Preppy Outfits Diaries – March 2026

Long time, NO outfit diaries! In personal news, I have made the switch to self-employment in January 2026 and have been a bit busy with mapping out my strategy for the year amidst my career change. Nevertheless, I’m excited to share some preppy outfits diaries on a monthly basis!  

*Disclaimer: Please note that this page contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own. Thank you for supporting The Pink Chickadee.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page. For my outfit archive, look no further than My Preppy Outfits Archive.

Preppy Outfits Diaries – March 2026

My Favorite Pieces

This section will focus on my favorite pieces worn each month, which includes my favorite travel shoe & quilted jacket.

My Outfits 

Here’s to many more outfits to come!

XOXO – Katie <3

What I Wore to Work: May & June 2023

If you don’t already follow me on Instagram (follow me @_thepinkchickadee!!), you likely aren’t well aware that halfway through the month of May, I started sharing my work outfits on my Instagram (and also Facebook) stories. As I wrap up my June work month *just a bit earlier than usual* due to a much-needed beach week in South Carolina with some of my very best friends, I am filled with so much gratitude for deciding to share my work outfits here on this incredible platform. It has truly become such a highlight of mine to be able to share my work outfits with y’all. I *even* shared that I am sharing my work outfits with y’all on my LinkedIn of ALL places – LOL!

Back story: when I was in high school, it became such a highlight of mine to plan out my outfits the night beforehand, especially as my days became CONSUMED with AP course work, SAT prep, college applications, and extracurriculars aka the typical high school student life of an over-achiever like myself. Outfits were THE highlight of my high school years. I *even* had a blog where I literally just posted my outfits my Senior year of high school (like 2016!) called Katie’s Closet Blog! Then, into college, I began dressing a bit more casual as I LOVED getting to sleep in aka THE college lifestyle. And, then, COVID-19 hit at the end of my Junior year of college, which meant slumber wear all day every day with the exception of a few days here and there. This whole casual dress attire of mine continued into my post-graduate years with the work from home lifestyle. I actually used to HATE work from home, due to the fact that I missed getting to dress up in a cute outfit around others everyday. However, in recent months I have grown to LOVE the primarily work from home lifestyle, as I have so much freedom and flexibility and no commute within my day to day routine. BUT, I was missing getting to showcase my super cute outfits.

Innovate is the word for my work from home outfits. Innovate is ALSO one of the biggest key words of my company in the ways that its growing. As crazy as it seems, innovate is a word that I LOVE and see as key to my personal life in so many different ways. So, yes, innovation is what allows me to share my outfits with y’all without feeling like I am missing out on doing so in my day to day life. The highlight of my high school days, which kept me going throughout those loooonggg days of essentially prepping for college, now keep me going in my postgraduate life.

I decided to combine my May and June work outfits into one blog post, due to starting sharing my May work outfits in the middle of the month and going on vacation the last 7 work days of June. I have recently gotten away from sharing outfits via the Shop LTK platform, as I want my looks to solely serve as inspiration from one’s own closet, rather than a place to simply impose consumerism when it may not be right for others. Any how, I hope you enjoy!

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page.

Dress: Draper James; Sandals: Jack Rogers x Vera Bradley (old collab); Earrings: Small Boutique in Charlotte, North Carolina (forget the name of it!); Bracelets: Amazon & All She Wrote Notes
Dress: Lisa Fernandez x Target (old collaboration); Cardigan: Northern Isles; Sandals: Jack Rogers; Handbag: Lilly Pulitzer; Bracelets: The Inspiration Co. & Amazon
Top: Lilly Pulitzer; Skirt: Talbots; Headband: The Pioneer Woman at Walmart; Necklace: Talbots; Bracelets: Amazon & All She Wrote Notes
Top: Hawthorn; Pants: Talbots; Necklace: Thrifted ; Bracelets: Amazon
Dress: Crown & Ivy at Belk; Pearls: Thrifted; Scarf: Tommy Hilfiger; Headband: J Crew Factory; Sandals: Jack Rogers; Bracelets: Kendra Scott, Amazon, & Little Words Project
Dress: Lilly Pulitzer; Handbag: Kate Spade; Flats: DSW; Bracelets: Amazon, The Inspiration Co., & Kendra Scott
Dress: Gretchen Scott; Bracelets & Earrings: All She Wrote Notes
Button-Down: Karl Lagerfeld; Pants: Talbots
Tee & Skirt: Vineyard Vines; Headband: Lilly Pulitzer; Bracelets: Teleties x Scout Bags; Sandals: Sperry; Earrings: Cora’s Den
Dress: Lilly Pulitzer; Cardigan: Crown & Ivy; Headband: Anthropologie
Dress: Amazon; Button Down: Ralph Lauren; Bracelets: The Inspiration Co. & All She Wrote Notes
Tee: Lilly Pulitzer; Skirt: J. Crew; Headband: Lilly Pulitzer x Lele Sadoughi (old collab); Necklace: Nordstrom Rack; Bracelets: All She Wrote Notes
Dress: Lilly Pulitzer; Bracelets: Amazon & All She Wrote Notes
Dress: Target; Headband: Scout Bags; Bracelets: Kendra Scott & Amazon; Earrings: SugarFix from Target
Tank: Lilly Pulitzer; Skirt: Banana Republic; Bracelets: Kendra Scott, Amazon, & Little Words Project
Dress: Jude Connally; Bracelets: Teleties x Scout Bags hair ties
Tank: Walmart; Necklace: Thrifted; Skirt: Elie Tahari; Bracelets: Kendra Scott & The Inspiration Co.
Tank: Fabletics; Skort: Thrifted; Bracelets: Teleties x Scout Bags hair ties
Dress: Lilly Pulitzer; Headband: J Crew Factory; Earrings: Found On Madison; Bracelets: Amazon & The Inspiration Co
Top & Pants & Headband: Lilly Pulitzer; Sandals: Sperry; Jacket: Lands End; Bracelets: Amazon, J Crew Factory, & The Inspiration Co
Dress: Crown & Ivy at Belk; Bracelets: Kendra Scott, The Inspiration Co, & Amazon

Stay tuned for my July work outfits in *just* a month!!!

XOXO – Katie <3