How to Wear a Polo Shirt Without Looking Like a Middle Manager

The polo is a style staple and one of the most versatile shirts a man can own. Donning one is an easy way to level up your look when the occasion calls for something a notch above a t-shirt.

But that ease can lead to complacency, and the polo often ends up in some very unstylish territory.

A guy needs a collared shirt for an event, grabs one off the rack at Kohl’s, throws it on thoughtlessly — and ends up looking like a middle manager at Acme Co.

Maybe that’s okay if you’re about to give a PowerPoint presentation on Q3 sales, but a lot of guys would like to look sharper in a polo for social occasions, and even at work.

If you want yours to read as more stylish and handsome than boring and corporate, follow these five guidelines:

1. Dial in the Fit

Middle Manager Move: Oversized polos with sleeves hanging past the elbow and bodies billowing like sails.

Manly Upgrade: As with any garment, fit is king — and that’s especially true with the polo, where a loose, shapeless cut only adds to the shirt’s reputation as an afterthought. Instead of swimming in a sloppy shirt that hides your build, opt for a polo that flatters your frame with:

• A slim-but-not-tight silhouette.
• Sleeves that hit mid-bicep and hug the arm a little.
• Length that lands mid-fly — long enough to tuck, short enough to leave out.

2. Choose Classic Fabrics

Middle Manager Move: Shiny, synthetic polos with moisture-wicking sheen.

Manly Upgrade: Tech fabric exudes an air of the office and suburban-dad-dom. So save the shiny polos for the golf course, and choose polos made with traditional pique cotton or jersey knit. Jersey and pique cotton offer structure without stiffness and a texture that looks classic and inviting.

3. Dress It With Intention

Middle Manager Move: Wearing a polo as part of a generic business-casual getup — tucked into pleated khakis, paired with a braided belt and boxy dress shoes.

Manly Upgrade: You want to treat the polo like a grown-up essential, not a placeholder. Give some thought to how you wear it and what you wear it with by:

• Pairing it with tailored chinos, trousers, or well-fitting jeans.
• Adding refined-yet-relaxed footwear: loafers, chukka boots, clean sneakers.
• Accessorizing with a cool bracelet or watch (or both, like Clark Gable above)
• Tucking it in (if you want) but anchored with a leather or canvas belt.

4. Branch Out With Colors

Middle Manager Move: Wearing only safe colors — navy, black, or corporate baby blue.

Manly Upgrade: There’s nothing wrong with a polo in a basic color like blue, but when you’re trying to look more stylish and sharp than stiff and stale, branch into earth tones (olive, rust, cream), deep classics (burgundy, forest green), or even a light mint or pink for spring and summer.

5. Level Up With Layers

Middle Manager Move: Nothing but the polo up top.

Manly Upgrade: One-dimensional outfits are fine, and a necessity for the hottest months of the year. But when the weather allows, adding a layer adds visual interest to your getup. Polos can look great with a lightweight jacket, cardigan, or even a sport coat over them.

Don’t Let the Polo Phone It In

The polo shirt’s got plenty more potential than being the go-to uniform of the apathetic office worker or the off-duty regional manager. With better styling, it can look intentional and sharp — put-together but still laid-back. Wear it with some purpose, and it rises above the cubicle to become a sartorial statement.

This article was originally published on The Art of Manliness.