How To Wear Lilly Pulitzer At Work (From A Former Corporate Girly!)

***Please note that this How To Wear Lilly Pulitzer At Work (From A Former Corporate Girly!) guide will be updated and recirculated periodically to reflect the most up-to-date information. This shopping guide was most recently updated as of August 2026.***

During my latter years of college and pre-workforce days, the idea that Lilly Pulitzer attire was not meant to be worn in the workplace was very much emphasized. Unless you worked at a Lilly Pulitzer boutique and had a business casual dress code, the idea that you are to wear bright and colorful attire such as the likes of Lilly Pulitzer felt very taboo. Well, that idea of wearing Lilly Pulitzer in the workplace felt very taboo to those that were around me. However, ever since I’ve been in the workforce since July 2021, I have seen the benefits to embracing one’s personal style in the workplace *even* if that consists of bright colors and wearing Lilly Pulitzer at work.

This guide will focus on how to wear Lilly Pulitzer at work (from a former corporate employee’s perspective!).

*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.*

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

If you also love Lilly Pulitzer and its other brands like it, including boutiques like Avara, brands like Bodenbrands like Sezanebrands like Ralph Laurenbrands like Tommy Bahamastores like Williams Sonomabrands like Ted Bakerstores like ban.dostores like Kohl’sbrands like Vera Bradleybrands like Betsey Johnsonbrands like Southern Tidebrands like Vineyard Vinesbrands like Tory Burchbrands like Farm Riobrands like J Crewbrands like Banana Republicbrands like Talbotsbrands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck guides.

If you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazonwhere to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

For *even* more preppy style inspiration including brands like Lilly Pulitzer, then check out my Lilly Pulitzer Signature Stores master listpreppy clothing brands listpreppy clothes style guide, and styling preppy outfits guide.

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

How To Wear Lilly Pulitzer At Work

How To Wear Lilly Pulitzer At Work (From A Former Corporate Girly!)

Believe it or there are several different ways to wear Lilly Pulitzer at work! From my personal experience, it was really fun to style several outfits for the office within the parameters of a business/business casual dress code. Below, I have listed my personal tips for how to wear Lilly Pulizer at work:

  • Let your Lilly Pulitzer do all of the shining! Lilly Pulitzer pieces are primarily bright. Try to make the Lilly Pulitzer pieces that you wear the biggest statement of your outfit. And pair it with neutral/Navy separates. 
  • Invest in a go-to pair or a few pairs of flats for the office to wear with your Lilly Pulitzer and your work wear rotation. Tan, white, black/white, or even a blush Pink/rose gold will certainly do the trick!
  • As for jewelry, I recommend investing in a few dainty, simple pieces that embody your personal style. I always suggest styling a pair of stud earrings for the office. Personally, I love Kendra Scott’s pieces!
  • For cooler office air conditioned rooms or cooler days outside, I recommend packing a solid cardigan or wearing a solid blazer, lady cardigan (which has become popular!), or trench coat to the office.
  • Most importantly, don’t be afraid to HAVE FUN and always be true to you!!!

Pink Chickadee posing inside a life-size pink Barbie photo box

What Lilly Pulitzer To Wear At Work

Lilly Pulitzer Nadine ChillyLilly Dress

From my days as a corporate girly: Yes, there have been several occasions that I’ve worn Lilly Pulitzer to the office. I do have a few favorite pieces that I adore specifically for those workday occasions. My favorite go-to Lilly Pulitzer workwear piece is the Elsa top, which I have worn for company promotional events and videos (and gotten several compliments on from women in my own company’s leadership, too!). At the same time, I adore wearing a Lilly Pulitzer printed dress (not too revealing) with a pair of neutral flats/heels, a cardigan/blazer, and accessories, too. In fact, I’ve worn a bright pink Lilly Pulitzer shift for my company headshot! Needless to say, I’m a firm believer that if styled appropriately for your office’s dress code, you can wear Lilly Pulitzer to the office.

In fact, Lilly Pulitzer has a Work Clothes section on their website that has the most up-to-date pieces fit for the office! Shop Lilly Pulitzer work clothes here.

What To Wear With Lilly Pulitzer At Work

pink and green printed top paired with dark skinny jeans and green embellished flats

As someone who tended to wear LOTS of Lilly Pulitzer at work during my corporate girly days, I always air on the side of styling neutral/solid pieces when wearing my favorite resort wear brand. I suggest investing in a few versatile pieces you can wear often, especially when styling vibrant Lilly Pulitzer pieces. My go-to work bag is a Barrington Gifts personalized tote and my go-to work shoes are Tory Burch Minnie flats.

