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

April 15, 2026April 15, 2026

thepinkchickadeeLeave a comment

What I Wore To Work – December 2025

Like many of the Winter months, I gravitated towards LOTS of cozy vibes and sets during my December 2025 work from home days. I also had a few holiday events and parties after work some evenings, where I found myself wanting to be more comfortable during the work day and more dressy during the evening. To tie it all up with a bow, December 2025 was a FREEZING time in the Washington, DC area like many other parts of the United States. That all being said, cozy looks were for the win this past working month!

*Disclaimer: Please note that this post 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 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.

Shop it here! And sweatshirt from J Crew Factory.

Shop it here!

***Forgot to link***

Shop it here!

XOXO – Katie <3

January 1, 2026January 27, 2026

thepinkchickadeeLeave a comment

What I Wore Out Of Office – December 2025

Having completed my first full month wearing + styling jeans in over 10 years, a month filled with soooo many tartan OOTDs, and so much sparkle in between it all, December truly is one of my favorite months to style looks for! Personally like years’ past, I find myself gravitating towards exclusively my tartan pieces within my wardrobe throughout the month of December. The tartan outfits did not disappoint and, as always, it was fun to style them in 2025. This year, I took a fun week off of work and went to Philadelphia for 4 days to visit friends and enjoy ALLL the Christmas fun what I like to call the City of Sisterly Love. At the same time, I enjoyed all of the holiday fun whether it be close to home or in Delaware with my Dad. All in all, I enjoyed ALLL the fun outfits last month!

*Disclaimer: Please note that this post 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.

Shop it here!

***Forgot to link***

Shop it here!

***Forgot to link***

XOXO – Katie <3

January 1, 2026January 27, 2026

thepinkchickadeeLeave a comment

What I Wore To Work – November 2025

I feel like every November I start wearing more sweats and lounge wear as it starts to get colder outside. And, hence, my work wear becomes filled with lots of cozy lounge wear looks and less dressy looks, as it’s usually freezing and I just want to be cozy!! Clearly, November 2025 was NO different than any other November – LOL!

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

Shop it here!

***Forgot to link***

Shop it here!

XOXO – Katie <3

December 3, 2025January 27, 2026

thepinkchickadeeLeave a comment

What I Wore Out Of Office – November 2025

From two weekends away to Charlotte (see my guide on Charlotte here) and Raleigh (see my guide on Raleigh’s North Hills here), a wonderful family and Christmas-filled Thanksgiving weekend, another Friendsgiving hosted (see my tablescape here), and a visit to the Southern Living Idea House (more to come on that *very* soon!), SO much has happened during November 2025. In fact, November has been one of my favorite months of 2025!! I know a lot of us have found this year to be a bit chaotic nevertheless, so I was so grateful to have a really great month in 2025!! At the same time, I am also psyched to share what I wore as I had TONS of fun putting together my outfits throughout this ultra-fun month. Now, let’s get into what I wore out of office in November 2025!

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

Shop it here!

***Forgot to link***

Shop it here!

***Forgot to Link***

***Forgot to link***

Shop it here!

***Forgot to link***

Shop it here!

XOXO – Katie <3

December 3, 2025January 27, 2026

thepinkchickadeeLeave a comment

What I Wore To Work – October 2025

From Back to Work in September 2025, October 2025 has been the full fledged kick off of the Fall fashion season for me! I have truly loved getting to style some super fun Fall outfits this past month. Fall/Winter fashion is, indeed, my favorite to style for, too!

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

Shop it here!

XOXO – Katie <3

November 5, 2025January 27, 2026

thepinkchickadeeLeave a comment

What I Wore To Work – September 2025

As I briefly mentioned in my most recent Life of Katie post, I enjoyed kicking off my Back to Work OOTD series over on Instagram (let’s be friends @_thepinkchickadee) after my week in Rome, Italy (here)! I’ve actually been excited to start styling Back to Work OOTDs since earlier this Summer. As a kid and teenager especially, I LOVED Back to School outfits the most. I guess some things never change!

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

Tap to Shop

XOXO – Katie <3

October 2, 2025January 27, 2026

thepinkchickadeeLeave a comment

What I Wore Out Of Office – July 2025

A long weekend in Delaware, a morning at the museum, a few Sunday mornings at church, and several outings close to home, oh my! Nevertheless, July 2025 was a great month out of the office.

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

Tap to Shop

***Forgot to link***

Tap to Shop

***Forgot to link***

Tap to Shop

XOXO – Katie <3

August 6, 2025January 27, 2026

thepinkchickadeeLeave a comment

What I Wore To Work – July 2025

From networking events in the office and at Nationals Park to a few jam-packed days working from the beach, July 2025 truly was a busy working month! These Summer months pretty much *everywhere* have been so so so hot and humid aka “swamp season.” However, through it all, I have been striving to make the best of it all and savor up every moment of Summer time, whether professionally or personally.

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

***Forgot to link***

Tap to Shop

XOXO – Katie <3

August 5, 2025January 27, 2026

thepinkchickadeeLeave a comment

What I Wore Out Of Office – May 2025

As previously mentioned in my work outfits blog post for this month (here), May 2025 was filled with plenty of showers here in the Washington, DC area! Nevertheless, I found myself enjoying more cozy nights in than out this past month. At the same time, I have been striving to savor my weeknights in as opposed to going out on the town with a few exceptions here and there. I find this balance between staying in and going out to be great for my mental health as well as my overall wellness.

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