Varsity cheerleader that year were squandered, and the only thing I had left – the ONLY other thing I wanted – was becoming the lead in the school play. Because, for some reason, I thought this would make me cool. “She’s the LEAD in the school play”, they’d say. “She’s going to be a star!” Like lead in the high school play is the first step to Broadway.

There was also a boy. In the drama club. And I liked him too, and wanted to impress him with my amazing acting skills, because I thought that I had amazing acting skills. Kind of like how I thought I could do the splits for my cheer try-out. I had amazing, and slightly unjustified, confidence as a fourteen year old.

Of course there were OTHER reasons I wanted to be in the school play. Because it builds a healthy level of charisma and increases skill in public speaking, and… it looks good on college applications? Probably? I don’t know. Whatever, we both know it was mainly about the guy.

So I tried out for the school play, and had much better luck than I did with cheerleading, because this try-out didn’t require me to dance or jump or do anything that required any sort of coordination. All I had to do was say some lines and, I don’t remember – fake cry? Pretend to be scared? I forget what the play was about. I wasn’t in the play. MY part came during intermission, when the drama teacher decided that there should be a MINI PLAY. While everyone in the REAL play is backstage changing costumes and re-setting scenery, there can be another play going on to distract the audience. Like a commercial. But it’s a play. A five minute long play. While everyone in the audience is getting up to go to the bathroom.

BUT – the real meat of the story here, folks –  at least I was IN the play. Kind of. And not just as the girl who pulls the curtain. And so was the guy that I liked! He was in the crappy intermission play, with me!  Turns out he couldn’t act either. So at least we were in this together. Maybe we would have a super romantic kissing scene and he would have some sort of line that confesses his love to me and he would realize that he has REAL feelings for me as he’s saying the line! And then we’d live happily ever after! It would be just like “A Walk To Remember”…. without the singing, and the cancer.

Oh, the big dreams that I had.

So we got our scripts, and our lines, and our parts, and I was like “THIS IS IT. THIS IS THE BEGINNING OF OUR LOVE STORY.” because we were being cast along side each other – so OBVIOUSLY it had to be a love story. What kind of crappy play was this supposed to be if the only two characters don’t fall in love?

A crappy five minute intermission play, that was kind of crappy play it was supposed to be. I don’t actually remember the storyline of this play – that’s how bad, and weird, it was. I was the “star” and I don’t remember the storyline. But I remember the guy that I liked played a chicken.

Yea. Like, a chicken. A “cluck-cluck”, down on the farm, lays eggs, has feathers (his part didn’t have any lines) CHICKEN.

And I was not a chicken. I was not the hen that he falls in love with and lives happily ever after and lays a bunch of eggs with (because that would be a weird play). I was a farmer.

Yea. Like, a farmer. To be honest, I don’t remember if I even had lines. I don’t remember what this weird, little play was supposed to be about. All I remember is that I was supposed to dress up like a farmer, alongside my co-star, The Chicken, and we walked around on stage in a circle. I think maybe he was supposed to be, like, a “prize chicken”? Maybe the story was that I was trying to sell him? Or sell eggs? Or BUY eggs? I don’t remember. The whole thing was very strange. No wonder why this was only a five minute long play.

The guy that I liked – the Chicken – was not super on board for this. Because he was a fifteen year old boy being asked to cluck around like a chicken on stage in front of, you know, people. His friends. His family. The basketball team. And I was like, “Ugh. I knoooow, right? This is so lame!” – meanwhile, in my head, thinking – “How can I make this farmer outfit look sexy enough that it will make him fall in love with me?” 

Co-stars fall in love all the time. Just look at Brad Pitt and Angelina Jolie. Before they got divorced. It can happen.

So I went home and tore through my closet. I couldn’t just be a farmer. I had to be a FASHION-Y farmer. A HOT farmer. Not “hot” like, working out in the field all day kind of hot, but “hot”  like – “Damn. I never knew she was so hot.” kind of hot. You know? Like if Britney Spears dressed up as a farmer in one of her music videos, what would she wear?

Of course, I probably wouldn’t be allowed to wear that. This was a high school play, after all. And I was, like, fourteen. So I told my parents what I’d need to buy for my take on a “farmer look”.

