Damson Madder Damson Madder Ilona Striped Rugby Jumper

View on Damsonmadder.com

I have so many praises to sing over this jumper. First: You can’t ignore the 100% cotton knit—it’s the level of cozy that has people snuggling into my hugs in the least weird way. If comfort is a non-negotiable, look no further. 

This rugby shirt isn’t as boxy as the average—it’s got that dreamy slouch that sits just right and is balanced by super intentional hems. Button it to the top or keep it open—both options work. (I love how it pairs over a white T-shirt, too, for that extra preppy look.)

Now to the colorways—for some, this combo of burgundy, cherry red, and cobalt may feel bold. I say lean in! Let it shine with your favorite baggy jeans (mine are The Tall Perfect Vintage Wide-Leg from Madewell) and a loafer (shout out to Ann Taylor for these fun Horsebit Woven Loafers). The look gives stylish intellectual without trying too hard. And for the icing on the cake: the ultra chic DM embroidered logo—a subtle detail that goes a long way.

Frankie Shop Royan Striped Polo – Khaki Multi Stripe

View on Thefrankieshop.com

Equal in quality to the last pick but different in vibe, we have the Frankie Shop rugby shirt. This iteration means business—it’s more fitted, structured, and thicker. And, yes, it’s as luxe as it looks. But I’d be remiss not to point out this shirt’s duality of funky and serious—check out the tailored collar in a surprisingly deep brown, sans the more expected and traditional white. Kudos to the brand for styling this shirt in a way that highlights its personality. It looks incredible over a white button-down and tie, paired with brown tights and shorts—truly accomplishing that business-meets-party feel. I took a similar approach, but with these baggy linen Bermuda shorts from Dissh and the perfect chunky black loafers.

Old Navy Oversized Rugby Polo

$35

$18 at Old Navy

If you skimmed over the first two options to my Old Navy pick, you know what you like. Your vibe is one or a mix of the following: athleisure, overstated, fun, vibrant. This shirt delivers all of that—it’s the elevated, mature cousin of your favorite out-of-the-house T-shirt. Super lightweight and airy, not structured or boxy at all. It’s oversized and slouchy—no buttons to be found. You get all of that without sacrificing style—and one better, this top’s bold, feminine colorways make a statement that intrigues when complementing this traditionally masculine silhouette. My favorite way to style this shirt is with a white tennis skirt (mine are out of stock, but I love this option, too) and these funky Adidas Taekwondo Mei Ballet Flats.