Preppy Polos: 12 Ways to Wear Your Favorite Collared Shirts

by Emily Tozer

Preppy Polos: 12 Ways to Wear Your Favorite Collared Shirts

The fashion set has an unexpected go-to top this season: the polo shirt. Pull out your collared shirts to recreate one of these street style looks for work or the weekend. You might find it’s as easy as swapping out your tired V-neck for this preppy wardrobe staple!


With Flared Jeans



Take advantage of the season’s biggest trend, and tuck a crisp polo shirt into a pair of flared jeans as Sydne Style did here. The ’70s staple helps tone down the preppy feel of collared shirts. Finish the look with chunky sandals.


With a Mini Skirt



To make your collared shirts look cool, pair them with an unexpected statement piece like Pandora Sykes‘ leopard mini skirt. Finish the look with sandals by day or pointed pumps by night.


With a Sweater



Collared shirts are perfect for layering once the weather starts to cool. Take a short- or long-sleeved polo shirt into fall by wearing it under a lightweight sweater. This outfit on Lady Addict is a flawlessly chic look for the office.


With Leather



Toughen up a preppy polo shirt by teaming it with a leather skirt or shorts and ankle boots. Take a tip from this fashionista on Style du Monde, and stick to a monochrome color palette for the most modern take.


With Boyfriend Jeans



Ease into the trend by pairing a polo shirt with basics, as Raspberry & Rouge did. Worn with boyfriend jeans, it’s just as easy as a crew-neck tee but with significantly more style points. We love the sporty zip on this one in place of buttons.


With Wide-Leg Pants



Wide-leg pants are big this season—no pun intended—so this is the perfect opportunity to knock out two trends in one outfit. Think a polo and khaki sounds too uniform? Leandra of Man Repeller proves that with a few simple tricks—rolled cuffs and a half-tuck—it works!


With Printed Pants



Hallie Daily has your next casual Friday outfit sorted! The two most important things to look for when you’re picking a polo shirt are the fit and the fabric. A slimmer fit and lightweight jersey fabric tone down the prep factor, so it’s significantly more versatile. Half-tuck it into a pair of tailored printed pants.


With a Midi Skirt



Give your collared shirt a feminine twist as Suburban Faux-Pas did. Tuck it into a full midi skirt—the silhouette flatters everyone—and slip on pointed pumps for a daytime event or a fun brunch.


With Mixed Prints



We haven’t stopped mixing prints! Samio gives this look a refresh with a cute polka-dot print polo shirt and skater skirt. As we’ve said before, sticking to a cohesive color palette is the key to making this work. Complete the look with a pop of red lipstick!


With a Denim Skirt



This season, every gal needs a denim skirt, whether it’s pencil, pleated, or A-line. Not only is it a building block for many ’70s-inspired looks, but it’s also as easy to wear as, well, jeans. Sydne Style in a polo shirt and denim skirt is the perfect example.


With Boyfriend Shorts



Pair a collared shirt with boyfriend shorts and flats or sneakers, as Sarah of Classy Girls Wear Pearls did. Boyfriend shorts have the same relaxed effect as their jean counterparts. Make sure the fit is just right; they should be loose in the leg, and a few rips never hurt.


With Ripped Jeans



Hallie Daily makes her polo shirt look casual and elegant, and her outfit is super-easy to recreate! We think it works best with a crisp white collared shirt. Just add ripped jeans, pointed pumps, and a statement coat for a chic weekend outfit.