The Collar and the Buttons

Both buttons undone lets the collar fall open at the neck, the way the shirt looked on a tennis court. Use that in warm weather and anywhere with no stated dress code. One button pulls the opening in to about two inches. Offices and clubhouses expect that setting.

Fastened to the top the collar stands around the throat. This one splits opinion. Under a jacket it closes the neck where the lapels cross, though most menswear writing still argues for leaving one open, on the grounds that a closed neck shortens it. Try both in a mirror before the room sees either.

Keep the collar itself down indoors. Put it up for sun on a boat or a court, where it covers the back of your neck. Anywhere else a raised collar dates the outfit to about 1985.

Before you try, check whether yours will even hold: fold it back, let go, and count to ten. Stiff ribbing is still up.

The Hem Decides the Tuck

Start here, before the closet. A short hem takes tucking off the table, and an untucked shirt then covers the waistband you were going to put a belt through. Pick the shirt up and look at the shape of the bottom edge.

A curved hem cut to the hip gives you both options. Look for that when you next buy. Short straight hems were built to hang outside. A tuck leaves you two or three inches of shirt to push into the waistband, and it comes back out through the day.

Tuck it for an office, leave it out everywhere else, and check where an untucked hem lands. An untucked hem sits one to two inches below the waistband: over the belt, short of the back pockets.

Half tucking at the front puts the buckle on view while the back hangs at its full length. Use it on a shirt cut long, in a setting where a full tuck would be more formal than the room. Wear a belt worth showing or skip one entirely.

You can read the hem off the shirt itself. Run your hand along the bottom edge: a dip at the side seams means it was built to tuck. Then put it on and see where the hem lands on you. A hem cut for six foot two sits at the hip on that frame. Two or three inches up, on a shorter one, it sits at the waist. There is nothing below the belt line to tuck.

If you own one polo, make it the curved hip-length version. A shorter hem rules out tucking on every outfit below.

Picking the Pants

Your waistband goes on display the moment you tuck, so the pants underneath have to be worth looking at. Flat-front chinos in stone, olive or gray take a polo in any color, as does dark denim wherever the office allows it. With a full tuck, wear a belt, since empty loops above a tucked hem are the part of an outfit people notice first.

Leave the shirt out and the covered waistband takes the pressure off the pants. Wide-leg cuts and plain shorts both work under an untucked hem. An untucked hem cuts across you at the hip, so the pants below it can be as plain as you like.

Over shorts, keep the hem above the knee and the polo out. The untucked hem then sits several inches below the waistband.

Shoes, Belt, Watch

Leather loafers, suede derbies, a clean white leather sneaker: tucked, the shoes go up a level with the shirt. Leather and canvas both sit better with a tucked shirt than a running shoe does, though trail shoes with tailored pants has been a standing combination for a few years now, so take this as the conservative call. Untucked, canvas and sandals come back in.

Match the belt leather to the shoes, on a small flat buckle. Plenty of otherwise careful outfits fall down on a black belt under brown shoes.

Polo collars sit flat, with no stand for a knot to rest against, so I would leave the tie for a different shirt.

Sleeves

Roll a polo sleeve and the fold lands at the widest part of your arm, then works itself loose over the next hour. The sleeve holds its shape where the maker set it, at the middle of the bicep.

On a long-sleeve polo, push the sleeves up to the forearm. The cuff rib grips there and stays put. Most people try to roll them first and spend the evening pushing them back up.

On a trim polo the shoulder seam lands at the edge of your shoulder, with the sleeve ending around the middle of your bicep. Sleeves reaching your elbow mean the shirt runs a size large. Check the collar before you decide. On a shirt bought a size up the collar scales up with it and sits loose around the neck, so take that one down a size. A cut designed oversized keeps the collar at normal size under the dropped shoulder.

What Goes Underneath

Nothing, on a piqué polo in a mid or dark color. Wear an undershirt only under a white polo in a light knit, and make it a V-neck close to your own skin tone, since a white one shows through at the shoulders. Open-knit and mesh show skin through the stitch, so put a plain tank in a matching tone under them.

Color and Pattern

Rank how loud the shirt is before you pick the bottom half. A single color takes a pattern below it. Stripes and contrast collars give the shirt its own rhythm for the bottom half to leave alone. A graphic, a crest or a camo body needs plain pants, plain shoes and no second logo anywhere on you.

Past navy, white and black, color is mostly preference. For sweat, a mid-tone in olive, dusty blue or clay does better than either extreme, though it is worth testing on one hot day before you buy three.

Layering a Polo

A polo under a jacket puts two collars at the same neckline, one folded and one flat. The outer piece decides how that reads.

Reach for a knit vest before anything else. A vest neckline stops at the shoulder seam, so your collar sits out on top of it with nothing crossing it.