Wrap-Up:

How To Wear Lilly Pulitzer At Work

From company-sponsored conferences to company videos, events, and symposiums when I was working in corporate, Lilly Pulitzer has truly been the one constant within my wardrobe at each occasion. Unlike my fears of having to reevaluate my love of Lilly Pulitzer and desires for entering the corporate world post-graduation from college, I am so glad that those fears have since been debunked. If only 21 year old Katie could see herself during those days!!

XOXO – Katie <3

Preppy Outfits Diaries – July 2026

From a week in Delaware to America250 festivities back at home and a few days in Wilmington, North Carolina, July 2026 as I always say was definitely a memorable one for the books! Personally, I LOVED wearing some fun patriotic and Americana outfits early in July while ending the month wearing lots of pink (as per usual!). The hotter summer temperatures in the Washington, DC area are really draining me, so I’m looking forward to the cooler days of fall. In the meantime, I’m making the most of summer while it’s here. This August, I have 3 weekends away with friends (one for a wedding!) in North Carolina and am excited to share what I wear – preppy outfits edition – for those occasions, too!

*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.

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

   

My Favorite Pieces

Honestly, this July 2026, many of my preppy outfits involved LOTS of Lilly Pulitzer, my go-to Sperry flip flops or Jack Rogers sandals, and two-piece lounge sets that look dressier than they are comfortable! 

My Outfits

preppy floral midi skirt and a high-end designer tote bag

blue geometric-patterned sleeveless dress accessorized with a black and white woven straw crescent handbag

white Old Navy flag graphic t-shirt

preppy classic smocked midi dress with an eye-catching textured woven bag

bright green swimsuit with a colorful patterned sarong and a hot pink crochet hat

Lilly Pulitzer Riegan Sleeveless Polo Dress

preppy green floral print tunic dress with pink contrast elements

sleeveless polo-style dress with a ruffled hem

sleeveless blue and white floral mini shift dress

Lilly Pulitzer Analeese Midi Dress

preppy black mini dress and Louis Vuitton bag

preppy black and white striped T-shirt dress

pink and white striped seersucker two-piece shorts set paired with a distinctive black and cream two-tone woven half-moon straw tote bag

Lilly Pulitzer Mila Stretch Shift Dress

preppy floral printed mini A-line skirt

Lilly Pulitzer Gone Coastal Dress

green floral maxi preppy dress with ruffle straps, paired with a brown Louis Vuitton tote bag

Lilly Pulitzer sleeveless dress

preppy outfit featuring a white halter top, blue-and-white patterned wide-leg pants, a turquoise necklace, and sandals

blue and white gingham matching set

light blue tiered maxi preppy dress featuring ruffle straps and a smocked bodice

black-and-white gingham dress with balloon sleeves, a colorful neck scarf, and tan heels while holding a vibrant pink leather purse

matching pattern preppy dress and a custom embroidered bag

preppy outfit featuring a blue-and-white botanical print shirt dress with a white belt, holding a brown bag

pink floral maxi dress featuring a smocked bust and spaghetti straps

Lilly Pulitzer Bessie Skort

pink gingham sleeveless two-piece set for a preppy outfit

Roller Rabbit x Target bouquet long sleeve tie-neck boho top and carrying a Louis Vuitton Neverfull handbag

Here’s to styling more Summer outfits for the dog days of Summer!

XOXO – Katie <3

Shopping in Charleston, South Carolina Guide

***Please note that this Shopping in Charleston, South Carolina Guide will be updated and recirculated periodically to reflect the most up-to-date information. This travel guide was most recently updated as of April 2026.***

While many people view New York City as THE American fashion capital, I have ALWAYS fallen more and more in love with the fashion sense and Southern charm that comes with the style in *surprise* Charleston, South Carolina. I have ALWAYS admired the gorgeous preppy and Southern flair style and Charleston seems to have ALL the boutiques which I have dreamed of visiting in-person yet were too far from my Washington, DC area home base to do so. Just a few weeks ago, my best friends and I had a fun beach weekend in Isle of Palms, South Carolina (here) aka one of the prettiest places I have ever been (!!!) where we spent a day in Charleston (here). On THE top of my list of things to do in Charleston …. check out ALLL the shops. SO, I am sharing my own curated guide to shopping in Charleston, South Carolina!

*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 United States travel inspiration, check out my Exploring 50 States expedition page.

Shopping in Charleston, South Carolina Guide

From Madison Mathews to Lilly Pulitzer to LoveShackFancy, the charming fashion and shopping in Charleston, South Carolina is HARD to beat! Luckily for myself, the shops in Charleston’s Fashion District are primarily on the well-known King Street or within a few blocks away, making it an easy and fun afternoon activity. There’s *even* a Gucci and Louis Vuitton storefront there, too. A Target aka my favorite storefront is on King Street as well. Needless to say, I had an incredible time shopping and mostly browsing here in Charleston. And, I think YOU will have a great time shopping in Charleston, South Carolina, too!

