My Back to School Outfit From 1998

Before you see this picture, just know that my outfit for the first day of high school was actually awesome. I wore a floral skirt with a sheer black overlay (which later became known as the “cursed skirt” because I always tripped and fell or spilled something all over myself whenever I wore it).

Pictured below is what I wore when I entered 10th grade.

I remember specifically choosing this dress because I felt as if it really complimented my figure. And obviously comfort played a strong factor, why else would I choose to pair it with 100 pound white old-lady sneakers?

So maybe I didn’t get proportions right, or maybe later on in high school I got the Jennifer Aniston hair-cut that ended up looking like untamed helmet hair. Regardless, I had the right thought process down.

Here are the three things to keep in mind when dressing for a big day…

first day of school ootd

1. Pick something that makes you feel like the best version of you.

I wore this lavender dress because I knew I had some pretty awesome curves to show off, and that made me feel good about myself whenever I wore it.  That allowed me to walk through the halls confidently that day.

2. Make comfort a priority.

Whether it’s the first day of school, or the first day of a new job, there’s a plenty of uncertainty to go around. The last thing you want to do is be uncomfortable. Be sure to wear something you won’t have to tug on or readjust, and always go with a pair of shoes you can walk confidently in – as long as those shoes don’t look like the chunkers I’m wearing ;)

3. Don’t do anything to your hair that’s going to have you second guessing yourself all day

I.E.: do I need more hairspray? Are my curls still there? Go with your easiest style, saving the more complicated ones for after you’ve settled in.

You have a lot to offer this world, set yourself up to present you most confidently!


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