• About Jayme
  • Partnerships
  • Press
  • Shop My LTK
  • Contact
  • Nav Social Icons

  • Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer
  • All Blog Posts
  • Fashion
    • Spring & Summer
    • Fall & Winter
    • Lilly Pulitzer
  • Travel
    • Disney World
    • Disney Cruise
    • Disneyland
    • Palm Beach
    • Paris
    • Palm Beach Travel Guide
  • Lifestyle
    • Wedding Planning
    • Beauty
    • Fitness
    • Recipes
  • Home & Decor
    • Hosting & Parties
  • Gift Guides
  • About Jayme
  • Shop My LTK
  • Featured Press
  • Partnerships
  • Contact
  • Mobile Menu Widgets

    Connect

    Search

The Northern Prepster

The Northern Prepster

Lifestyle + Fashion Blogger | Pittsburgh, Palm Beach, and Disney World

  • Fashion
    • Spring & Summer
    • Fall & Winter
    • Lilly Pulitzer
  • Travel
    • Disney World
    • Disney Cruise
    • Disneyland
    • Paris
    • Palm Beach
    • Palm Beach Travel Guide
  • Lifestyle
    • Wedding Planning
    • Beauty
    • Fitness
    • Recipes
  • Home
    • Hosting & Parties
  • Gift Guides
  • All Posts

4 Looks for Valentine’s Day – Valentine’s Day Lookbook

February 11, 2019 · In: Fashion, Lifestyle

Hey y’all! Valentine’s Day is only a few days away and I’m starting to narrow down my outfit options. I put together this lookbook to hopefully give y’all some inspiration, no matter what your plans are for Valentine’s Day. I did 4 outfits, ranging from loungewear to cocktail hour appropriate. Let’s get into it!

1. Chill Valentine’s Day

This look is perfect for Valentine’s Day whether you’re having a movie night with the girls, lounging before getting ready for your date, or just having a cozy night in with your love. These pj pants from I Love Jewelry are so fun for this holiday. I got them as a part of their Monogram Swag Bag which is a monthly subscription that’s only $10! They also have a larger monogrammed monthly subscription for $21.95 a month called the MonoBox which includes even more fun monogrammed goodies. This month was my first month of both boxes, and I love it! My soft rose gold monogrammed sweatshirt is from Born To Be Sassy Boutique. They have so many fun, high-quality monogrammed products. So check out their website and their Instagram.

 

2. Cute But Casual

This look is keeping it casual with jeans, but is still feminine and cute. My bell sleeve top is from Legging Life and is SO soft, it feels like pajamas! My ripped jeans are from Francesca’s and super stretchy, which will come in handy eating all of those Valentine’s Day sweets 😉 These ones are a few years old and no longer sold, but here is a similar pair. My necklace was a Birthday gift from my parents and was perfect for Valentine’s Day since it features a bottle of champagne and two glasses. They got it from Kate Spade, but I unfortunately couldn’t find it online. Finally, my leather booties are from Madewell. I got these a few years ago and literally only paid around $8 for them… Yes, $8. They were originally over $200, on clearance for $10, and Madewell gives a student discount on top of sale. But here is a similar pair from Amazon. My purse is from Lilly Pulitzer and is no longer available, but here’s an option from Amazon. And finally, my earrings are from Forever 21.

 

3. Classy but Comfy

White jeans are the perfect in-between clothing item if jeans are too casual but a dress it too much. I struggled for years to find white jeans that fit me well. I struggle with jeans in general because my hips are wide, I have a flat butt, I have a small waist, and I have thicker thighs. But last summer I finally found a pair that fit me… From Walmart. Yes, Walmart. They by no means fit true to size (I had to get a size 8 and I’m a size 4), but they fit. They’re super stretchy as well, which I love. My top is from Lilly Pulitzer last year. And as for accessories my purse is from Kate Spade and my earrings are from BaubleBar (no longer available) but SugarFix (BaubleBar’s collection at Target) has a very similar pair! I also wore wedges to dress up this look a little as well. They’re an old pair from Target, but here’s a similar pair from Amazon.

 

4. Dressy Valentine

Finally, I have the most “dressy” look for Valentine’s Day. This is actually what I will be wearing! This Mila Shift from Lilly Pulitzer is in the print Hangin’ With My Boo. You may recognize it from my Birthday Haul video. But Grant actually got the matching men’s shorts, also from Lilly Pulitzer so we’ll be matching! He’ll probably just wear a polo to keep it casual, so I may add a white denim jacket if it’s cooler. My necklace is from Cora’s Den, and I’m wearing silver Jack Rogers. I’m also carrying a black Cynthia Rowley purse you may have seen in my Christmas haul.

