Class to Night Out: Shirt Dress

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Shirtdresses on the runway


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Do you struggle with transforming your outfits from day to night? Don’t worry, CF is here to help turn that daily annoyance into a fun challenge. This column will focus on one piece per week, and teach you how to take your look from study sessions in the library to dancing the night away.

Nothing is as effortlessly sophisticated as the shirt dress. It's an undeniable wardrobe classic that can be anything from super polished to a beach cover-up, making it a perfect candidate for a Class to Night Out post! Whether your favorite shirt dress is ultra girly or utilitarian-inspired (or anywhere in between) you can find a million different ways to wear it.

Read on to see the two outfits I've created, featuring a very feminine, '50s-esque shirt dress that I think Zooey Deschanel would go nuts over.

Shirt Dress: Class

how to wear a pink shirt dress for day with printed gray tights brown flat ankle boots printed nautical tote and silver anchor earrings


Dress, Tights, Bag, Boots, Earrings

For a cute indie look, pair the dress with some gray printed tights - try a pair with subtle dots like these, or go crazy with a heavy floral or cheetah print! The collar on this dress reminds me of those sailor dresses our moms were so insistent on putting us in back in the day, so why not embrace the throwback with silver anchor stud earrings and a navy anchor-print tote bag? Complete the look with a pair of sturdy-but-cute flat ankle boots.

Shirt Dress: Night Out

how to wear a pink shirt dress for night with black oxford heels cameo earrings colorblock pastel clutch pearl necklace and oversized cocktail ring


Dress, Clutch, Heels, Necklace, Earrings, Ring

Since this dress is a little bit childhood-chic, it's important to accessorize correctly in order to create a more sophisticated look for night. Add elegant jewelry like a layered pearl necklace, cameo earrings or an oversized cocktail ring (or all three!). Next, create a bit of an old school glamor aesthetic by wearing black oxford pumps. Finally, add a modern pastel colorblock clutch to complete the look.

Your thoughts?

Do you have a shirt dress? How do you style it? Be sure to let me know what you think of the outfits in the comments, I'd love to hear your thoughts!