Thrifted Anniversary Dress // A Night At The Vineyard

When it comes to planning date nights, my boyfriend and I are the absolute worst. Between my indecisiveness and his short attention span, it takes forever to decide on something to do. But there are three things that get me every single time — dressing up, wine, and my favorite man. So, when Chad suggested that we spend our anniversary at the winery, I was very excited. What can I say? I guess the man knows his the way to my heart after eight years.

There is one thing that I am decisive at though — choosing my outfit. A few months back, I thrifted a long-sleeve, boho-looking dress that I fell in love with as soon as I saw it hanging on the rack at Goodwill. Actually, I didn’t even try it on. I just picked up the Earth-toned, bell sleeved dress and knew I had to have it.

The pretty little dress sat in my closet for months. It was too dressy for everyday wear, so I was waiting for the perfect occasion. An eight year vineyard celebration seemed like the perfect time. But enough with me explaining it, just see for yourself!

I am seriously obsessed with this dress. Thankfully, despite not trying it on in-store, it fit me perfectly and made me feel so great. It wasn’t the sexiest thing I could’ve worn for our anniversary, but Chad was complimenting me all night long.

Ready for the best part? The dress was… drumroll, please… $5! The quality and the style to this dress made it worth every single penny. While the front is completely covered, there’s a little peek-a-book cutout in the back. Little details like this are my absolute favorites.

If you didn’t already know, I’m extremely short. I’m five foot even and my boyfriend is 6′ 6″, so I typically have to wear heels when we’re out. I wanted something that I was comfortable in though, so I paired it with the three inch platform Kaanas sandals. I have been head over heels for ever since they were sent to my doorstep, and they looked perfect with the look.

They might be high, but, because they’re flat, they are extremely comfortable. I had been waiting for the perfect time to wear them, but I think I’m going to start rocking them with jeans for everyday wear now too. The tan color makes them easy to dress up or down, and I love the woven details.

Of course, our date was about more than what I wore. We had a lovely night, just the two of us. He let me pick my favorite bottle of wine and shove different olive oil covered breads into his mouth to guess the flavor. We talked about everything from future plans to random questions, and it was beautiful.

After dinner, we stopped on our way out to have a photoshoot in the vineyards. He didn’t even complain once! I guess he really does love me hehe.

Now I don’t often talk about food on my blog, but my dinner was too good not to show you guys. Being gluten-free, it’s not everyday that I order a meal that I absolutely love. Normally, I don’t like paying for salads, but this was one heck of a meal.

I opted for the Greek Salad with salmon on top. It had olives and artichokes and goat chess. So pretty much everything that is good in the world. Plus is paired perfectly with the red wine we had. Oh, and it was huge! I swear it took me about an hour to finish, and normally I eat super fast.

We finished our night off at the place where it all began — our middle school. This is where we first met, so we went there spontaneously to go swing on the playground. Of course, we had to cut it short, so we got home in time for the Cavs game, but it was the perfect night.

Here’s a little video from the night. I can’t tell you when the last time was that I got pushed on a swing, and I was giggling like a little kid.

I hope you enjoyed the post as much as I did the night. What are your favorite date night spots and outfits? I’d love to hear all about it in the comments section!



  1. lifeofastayathomemom

    Very pretty dress 😊 date nights are the best! My boyfriend and I try to make sure at least once a month we have a date night and I get to wear a dress 😉 usual a nice dinner or at least something fancy enough to go with the dress😂

  2. K.M. Sutton

    This post gave me all the feels! What an incredibly sweet date night and your outfit was ah-may-zing! I love how you guys finished it! You are never to old to g singing on a playground! Happy anniversary! ❤

  3. lifeofangela

    Your giggles on the swing is the cutest thing ever!! You guys look like you had such an amazing time 😀
    That dress is gorgeous! I’m also a sucker for cute little details, that peek a boo section at the back brings the dress to another level ❤

  4. Dippy-Dotty Girl

    Ooh the dress is so pretty. But then with any ensemble, it is the wearer who makes the difference, so you do make it lovelier 🙂 It is amazing how a perfect date night is just all about the two people in it, isn’t it? You can do the silliest of things and have a blast x

  5. Lee

    You two are just adorable☺️💛 you looked beautiful, I like the dress and sandals. I’m in need of a wine day, but I’d love a date watching the sunset on the beach or in Paris or something lol

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