  • Gretchen Scott Designs (233 King Street) – Living by the motto “Laugh More, Gripe Less, Ignore Critics, Say Yes, Order Dessert, Love Life,” Gretchen Scott Designs’ founder and CEO Gretchen Scott specializes in super fun, chic, and globally-inspired designs often in a bright and bubbly fashion. Shop Gretchen Scott Designs online here.
  • Candlefish (270 King Street) – The ultimate destination for an array of candles and gifts including storefront workshops, Candlefish has a library of over 100 scents to choose from of which will be perfect for your happy home. Shop Candlefish online here.
  • Kenny Flowers (345 King Street) – With products crafted in Colombia and Bali, Kenny Flowers specializes in beautifully made tropical apparel and goods, including an array of Hawaiian shirts and resort wear. Shop Kenny Flowers online here.
  • Stoney Clover Lane (316 King Street Suite A) – Selling customizable and personalized nylon or leather accessories including bags and pouches in a range of colors, Stoney Clover Lane truly has it all. The best part?!?! Customers can get their pieces customized at the store! Shop Stoney Clover Lane online here.
  • Hill House Home (145 King Street) – Founded in 2016 by London native and New York living Nell Diamond, Hill House Home brings romantic and dreamy styles through Diamond’s dream to make “happy things for happy places.” Hill House Home’s most well-known garment is their Nap Dress, which I have created both a Nap Dress review for here and a Nap Dress dupe shopping guide for here. Shop Hill House Home online here.
  • Roller Rabbit (163 King Street) – With pop-up storefronts across the country including recently in Washington, DC’s Georgetown, Roller Rabbit is a feel-good lifestyle brand known for their popular printed pajamas, loungewear, clothing, home goods, and accessories. Shop Roller Rabbit online here.
  • Madison Mathews (178 King Street) – I have been following Madison Mathews on Instagram for a few years now and have fallen IN LOVE with the brand’s gorgeous designs. I stopped in here to kick off my shopping stroll on Charleston’s King Street while my friends went in mainly for the air conditioning and free seating LOL! I LOVED finally getting to admire some of the most stunning designs by Madison Mathews in-person after seeing them on my phone screen for the past few years. The BEST part?! The store owners had their gorgeous dog there who LOVED visiting with me and my sweet crew (!!!). Shop Madison Mathews online here.
  • Palm Avenue (251 King Street)Palm Avenue is a Lilly Pulitzer Signature Store that was once one of 4 storefronts across the South. Now, Palm Avenue’s Charleston location remains the only storefront still in business since their Savannah and Raleigh locations went out of business. The ladies at Palm Avenue were SO SWEET and welcoming and *even* had a preview of Lilly Pulitzer’s Splash Sale on their sale racks! I invested in one of their hot pink belt bags for summer walks with my dog Rosie. My fellow Lilly Pulitzer loving best friend Alanna and I had a blast there!
  • Spartina 449 (231 King Street) – For YEARS, I have been a HUGE fan of Spartina 449‘s designs. More speciafically speaking, I am a HUGE fan of the Lowcountry-based design house’s map prints on their accessories of which I own items in the Chesapeake Bay and Virginia map prints. It was SO MUCH FUN to stop in one of my favorite brand’s storefronts that are not super common up in the Washington, DC area. Not to mention, the ladies there were so sweet. Shop Spartina 449 online here.
  • The Finicky Filly (303 King Street) – Confession: I do not know much about The Finicky Filly besides the fact that one of my college friend’s Mom’s suggested it to me. HOWEVER, the name is WAYYYYY too cute not to pop in and make a visit at the next time I am in town. Shop The Finicky Filly online here.
  • LoveShackFancy (218 King Street) – Well, I rarely feel like a 5 year old kid in a candy store nowadays, BUT I did when I stepped foot into THE iconic LoveShackFancy storefront here on Charleston’s King Street. The LoveShackFancy storefront is literally every grand millennial’s (like myself) dream come true in a store. I was so so so obsessed with the storefront the entire time and my friends LOVED all the sparse and plethora of seating options within the air conditioning *yet again*. The ladies working at LoveShackFancy were SO SWEET, too, and were happy with my excitement within their store. The day we went, an artist was custom painting on sunglasses cases which was complimentary with a purchase of one as apart of a promotion going on then. Needless to say, the vibes there were impeccable. Truly, a DREAM COME TRUE (!!!). Shop LoveShackFancy online here.
  • Charleston City Market (188 Meeting Street) – While it can get pretty overwhelming to walk through ALL the shops, the Charleston City Market has been apart of the city dating ALLLL the way back to the 1790’s. It also stretches four blocks of Charleston’s historic district and has markets of local businesses to Charleston, Charleston-oriented souvenirs, and small business owners. I ended up purchasing two of Sofya’s (here) stunning paintings to frame in my own apartment. (I hope to buy more of her designs someday, too!).
  • Old Whaling Company (409 King Street Suite 100) – We stopped here *also* for the air conditioning – surprise!! BUT, we all LOVED getting to smell the plethora of lotions, body soap, and candles that Old Whaling Company has to offer its customers. Maybe, *just maybe*, I will be placing an online order soon after I write this paragraph. Old Whaling Company also has a mini storefront at the Charleston City Market AND a gorgeous mural of sea-like paintings on its walls within its King Street store. Shop Old Whaling Company online here.
  • Jean-Pierre Klifa (214 King Street) – As of Summer 2023, the Jean-Pierre Kilfa storefront is brand-new to Charleston! I ended up talking with the store associate who was SO SWEET and explained the fashion house’s brand-new ties to Charleston. The Jean-Pierre Klifa brand is *just like* an affordable version of Emilio Pucci’s gorgeous designs with the bright and bubbly charm that comes about from Lilly Pulitzer. I had a blast browsing the new storefront and congratulating the associates there! Shop Jean-Pierre Klifa online here.
  • Lake Pajamas (153 King Street) – I have seen SOOOO many of my fellow blogger/influencer friends raving about Lake Pajamas. I once found a pair of Lake Pajamas at my local Goodwill and sadly did not pick them up for some reason (there’s always a next time, though!). One day, I shall own a pair. And, next time I am in Charleston, I *most definitely* want to make a stop in this sleeping in heaven storefront! Shop Lake Pajamas online here.
  • The Tiny Tassel (46 Spring Street Unit B) – I have been connected to The Tiny Tassel’s store owner the ultra-adorable Mimi for a few years now and have been DYING to check out her stunning storefront for a few years now! I LOVE LOVE LOVE the designs that Mimi designs herself, ranging from beaded earrings and bracelets to clothing. I’ve had a pair of flamingo tassel earrings for over 3 years now! Well, what can I say?! There’s ALWAYS a next time!! Shop The Tiny Tassel online here.