“Heels. Brown ones, you know, since I’m supposed to be a farmer.” (I don’t know what brown heels have to do with farming, but it made sense at the time.) “And a black turtleneck, and tight overalls. And a hat.”

And my parents said, “No.”

“Aren’t you supposed to be a farmer?” My mom asked. “You need like, a plaid shirt.” 

“But the black turtleneck will look better with the overalls.” I said. “And I need to look for a hat.” 

“Like a straw hat?” 

“No, ew.” I said. “A floppy hat.” 

You know those floppy hats girls are wearing now that it’s Fall? That’s the kind of hat I was talking about. With my overalls, and my heels, and my black turtleneck. Because I wanted to be a sexy, fashion-y sort of farmer. Not, like, a real farmer. I wanted to impress my co-star by letting him know that I could make ANY OUTFIT look cute. Because THAT’S what fifteen year old boys are impressed by… a girl who can really glam up an outfit.

My mom didn’t let me wear any of that. She said I didn’t “look the part”. (I don’t see why not. I’m sure plenty of farmers wear high heels.) So I went out there with a plaid shirt and regular shoes and overalls and braids in my hair. And I was like, “If only I could have dressed how I WANTED, this story could have had a totally different ending.” And my mom was like, “Just say your lines” and my co-star was like, “I hate this. Why am I chicken?” 

I ran into a similar situation in college when I was working as a server at a winery, and the uniform attire was supposed to be “All black – black pants, black shirt, black non-slip shoes” and I was like – No prob, Bob. I got this. Because, obviously, in order to perform my job well, I need to feel confident by looking good. And it’s hard to look good when you’re wearing non-slip shoes. So I spent over $100 on Sketcher brand non-slip shoes designed to look like regular black flats, that ended up with spaghetti sauce stain and smelled like sewer water by the end of it. But, you know, at least I looked cute.

The key to feeling confident in any outfit is make sure it flatters your body type. When I tried to go for the “sexy farmer” look, I wanted tight overalls. Enough to suck in my stomach. That’s pretty much the key I go for in any clothing situation – if I want to look good, I try to find something that sucks in my stomach. Because I don’t do crunches or any sort of ab workout beyond the occasional yoga move. So, I rely on clothes to trick people into thinking I look good naturally.

Accessories also play a huge part. When I was server, I used to wear small diamond studded earrings and a necklace to dress up my uniform. Headbands were also a big thing, since we always had to have our hair pulled back.

The most important part though, is to make sure that YOU feel good about your appearance before you even put on the clothes. When your hair is done, your nails are done, and your make-up is on point, it’s hard to lack confidence no matter what your outfit looks like. If two people are wearing the same thing, but one of them didn’t bother to fix their hair or put make-up on, they will look sloppy and less confident than the person who did. So make sure that you’re taking care of yourself! Self-care is so important when it comes to confidence.

What are some of your tips for making any outfit look good? Share in the comment section below!




  • Chelsea Moore September 13, 2017 at 12:32 am

    I totally agree with you that self-care is so important to confidence! The days I don;t do my hair or make-up and never feel as good pr productive as days I spend getting ready to look put together.

    • Jenn September 13, 2017 at 5:19 pm

      Same here!! I always feel better about myself when I’m put together! 🙂

  • TheSunshineTiara September 13, 2017 at 11:52 am

    Very well thought and well written blog! Loved every bit of it!!

    • Jenn September 13, 2017 at 5:16 pm

      Thank you!! 🙂

  • lynifrika September 13, 2017 at 4:18 pm

    This is so funny! I’m sure my mum would have said the same thing to me, NO! I’m pretty laid back now but before I would use scarves to enhance my look, or glasses, or jewellery. It depended on what I was feeling.

    • Jenn September 13, 2017 at 5:16 pm

      I love scarves in the fall!! And I’m a big fan of sunglasses. I always try to wear them in pictures and my boyfriend will tell me to take them off because they’re on in EVERY picture haha

  • CLAIRE UNVEILS September 14, 2017 at 11:04 am

    belle sleeves!!! sooo gorg!!


  • […] year all about “Fall fashion trends that you probably already have in your closet” and “How to many ANY outfit look good” (that one actually wasn’t so popular – but I’m linking, it because >I< liked […]

  • Leave a Reply

    Oh, Hello!

    Let's stay in touch! Leave your email address below and I'll let you know every time there's a new post.

    Join 1,473 other subscribers