The Best 10 Preppy Dresses For Work and the Office

Chic and Timeless Office Outfits
Tuckernuck Tartan Dress

If you’ve scrolled through my LTK or Instagram pages, you know that I appreciate a preppy outfit for work! I love how the defining characteristics of preppy style are “clean” and “understated” with a dash of high-end sophistication. Each look is tailored and timeless with a girl next door twist. For someone like me who loves color and structure, the preppy style lets me experiment freely with both bold finds and neutral masterpieces. 

Now, I admit, sometimes I go way past preppy into avant-garde, but as a full-time workfluencer, I need refined and chic pieces for the office that still feel like me. So, preppy is the way to go! Today, I am sharing some workwear looks that are preppy . . . but have a tinge of Style Charade whimsy. Here are some of my fave looks:

Tuckernuck Tweed Dress

10 Preppy Dresses For Work

Tweed Bow Dress Workwear Look

This Tuckernuck tweed bow dress is perfect for a chic, preppy workwear look, because it has the essence of a blazer or suit jacket (even down to the bowtie!), but it’s looser structured and more feminine. It comes in three different colors and patterns: light blue, jacquard, and tan. So, Tuckernuck has a little something for everyone, whether you’re a color queen, print princess, or neutral noble. 

To style it, wear gold bow heels and a few pieces of simple gold jewelry. Sunglasses add good contrast to prevent it from looking too buttoned-up. Finally, add your favorite Gucci handbag and maybe a few pearl accessories—you’re ready for the day! (And, if you like this Tuckernuck look, find more workwear/office outfits from them HERE.) 

M.M.LaFleur Black Double-Breasted Dress

All Black Work Outfit

All black outfits are flattering on every body type and can be effortlessly styled. If you struggle with what things “go together,” all black looks are the best. You can learn more about assembling black outfits in my post, “How to Style All Black Outfits.” 

For this all black office look, start with the double-breasted trench coat dress. Everything from the tailoring to the belt to the color to the length create a sophisticated, corporate look that’s still sexy and chic. Pair it with your favorite black heels and sunglasses, and polish it off with gold and crystal stud earrings. Simple and stylish! 

Best Office Dress

Tunic Dress and Blazer for the Office

This look can go from work to weekend in an instant! Start with this colorblock tunic dress and nude heels. As is, the look is definitely preppy, but it isn’t professional enough for the workplace. To get it there, add a blazer, pearl earrings, and a Citizen watch. For shoes, you could wear heels or even white sneakers. (Here’s more on how to wear a dress with sneakers.) 

When you leave work on Friday, remove the jacket, and grab your favorite raffia handbag for a weekend look fit for any occasion, whether it be a date night or wine in the park with your girlfriends. This is the best of the best for transitional style!  (For more ways to style this dress read this post).

Print Dress with a Pop of Color for Work

You can wear prints to the office. This black, white, and magenta dahlia dress is gorgeous and definitely functions as a workwear dress. The print has fun color and timeless femininity, but it’s also refined. For the rest of the look, carry your Carlton Bow Bag (great size for work), add a gold bracelet, and rock some pink shoes to bring out those dahlias. If you like a pop of color, this workwear outfit is definitely for you!

Preppy Work Dresses

Gucci Wool Dress Fall Workwear Look

Preppy looks often come with high-end, quality pieces. This outfit is no different! This Gucci wool dress has a lot of texture, structure, color, and bold visual interest. That means, this luxury piece does pretty much all the work for the outfit! All you need to do is echo those gold tones with a few understated jewelry pieces. Then, for shoes opt for black, white, or gold heels. 

Preppy Dress for Work

Striped Shirtdress Summer Workwear Outfit

Stripes are in every preppy girl’s closet. And a striped shirt dress? Preppy girl essential! A striped shirtdress can work for a number of summer occasions, including work. The dress in this look has a belt to cinch in that waist to give the outfit a more sophisticated shape. For accessories, neutral colors are best to elevate the outfit.

Depending on your workplace dress code, you could maybe ditch the heels for my go-to espadrilles brand or white sneakers!

Office Dresses

Belted Sweater Dress Fall Office Look

For a fall preppy workwear look, you can’t go wrong with this emerald sweater dress from Nordstrom. (If you didn’t know already, Nordstrom has some of the best workwear! Check out this post on Nordstrom work outfits for more.) The dress is a perfect piece for that transition between summer and fall where the mornings are crisp and the afternoons are still warm. To assemble a whole look, add neutral and gold accessories of your choice! 

Additionally, I definitely recommend you wear a belt with this one, because it draws attention to the beautiful ribbing on the dress. Oh, and bonus tip: For cool fall mornings, add a trench coat! It’ll fit with the neutral accents and add to the overall look instead of distracting from it. 

Asymmetrical Midi Dress Workwear Look

Playing with traditional corporate shapes is such a fun way to jazz up a workwear look. For this one, grab the tailored crepe asymmetric pleated dress in camel and pair it with heeled boots or nude/black heels. The dress definitely falls in the preppy category with the classic pleated skirt and blazer combo. But, in true Style Charade fashion, the dress turns the traditional look totally on its head to create something fresh! 

Keep all your accessories really minimal, and though it comes in multiple colors, for work I’d stick with neutrals. The shape is wild enough, color on top of that would be a little distracting (dare I say garish?) for the workplace. Those shades are great for a date night or evening out, but not for the office. But, hey, you could always buy more than one! The dress is pretty incredible. 

Best Work Dresses

Tweed Jacquard Blazer and Dress Set for the Office

This look feels like it stepped straight out of Gossip Girl, and I love that! The jacquard dress and blazer set in black and white is polished, feminine, and definitely chic. It’s comfortable and easy to style too! Nude or black shoes, simple gold jewelry, and a black handbag will draw it all together for a perfect preppy workwear dress look. 

Preppy Dresses for Work

Black Dress Simple Workwear Outfit

If you want something preppy but simple, a black long-sleeved, square neck dress like this one is the right pick for you. It’s preppy, effortlessly stunning, and really versatile even beyond workwear looks. Go all black like we did with the trench dress or sprinkle in some nude/natural tones. Either way, it’ll make you feel beautiful and confident! 

And, much like the tunic dress outfit, you could transition this look easily from work to weekend. You may even have an LBD in your closet you never thought about repurposing as a work dress. Try it out and let me know how it goes!

Spruce up your preppy office wardrobe with these gorgeous work dresses!

Friends, I hope these outfits inspired you to assemble your own fresh workwear looks. Let me know in the comments or on Instagram what looks you decided to try out! Moreover, be sure to return to the blog for more style tips and outfit inspiration. Have a great week!

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