Wrap-Up

The shopping alone would bring me back to Charleston just about *any* day. I will definitely be back in Charleston (hopefully) very very very soon!!

XOXO – Katie <3

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!

*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.*

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

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XOXO – Katie <3

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!

*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.*

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

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XOXO – Katie <3

What I Wore Out Of Office – October 2025

From a vineyard visit to kick off the month to a family dinner party to day trips around the Washington, DC area (and beyond!) and a night out at the ballet and some lounging in between, October 2025 was truly one for the books! I have found in recent years, October to be such a great month filled with sooooo many memories. I like to think that it’s because October is the kick off to Fall. SOOOO many memories were made like in past Octobers this October 2025. And, my outfits were the perfect way to commemorate another great October!

*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.*

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

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XOXO – Katie <3

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!

*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.*

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

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XOXO – Katie <3

Preppy Fashion Lover Gifts Guide

***Please note that this Preppy Fashion Lover Gifts Guide will be updated and recirculated periodically to reflect the most up-to-date information. This gift guide was most recently updated as of October 2025.***

Lilly Pulitzer, Vineyard Vines, J Crew, and Kate Spade, OH MY! As a self-proclaimed preppy fashion lover and grand millennial, I could not share some preppy fashion lover items for my Christmas Gift Guides. Today, I am rounding up all of the preppy fashion lover gift ideas to complete your preppy fashion wardrobe and for your preppy fashion lovers in your life all while at different price points. In the case that you’re interested in some of my other preppy fashion shopping guides, then look no further than my blog posts on a few brands to know like Lilly Pulitzer, Printfresh Pajamas Review, Hill House Nap Dress Dupe Shopping Guide, and more. Happy shopping!!!

*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 opinionInterested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!  s are my own.*

 

Preppy Fashion Lover Gifts Guide

This Preppy Fashion Lover Gifts Guide will be divided into 5 sections based on price point: $25 and Under, $50 and Under, $100 and Under, $200 and Under, and $200+. That way, there’s a gift every preppy fashion lover in mind!

$25 and Under

$50 and Under

$100 and Under

$200 and Under

$200+

Happy holidays and happy shopping, preppies!

XOXO – Katie <3

What I Wore Out Of Office – September 2025

When putting together this post, my first thought was: “damn I wore a lot of cuties!” LOLL! The month of September’s fashion at the intersection of Summer and Fall fashion is such a fun one. From pumpkin patches to brunches and dinners with friends including my first annual Harvest Dinner Party, September 2025 out of office was such a fun one.

*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.*

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

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XOXO – Katie <3

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!

*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.*

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

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XOXO – Katie <3