 

So there you have it! I hope this post gave y’all a little bit of inspiration for what to wear this Valentine’s Day. Also comment down below what your plans are for the holiday whether it’s having some you time, hanging with girl friends, or having a romantic date with your love. Grant and I are going to dinner at Tony’s in Magic Kingdom, so excited! And let me know which outfit was your favorite 🙂

Thanks for reading!

xoxo

Jayme

Disclaimer: This is not a sponsored post. This post does include affiliate links that I am compensated for when an item is purchased. All opinions are my own.

By: Jayme · In: Fashion, Lifestyle · Tagged: buy me lilly, date night, fashion, Holiday, lilly pulitzer, ootd, outfit idea, outfit inspiration, outfits, Resort 365, Valentines day

you’ll also love

NEW Lilly Pulitzer Hearts Disney Collection
Spring Fashion Wish List
Valentine's Day Gift ideas. Valentine's Day gift guide.Best Valentine’s Day Gift Guide for 2025

Join the List

Stay up to date and receive the latest posts in your inbox.

Reader Interactions

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Next Post >

My Running Essentials – New YouTube Video!

Primary Sidebar

About Me

About Me

Hi there! My name is Jayme.

I love sharing my travels, fashion finds, and so much more here on my blog. You can expect a preppy, quiet luxury flair to my content. If that sounds something you're interested in - you're in the right place!

Thanks for coming on this journey with me!

Read More

Connect

join the list

Never miss a post! Sign up to receive updates and join my subscribers to see what's new!

Search

email me

hello@thenorthernprepster.com

Follow Along

@thenorthernprepster

It’s almost time for the U.S. Open!⛳️🏌️ It’s almost time for the U.S. Open!⛳️🏌️ Get all of your shopping done ahead of time this weekend by stopping at Oakmont CC between 10am-6pm - parking and entry are complimentary!🛍️ There is SO MUCH to choose from and we browsed for over an hour - such a neat experience.

#usopen #oakmontcountryclub #usopengolf #pittsburgh #pittsburghpa
MDW Camera Roll❤️🤳🏼 It’s definitely b MDW Camera Roll❤️🤳🏼

It’s definitely been a core memory weekend🫶🏼

#cameraroll #memorialdayweekend #longwoodgardens
Summer is calling my name this week🐚☀️ But Summer is calling my name this week🐚☀️

But with overcast skies, weather in the 60’s, and no vacations planned until the end of August - it’s hard to pick up the call😅

Let me know what your summer plans are👙

#trendingreelsaudio #trendingaudio #summer #summeraesthetic
I have a lot of new people here - hello & welcome👋🏼🌸

So I wanted to do a little post so yall can get to know me a bit better🤍 Whether you’ve been here a day, a week, a year, or 5+ years - thank you!🫶🏼

#classicfashion #gettoknowme #discoverpage
While we didn’t have the best beach weather last While we didn’t have the best beach weather last weekend, we still managed to soak up some sun☀️🌊

The best part of any beach trip is showering after a long day in the water and throwing on your favorite sun dress with your fresh tan🤍 I am obsessed with this new one I snagged for only $35 - plus the perfect purse to match🐚

Comment SHOP for outfit info🤍
https://liketk.it/5dGbZ

#summerfashioninspo #beachoutfit #targetstyle #ltksummer
Me Being Born & Bred in the North🤝Me Dressing L Me Being Born & Bred in the North🤝Me Dressing Like Someone From the South

Genuinely if I have $1 for every time I’ve been told I “don’t belong in Western PA” - I’d have enough money to move to the southern city of my choosing😂 But seriously - I’ve gotten these comments since I was in middle school! 

I’ve heard it said PA is 10 years behind on fashion👀 I can confirm people don’t understand me or my Lorna Murray hat I bought back in 2022👒

#classicfashion #piperno #thewhitelotus #preppyfashion #fashionreelcreator

As Seen On

National Geographic TODAY Palm Beach Illustrated NBC News

Footer

On the Blog

  • Fashion
  • Travel
  • Lifestyle
  • Wedding Planning

More

  • About Jayme
  • Partnerships
  • Featured Press
  • Shop My LTK

Copyright © 2025 · All Rights Reserved.