I Don’t Know What to Wear!


Very rarely do the words, “I don’t know what to wear,” come out of my mouth. Usually, when I have some sort of event scheduled, my outfit is the first thing I plan. Sometimes I even have outfits for occasions that aren’t ever going to happen—do you know what I mean? For example, I have a look I could wear to a high tea party in England, but obviously, that outfit will never be worn. My point it, it’s very strange that I had no idea what to wear last Saturday night. I wanted to share with y’all my struggle and what I ultimately wore to this special “event”…


We were traveling out of town for a mini vacation, and while there, we planned to have dinner with the family of the boy I like! So not only was I going to see this boy, I was going to see him in front of both my and his parents…talk about awkward.

The first issue involved traveling. Like any normal person (wink wink), I waited to pack until ten o’clock the night before we left. So of course it was very unfortunate to find that a lot of my clothes weren’t clean…Strike 1. I only had room in my suitcase to pack one pair of shoes, which had to be these rain boots due to the inclement weather of our destination…Strike 2.

So already right there, I had a lot of obstacles and limitations. Since my parents were going to be at the dinner, I knew I couldn’t look like I was trying too hard…which eliminated any clothing options that were too tight or showed too much skin. Well then, I knew it was going to be cold, so I had to wear some sort of layer or jacket on top.

Finally, it was supposed to be a casual dinner, so I couldn’t look too dressed up, but I also didn’t want to look too casual or sloppy. I never thought I’d feel this way about clothes, but I was stressed out about what to wear! By this point, I had basically narrowed it down to about six tops and two pairs of pants. Which of course, needed to match these brown leopard rain boots. I wanted to wear the top from this post because I think the color looks good on me, butttttttt it was dirty. Figures. But really, it’s my own damn fault, so my lesson to you is this: don’t procrastinate. 😉

With all of these restrictions, I finally decided on this outfit: the brown leopard rain boots (obviously), my favorite black pants, this blush chiffon blouse layered under a jean jacket, a brown belt to tie in the color of the shoes, and some sparkly accessories to add a bit of girliness to the look. I felt pretty good after coming up with this outfit, and I thought it turned out cute for Saturday night. In hindsight though, I should have worn the red top…This blush color really washes me out, especially in these photos. I knew that going in, but I thought if I added a sparkly necklace and jacket on top, it wouldn’t be so bad. I guess I was wrong.


[Goofy photo alert] So even though this isn’t the outfit I would’ve picked out if all my clothes were clean and there weren’t so many limitations, I did find this look pretty cute, especially with the flower pin. But I’d love to know: do you ever feel stressed out about what to wear? What sort of event or situation makes it difficult for you to plan an outfit?

Have a super fantastic weekend!


Miles of smiles,



Blush Chiffon Blouse: Nordstrom Rack, $20 // Jean Jacket: JCPenney, $19 // Black Skinny Pants: A.N.A. via JCPenney, $25 // Leopard Rain Booties: Ralph Lauren via JCPenney, $60 // Aviator Sunglasses: Icing, $16 // Blush Statement Necklace: DSW // Brown Belt 

3 thoughts on “I Don’t Know What to Wear!

  1. Maryjaneorourke February 23, 2018 / 8:37 AM

    Whose the guy


  2. Carrie at Curly Crafty Mom February 25, 2018 / 11:04 AM

    That floral pin is so cute on the denim jacket. I just love lighthouses, such a great place for a photo shoot. And, those leopard boots are adorable!



    • Graceful Rags February 27, 2018 / 10:18 AM

      Thanks so much Carrie! Yah, lighthouses are always so pretty 🙂


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