Now Reading
Deal or Disaster: How To Look Preppy, Not Preposterous


Deal or Disaster: How To Look Preppy, Not Preposterous

2020 was a year of mostly sweatpants for many people so the idea of looking preppy may feel bold and new. But if you’re not careful, you might end up looking preposterous!  HBO is rebooting “Gossip Girl” so Upper East Side prep school looks might be making a comeback. 

Today, we will look into preppy dresses to dress up our dull days. Let’s find the best deals!

This soft fluid dress with a pleated skirt from REDValentino is truly elegant. REDValentino is Valentino’s line for young, urban customers, aka gossip girls. RED stands for Romantic Eccentric Dress and combines sophistication with city street style fashion. You could dress it up by wearing it with white socks and black loafers, or dress it down and wear it with comfy sneakers for that city rush hour.

Photo by REDValentino

This little black dress is absolutely chic. It has a contrasting white crepe collar and a thin scarf tucked under it, which ties into a beautiful bow.

Or, you can get a black crepe satin necktie dress from REDValentino as well. It looks very similar to the one above, but it’s almost three times cheaper! I know, you’re welcome!

Photo by REDValentino

Ted Baker offers the ZAZU dress in a similar style, for a similar price. It’s a mini pleated dress that looks classy and teasing at the same time. For a classy look, wear it with black tights and black heeled pumps. If you want to appear more approachable and down-to-earth, style this dress with a pair of cowgirl boots. Yeeha to the next dress! 

Photo by Ted Baker

If you are looking for something close-fitting and comfortable that is still somehow both bold and classy, Tory Burch created a Scarf Sweater Dress just for you. It’s 100% wool, which speaks for its quality. It also has a perfect length, just above the knee, and would be great for travel or a commute because you won’t need to be constantly pulling down on a skirt that, truth be told, is maybe a little too short. The sleeve length is optimal, too, if you don’t want to show too much arm. It has navy and white knit sashes attached from the collar, which you can wear like a tie or knot into a feminine bow, depending on the look you’re going for. So, bow down only to your needs!

Photo by Tory Burch

If black and white preppy dresses feel a little too conservative or slightly boring for you and your style, would advise adding some pink! (Surprise, surprise.) Or, simply go Gucci. Their pre-fall 2018 collection had a preppy dress with an ivory silk top and a black devoré-velvet skirt but you can still find it on some fashion e-commerce sites. What makes this dress stand out is a pink grosgrain brooch decorated with crystals. If you were to buy a Gucci bow brooch as a separate accessory, you would need to part with about $400…

See Also

Photo by NET‑A‑PORTER 

If you want a dress that looks polished but is also very snugly, you could go for a polo collar long sweater dress by Lacoste. Longer dresses, even though it might seem counterintuitive, give you more comfort and freedom. Also, it’s 50% off right now. 

Photo by Lacoste

And just when you thought that all preppy dresses look pretty, it’s time to show you how it can go wrong. Things can go from preppy to preposterous pretty fast! 

This black satin ruffled babydoll dress by Gucci doesn’t belong in the world of “Gossip Girl” but might make people gossip about you (like, in a bad way though).  

Photo by SSENSE

This Yoke Plaid Dress from SHEIN would work really well on social media… if they had Instagram or TikTok in the 1800s.     

Photo by Shein

© 2024 All Rights Reserved.

Scroll To Top