Preppy Party Outfits

I know I feel like this every year, but I just can’t believe how busy we suddenly are now that the holidays are upon us! I’m really loving it this year. Last year, the holidays were a challenge for a number of reasons and then I’d go so far as to say that this hasn’t been our #1 year in general. With that said, it is making me appreciate the holidays and the holiday spirit so very much. I’m feeling eternally grateful for my loved ones and so inspired + cheery thanks to the holidays that I find myself saying yes to everything.

Not only am I RSVPing yes, but I’m finding myself feeling genuinely excited for everything when the time comes. I’ve been getting dressed up quite a bit so I wanted to share some preppy party outfits with y’all in case you are shopping for a packed holiday party circuit. It’s the holiday season right now so I included preppy party outfits for the holidays below. But I plan to come in and add to this post throughout the year with prepster inspired party outfits for all kinds of occasions. So, if you identify with preppy style, then you’ll love these preppy outfits. Enjoy!

Dress (c/o) / Boots / Purse / Scarf (similar, similar)

Preppy Party Outfits

Friendsgiving

I love the featured outfit of this post so much for Friendsgiving. We went to a wonderful Friendsgiving this past weekend full of great company, delicious food, and fun games. I know a lot of y’all are heading to Friendsgivings this coming weekend so this outfit is for you! I love this navy blue dress even more than I thought I would. It looks adorable online but it wears so well!

I often buy more of the printed Gal Meets Glam pieces (as seen here and here) but I have to say that this might be my favorite GMG piece I’ve gotten. And I highly recommend it! I picked it up from new-to-me shop navyBLEU; an online boutique curated of all things, you guessed it, navy blue! Isn’t that just the cutest concept!? The shop includes well-known brands such as Gal Meets Glam, Joules, Draper James, Sail to Sable and more! NavyBLEU also carries is flowy dotty GMG navy dress, which is a cute preppy party dress perfect for gatherings with family.

P.S. use code friends2019 for 30% off your order at navyBLEU! You can snag my dress at a major discount!

I completed this outfit with beautiful brown accessories. I was on the lookout for an affordable pair of knee-high brown suede boots because I always wanted to reach for such a boot in my closet. But I didn’t have a pair. So I was so happy when I discovered these beautiful suede chestnut boots! These boots look really high-end but they are only $170 and the quality is wonderful so far. They are crafted in luxe, goes-with-everything suede with a really comfortable block heel. They are great paired with jeans and dresses! Lastly, I love the woven leather Dragon Diffusion purse that I scooped up this summer in Jackson Hole. I carry it for everyday use non-stop. I truly would tell anyone to buy this purse now. You won’t regret it! I think both accessories are classics that complete this preppy look.

Friend’s Festive Birthday

Jean and a cute tee is my recipe for success when it comes to dressing for an occasion like a friend’s birthday. During the holidays, I will try to make my outfit a touch festive, which is why I love a bold red top for such a party. Slipping into a pair of red ballet flats to complete the tone on tone look is preppy style at its best. P.S. doesn’t Maybelle look like the cutest preppy girl with her plaid bandana!?

Top (old – similar, similar, similar, similar) / Jeans / Flats (old – similar, similar) / Purse (similar for less: one, two) / Maybelle’s Bandana (25% off!)

Holiday Party

A timeless and classically preppy party dress is a little black dress. A little black dress will never ever fail you. So when in doubt, wear a little black dress to a holiday party. I think any preppy woman will love the vibe of my little black dress because the cap sleeves scream prepster to me. It’s all in the details! Here are some dress ideas to snag the look: one, two, three, four, five, six, seven.

Dress (similar – one, two, three, four, five, six, seven) / Clutch (sold out – similar, similar) / Earrings (old – similar) / Necklace (similar) / Heels (old – similar, similar)

Office Christmas

Who has an office Christmas party this year!? If so, I have two outfit recommendations for you that are perfect. They are on the more casual side so if your work party is dressier, then maybe consider the above black dress. However, the below green dress and sweater dress are great for your average office Christmas party. Both dresses are from last year but I linked a few other similar options. Holiday preppy clothes for everyone, ha!

Outfit 1: Sweater Dress (old, similar: one, two, three, four, five, six) / Cap Toe Slingbacks

Outfit 2: Green Dress (old, similar: one, two, three, four, five) / Earrings / Clutch (sold out – similar, similar)

Preppy Winter Wedding Outfit

When it comes to preppy winter wedding outfit ideas, I love to go with a classic silhouette that is embellished with some holiday sparkle. This pearl-embellished dress is a perfect option! It is old but I found a few similar options for y’all below that are embellished with pearls, embroidery, sequins, and other sparkle.

Dress (old, similar: one, two, three, four, five, six, seven, eight, nine, ten) / Purse (old, similar: one, two, three) / Shoes (old, similar: one, two, three)

For all my preppy readers, I hope you found this post helpful! xx

Dress (c/o) / Boots / Purse / Scarf (similar, similar)

Photography by Edwin Eversole