Leave the polo collar outside the lapel of an unstructured jacket or an overshirt. A crew-neck sweater over the top also works, collar out, placket hidden. Hoods sit better over a flat neckline than over a folded collar.

Oversized Cuts

The dropped shoulder and the wide body are the point of the cut, so stop measuring them against a trim polo and start dressing around the volume.

The hem still has to clear the waistband, whatever the cut.

Give the bottom half more room as the shirt gets wider. Slim pants under a boxy polo leave you top-heavy until you widen them to match.

Layering is where an oversized cut earns back the width. Put a vest or an unstructured jacket over the top and the shoulders come back in while the body keeps its volume.

Fixing a Bad Fit

A polo can be off in the length, the chest or the width, and each of those has a way around it that does not involve buying another shirt.

Too long: tuck it. Tucking a long hem puts the extra fabric to work, since it is that length below the waistband that holds a tuck through the day.

Too short: wear it out as a cropped cut, over a high waistband that keeps the two edges overlapping all day.

Too tight through the chest: two buttons open lets the placket lie flat. A vest or an overshirt over the top covers the rest of the pull once the weather turns.

Too boxy: leave it out over wide-leg pants, where the width has the length below the waist to hang into.

Summer and Cold Weather

On the hottest days a polo walks through doors that ask for a collar, and it breathes about as well as the T-shirt you would otherwise reach for. That is most of the argument for owning several. That gap is why a summer rack runs on polos, with the tees kept for days off. Reach for piqué over flat jersey and a mid-tone over either white or black, with two buttons open, the hem out and shorts below. Whether you go sockless with the shoes is your call.

In cold weather the polo turns into a base layer that still shows a collar at the neck of whatever goes over it. A long-sleeve version slides under a jacket without leaving bare forearm between the two.

Outfits, Head to Toe

Ivy League. Navy piqué, one button open, tucked. Stone chinos with a flat front, sitting at the natural waist. A brown leather belt, and brown penny loafers in the same leather. Socks in a color close to the chinos, or none showing at all. A cotton sweater over the shoulders with the sleeves knotted at the chest, the detail this whole look is known for. A steel watch, and sunglasses with a thin frame.

Country club. White or pastel piqué, one button, tucked into khakis. A woven or braided belt in tan leather. Loafers or plain white leather shoes. A cap, and sunglasses kept on the face. With everything below the shirt kept neutral, this is the look with the most room for color in the polo itself.

Riviera. A long-sleeve piqué in white, both buttons open, tucked into high-waist pleated pants in beige or cream. The pleats give them movement through the hip. The leg drops in a soft line over the loafer. Tan leather loafers, no socks. A slim belt matching the loafer leather exactly. Push the long sleeves to the forearm and leave them there.

Terrace. A polo with twin tipping at the collar and cuff, both buttons open, worn out. Slim indigo jeans, or the flat-front sta-prest pants the look was built on, hems rolled once at the ankle. Desert boots, loafers or low sneakers, all three of which the mod version of this look has used since the sixties. A harrington over the top with the collar sitting outside it. Everything below the waist stays plain so the tipping at the collar can do the work.

Oversized street. The widest polo you own, worn out, both buttons open or a half zip left down. Wide-leg pants or pleated shorts, cut long enough that the hem of the shirt and the rise of the pants overlap by several inches. Canvas sneakers with some bulk to them. No belt. A graphic, a crest or a camo body belongs here. Keep the pants and the shoes plain under it, in black, stone or a washed indigo.

Read the five in order and the collar stays down through every one. Buttons open and hems come out as the settings get warmer. The pants are widest at the Riviera and street ends and narrowest in the middle. Shoe leather stops having to match a belt once there is no belt on show.

Which Look for Which Place

Those five cover most places you would wear a polo, with small changes.

An office or an interview. The Ivy League setup without the sweater, in navy or charcoal, nothing on the chest. Add an unstructured sport coat for a more formal room.

A golf course or a club. Country club, and check the code before you go. Most put it in writing: a collared shirt, worn tucked in, on a hem long enough to stay in through a swing. Newer courses have started dropping the rule.

A flight or a long drive. Oversized street, over pants with an elastic or drawstring waist. A knitted collar comes out of a long sit with its shape intact.

A hot Saturday. Oversized street again, over shorts.

Two settings sit outside the five.

Dinner or a date. A solid mid-tone left out over dark straight-leg denim, two buttons open, dark leather shoes. Black and deep tones hold up better under low restaurant lighting. They also hide whatever you spill.

An outdoor wedding with no stated code. A long-sleeve polo tucked into wool or linen pants, leather belt, loafers. The sleeve carries some of the formality a jacket would otherwise supply, so you can stand in the sun all afternoon without one.