Kate Moss wore Hunter Original Talls to Glastonbury in 2005, and that is the moment the wellie stopped being a farm boot and became a fashion one. Every rainy week since, I have thought the same thing: if you are going to wear rubber, wear a color.

Hunter is older than people expect. It began in 1856 as the North British Rubber Company, started in Scotland by an American, Henry Lee Norris, who came over to work Charles Goodyear's rubber patent. The Original Tall dates to 1956, is handcrafted from 28 parts, and still carries the little moustache on the toe and the buckle at the side. That is the whole appeal of red Hunter boots: a very old shape in a color that makes a gray Tuesday look planned.

Start with the Original Tall Gloss in Military Red if you want the one everybody recognizes, shiny and knee high. The Original Back Adjustable in matte red has a gusset up the back, so it is the one for wider calves. The Original Short Gloss is my weekday pick under a cropped trouser, and the Original Chelsea Gloss in Military Red slips on under a straight jean with no buckle to fuss with. The Tour Short folds flat for a suitcase, which is rare in rubber.

For the playful end, the Play Short sits on a chunky platform, the Liberty has a deeper tread, and the Play Short Star Cloud adds a glitter fleck. Try them with a sock that shows at the top. Wear one red boot against navy or camel and let everything else stay quiet.

The word Wellington comes from the Duke of Wellington, who had his shoemaker rework the Hessian boot, so every red rain boot below descends from one duke's request. Plenty of brands make a good one now.

The Barbour Wilton Chelsea is matte red rubber with navy gores and a lug sole, a good pull-on for a city commute. The Ariat Kelmarsh Shortie has a navy collar and striped pull loops, which reads a little equestrian. The Bogs Amanda II Mid is a textured red mid-calf boot with a pull tab and a fabric lining, and the Melissa Ultra Boot is glossy red PVC on a thick platform with oval cutouts, the most toy-like of the lot. Ilse Jacobsen makes two lace-up versions in natural rubber, the short Rub boot with a crepe sole and the tall one with black laces. The Comfortview Uma is a vivid red chelsea with a low heel, and the Sorel Out N About IV Chelsea is a deep, high-gloss red with a black gore panel.

Pair the shorter ones with a black midi skirt and thick tights. Try them with the trousers you actually plan to wear: rubber that bunches at the ankle will bother you by lunchtime.

Rubber can bloom a white, powdery film over time. It is a normal trait of natural rubber, so buff it off with a soft cloth and keep the boots away from direct heat.

What I would skip: the Melissa on a day with real puddles, since the platform is more about looks than traction.

A red boot in leather behaves like a good lipstick: one is enough, and everything else steps back. These are for dry streets and drizzle, not downpours, so treat them as shoes first.

The Fly London Soil Wedge Chelsea is bright red leather with a cream gore on a chunky black wedge, and it is the loudest here. The Camper Pix London Chelsea is a deeper red with black elastic and a ridged lug sole, borderline between red and oxblood, so check it in daylight. The Mutma Samuda in red embossed leather has a tooled texture and a heavy black lug. For something sleeker, the Steve Madden Khelan is a glossy sock-style ankle boot with a square toe and a two-inch sculpted heel. The Miz Mooz Flicka has red laces on a stacked heel, while the Juke has black laces and a block heel. The Fly London Bink is red suede on a platform wedge, and the Journee Cappri is a crimson glossy bootie with a side zip.

Wear them with black denim or a camel coat and let the boot be the only red. Walk a full lap in the fitting room: wedge and lug soles feel heavy on the first step, and you want to know that before the commute. Press the leather at the ankle and see whether it creases cleanly.

What I would skip: suede on a day that might rain, since suede and rain do not get along.

Lady Diana Spencer was photographed in Original Talls in her engagement photos in 1981, so a red Hunter in the cold has royal precedent. This row is the winter side of the story.

The Hunter Original Tall Insulated in Medium Red is matte rubber with a warm lining and the familiar buckle. The Hunter Maribels is a glossy red quilted puffer with a drawcord collar on a lug sole, and Hunter calls it a winter boot, not a rain boot, so treat it accordingly. The Moon Boot Icon Nylon is padded red nylon with the white logo band and drawcord laces. Sorel has two: the Whitney III is a quilted bright red bootie with cord lacing and a cream platform, and the Out N About IV Mini Puffy is a pull-on version with the same cream sole. The Inuikii Mountain High is a tall red puffer with cream criss-cross laces and a drawstring top. For something less padded, the Taos Mini Crave is red leather with a buckle and cap toe, and the Miz Mooz Preslee is antiqued red leather with a side zip.

Wear the puffers with a long down coat in black or cream, and the leather lace-ups with wool trousers. Check the sole in the shop: a deep lug grips ice, and a flat platform does not. Tug the drawcord and zip once to see they run smoothly.

What I would skip: the Moon Boot on soaked pavement, because padded nylon is made for snow, not standing water.

Red western boots are the loudest thing you can put on a hemline, so decide first whether you want the boots or the outfit to do the talking. I usually pick the boots.

The Jeffrey Campbell Finn is tall tooled leather in a bright cherry with a pointed toe. The Ariat Beaux J-Toe is a mid-calf crimson boot with a white ribbon bow inlaid on the shaft. Dingo has three here: the Evita is bright red suede with tonal embroidery and cutouts, a sixteen-inch shaft and a three-inch heel; the High Cotton is leather with contrast stitching and a snip toe; and the Walk West is red suede with long fringe down the side. The Corral L6117 has cream inlay stitching on a fourteen-inch shaft. Away from the ranch, the Bronx Liliana is a knee-high fold-over leather boot on a slim kitten heel, and the Steve Madden Provoque is an over-the-knee in red with cascading fringe and a stiletto.

Wear a western boot over straight dark jeans, or under a slip dress with a leather jacket. Bend your knee in the fitting room and watch the shaft: it should clear the back of the knee without pinching. Ask yourself whether you can pull them on alone, because a stiff pull tab matters.

What I would skip: fringe boots with a fringed jacket, since the two will fight each other.

Decide where you live first. If it rains more than it snows, buy a Hunter in rubber, and Military Red if you want the shine. If you have to walk through the cold, the insulated tall or the puffer is the one.

After that, add one leather chelsea or western boot for dry days, and wear it with black. That is a whole red wardrobe with four pairs at most.

Kate Moss wore the boot to Glastonbury in 2005 and made it look easy. A red pair still does that for me on a wet morning.

For the rest of the lineup, I rounded up Hunter boots for women in tall, short, Chelsea and puffer styles.