15 Struggles All Style-Challenged People Face

My whole life, I’ve struggled with finding my own “style,” and finding whatever the “in style” of a given year is. I always find myself one step behind, like when I finally discovered leggings under skirts, that was already uncool. Sweater dresses? I was about two years late to that game.

Now, thanks to Pinterest, I’ve gotten better at my style game – well, at least with finding what’s in style. I buy these super stylish items, only to look absolutely ridiculous when I put them on. Like for real, how do you people make baggy sweatshirts and leggings look cute? I’m genuinely curious, because I just look homeless when I do it.

Hair and make-up is a whole other issue. I didn’t discover the miracle that is liquid eyeliner until I was 23. I still don’t understand contouring. I look like a panda when I try to do “smoky eyes.” I never even bought a hair straightener until I was in college. I cannot be the only person who suffers in fashion purgatory.

1. Layering. Seriously, how does one wear a flannel shirt under a cardigan under a vest without looking like the Michelin man? I see people do it, but I’m convinced that they’re not actually layering. No, these people have sewn collars and cuffs onto their sweaters.

layering

2. High Heels. You can’t tell me that those things are comfortable. I see women running around – literally running – in these things like it’s no big deal. Meanwhile, I keep my Converses in my car so I can take off my heels before I even get home.

high heels

3. Smoky Eye Makeup. I’ve tried to do this so many times, and every time it just looks worse. Am I just too cheap to buy good makeup? Is it my lack of hand-eye coordination? WHAT IS IT?

smokey eye

4. Pixie Cuts. Only some people are qualified to rock this haircut, and I am not one of them. I haven’t tried, but I’ve had short hair and it looks nothing less than heinous. I envy the stylish pixie cut people who don’t have to, like, do their hair for the majority of their morning routine.

5. Mix-n-Match. I never quite understood this concept. Here’s how I used to go shopping: “Oh, the outfit on the mannequin looks cute; I’ll buy that and only wear those items together.” I would buy two or three cute, prepared outfits at a time, and that was it. I wouldn’t wear things with each other because OMG WHAT IF THEY DON’T MATCH?!

mix match fail

6. Short and Tights. Again, this always looks cute on other people. I just look like I’m seasonally confused. Teach me your ways!

7. Chunky Sweaters. Once again, I look like I am homeless when I wear these. They don’t hang right on me, I can never seem to buy the right size (do I buy them bigger or in my size?). I wear them anyway because they’re comfy, but I never look cute doing it.

chunky sweater

8. Colored Skinny Jeans. Are my legs just not long and lean enough for this? Or are they just poorly designed? I can only pull off dark colors, like maroon or brown. Bright colors just seem to enlarge my already abnormal leg muscles.

skinny jeans men fail-KNkd

9. Glasses. I’ve worn glasses for almost ten years, and I never look adorable and sophisticated. No matter what kind of glasses I try, I just look, well, dorky.

glasses

10. Curling Irons. How on earth do you people have the skill and patience to battle one of these beasts every morning? I have tried countless times, and every time I look like I stuck my finger in an electrical outlet. Is there a secret? A trick? WHAT?!

curly hair

11. Sneakers. I sincerely wish that it was socially acceptable to wear Nike running sneakers everywhere. Sadly, this is not the case. Unless of course you look cute doing it with your PINK attire. I just look like a soccer mom. Whatever.

12. “Statement Jewelry.” Oh, just wear this super flashy necklace with your plain black sweater and you will look fabulous! Uh, no.

is this a weapon or a necklace?
Is this a weapon or a necklace?

13. Midi-Skirts. It’s like all of a sudden the modest look is cool, but only if you have the legs of a six-foot-tall model. These things make me look stumpy, not cute. I can’t make these look good. I can’t.

14. Rompers. I adore the idea of wearing a dress without actually wearing a dress. I think rompers are one of the greatest fashion inventions of this decade. If I could only wear them without looking like a 5’5” three year old, that’d be great.

15. Hats. How does one wear a hat and not look like a trucker? I just want to know.

hats

Samantha Glassford

A born-and-raised Jersey girl with a chronic case of wanderlust, Samantha spends her days reading, writing, and planning adventures. She currently teaches classes at the community college while living at home with her parents, trying and failing to become a part of the proverbial real world. Her dream is for someone to pay her for writing and traveling, but in reality she'll probably be teaching forever. Follow her mundane musings on Twitter @SamanthaG2012, and check out her personal blog, wanderlustingmillenial.blog.com

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