The rugby shirt is one of the rare clothing pieces that crosses style boundaries with ease. On one side, it’s a preppy icon tied to Ivy League campuses and clean-cut looks. On the other, it’s a streetwear staple, oversized and styled with sneakers and cargos. So which side fits you best — or can you rock both?

The Preppy Rugby Shirt Look

Rugby shirts have been a cornerstone of preppy fashion for decades. With their bold stripes, crisp collars, and tailored fit, they give off polished-yet-casual vibes.

How to style it preppy:

• Pair with chinos or slim trousers

• Add loafers, boat shoes, or minimalist sneakers

• Layer under a blazer, sweater vest, or quilted vest

• Stick with classic color palettes like navy & white or burgundy & cream

Where it works:

• Class, study sessions, casual Fridays

• Smart-casual dinners or outings

The Streetwear Rugby Shirt Look

Streetwear takes the rugby shirt in the opposite direction. The fit is looser, the colors are bolder, and layering is the name of the game. Inspired by hip hop, skate culture, and Y2K vibes, this version turns a classic into a statement piece. For some seasonal inspo check out our rugby shirt fall outfits.

How to style it streetwear:

• Oversized fit, worn loose over cargos or baggy denim

• Layered with hoodies or long-sleeve tees

• Finished with chunky sneakers or boots

• Bold color combos like navy & pink or black & gold

Where it works:

• Streetwear daily fits

• Skatepark sessions

• Casual weekend hangs

Can You Do Both?

The beauty of rugby shirts is that they’re versatile enough to fit both lanes. Rock a slim-fit navy and white rugby for a clean preppy outfit one day, then throw on an oversized pink-and-navy version with cargos the next. It all comes down to fit, color, and accessories.

The Takeaway

Whether you vibe with the preppy aesthetic or lean into streetwear culture, rugby shirts give you the flexibility to make it your own. They’re not stuck in one box and that’s why they’ve stood the test of time.

Shop the Look: Rugby Shirts