A couple weeks ago I went to the bar downtown and I met a really cute guy. He bought me a drink, we talked, and had a great time. Unfortunately, he was not from around here. I thought it would be a one-time thing and it would be over. We would never see each other again. To my surprise, last week he texted me, asking me to get drinks with him because he would be in town for business meetings. Of course, I died of excitement.

We were supposed to meet on Wednesday, so all week long all I thought about was what am I going to wear. I wanted to make a really good second impression since I the first time we met it was a bar. I went through my close probably about ten times without exaggeration. I asked multiple friends for advice, but I still couldn’t figure out what to wear.

First, I thought about wearing a super casual outfit, but I decided against it. Then I was sure I should wear a Burgundy T-Shirt dress with black booties. I thought the T-Shirt dress would make it casual, but the booties would make up for the casualness. I convinced myself against that because I didn’t want him to think I had put too much thought into it. As you can see I over thought my outfit A LOT.

I ended up wearing some dark wash skinny jeans from American Eagle. For a top I wore a burgundy tank top. I wore black booties and a navy blue watch. I straightened my hair and tried to make it casual, but also a little grown upish.

I over thought my outfit way too much, and ended up wearing something super casual. The important thing to remember is that you have to be comfortable with your outfit. I think I looked pretty good, he thought I looked pretty good- so it all worked out. The key is not to overthink it. Be yourself and wear your favorite clothing- odds are the guy probably won’t care that much about your outfit.