Prada Black: Luna Rossa Black and Amber Woody Colognes

In 2000, in Auckland, an Italian boat called Luna Rossa won the Louis Vuitton Cup, the challenger series for the America's Cup. It was the first Prada Challenge, backed by Prada's chief executive Patrizio Bertelli. Then it lost the Cup itself, 5 to 0, to Team New Zealand. Luna Rossa means red moon, and that sailing team is where the fragrance name comes from.

Prada Black, the name most people search for Luna Rossa Black, arrived in 2018 as the seventh version of the fragrance. Daniela Andrier was the perfumer behind the family, and Yves Behar designed the bottles, which is why the black one looks like a piece of gear. Prada lists bergamot and angelica up top, patchouli and coumarin in the middle, and a woody amber base, and describes it as masculine, woody and ambery, made for fall and winter. Fragrantica points out something I like: there is no lavender here, which is a key feature in so many other Luna Rossa editions.

The trick is to read the first grid like a small wardrobe. Luna Rossa Black Eau de Parfum is the dark suit, for cool evenings. Ocean, in both the Eau de Parfum and the Le Parfum, is the one named for water, so I would try it for the day. Carbon comes as an Eau de Toilette and as an Eau de Parfum with licorice and cypress, and the plain Luna Rossa Eau de Toilette is the simplest way to meet the family.

Paradigme sits beside them, as an Eau de Parfum collection and as Paradigme Le Parfum with amber and vanilla, for anyone who wants Prada's warmer side.

Start with the season, not the bottle. Amber and woody fragrances suit cold air, and a test on a cool evening tells you more than a test in a warm shop. Spray once, walk outside, and check after two hours.

Tom Ford has two here. Ebene Fume, with palo santo and ebony wood, is the smoky and dry one, and Oud Minerale, with smoky woods and musk, is the one to sample next to it. Montblanc Explorer Extreme Parfum is the outdoorsy choice in the same territory. Dior Homme Intense is the one to try if you want the same territory from a fashion house.

Burberry Hero Elixir de Parfum and Rabanne Phantom Eau de Parfum Intense are the two I would reach for on a night out, and Valentino Uomo Born in Roma Intense brings vanilla into the amber. Dolce&Gabbana Devotion Pour Homme Parfum is the last of the group, and the one I would sample beside the Prada.

A pairing I like: the Prada on your neck and a plainer, unscented shower gel, so nothing competes with it in the first hour.

What I would skip: a heavy amber fragrance on a hot commute in July. The same bottle will feel very different in a cold coat.

One rule for tonka: it is a note that changes with time, so test it on skin, then walk away from it. It always smells different at four hours than at four minutes.

Rabanne has three of the bottles in this grid, Invictus Victory Elixir, the Invictus Elixir Collection and 1 Million Elixir, and they are the ones I would compare if you want the Elixir strength. Chambre52 Soleil Tonka is the one that puts the note in its name, and Montale Arabians Tonka does the same.

Armani's Acqua di Gio Profondo has mandarin and patchouli, and for anyone who loves the aquatic family, it is the friendliest way in. Jo Malone London Ginger Biscuit Cologne with tonka bean is the gentle, edible one, and Kilian Paris Angels' Share with tonka bean is the one for people who want their fragrance to feel like dessert with a drink.

Patchouli is the bridge back to the Prada. Luna Rossa Black has a fresh patchouli in the heart, so any of these will sit comfortably beside it in a rotation.

What I would skip: wearing a tonka-heavy fragrance to a small, warm room, like an office or a dinner table for six. Sweet fragrances need space.

Try this before an evening out: spray once on the chest and once on the back of the neck, then wait ten minutes before you leave. What you smell walking out the door is what everyone else will smell at the table.

Dior Sauvage Parfum is the strong, familiar one. Gucci Guilty Eau de Toilette Intense Pour Homme and Yves Saint Laurent L'Homme Le Parfum are the two I would wear with a jacket. YSL Y Eau de Parfum Intense is the sleek, modern one, and Versace Eros Flame is the one with heat in the name.

Montblanc Legend Elixir Parfum and Carolina Herrera Bad Boy Cobalt Elixir bring more concentration to their lines. Bleu de Chanel L'Exclusif is the most restrained of the eight, for a man who wants people to lean in.

A pairing I like: Luna Rossa Black on a weeknight and one of these for a weekend, so you always have a fragrance for the room you are walking into.

What I would skip: stacking a fresh sprayed evening scent on top of a cologne you already wore that morning. Shower first, or pick one.

I think Prada Black is the right first bottle if you like amber and woods but not the sweetness of a vanilla gourmand. Prada lists a fresh patchouli in the heart, and the brand calls it right for fall and winter.

So test it beside Ocean and Carbon, then one from each of the amber and tonka lists. Wear it for two full days before you commit, and give it a proper cold morning. Bertelli's boat lost 5 to 0 in the end. You only need to make a choice you like, and that is the easier race.

After Prada Black, I would use this group to check what else holds your interest before you commit. Prada Luna Rossa Carbon and the Prada L'Homme Eau de Toilette keep things in the house. For something warmer, the Rabanne 1 Million Elixir with vanilla and amber and Invictus Victory Elixir cover the evening end, and Dolce & Gabbana The One Pour Homme Eau de Parfum sits close. When you want fresh, the Light Blue Pour Homme, Montblanc Legend Blue and Chanel Allure Homme Sport are the ones I would pick up. Van Cleef & Arpels Precious Oud is the unusual one, and Versace Eros Energy and Gucci Guilty Elixir are the other two I would test. Wear one scent per arm and leave them for an afternoon. If you want to keep browsing, I also put together Tom Ford Noir Extreme and the Spiced Amber Colognes Around It and Stronger With You Absolutely and Other Rum, Vanilla and Tonka Colognes.