What to wear from the office party to Christmas dinner

Take your trousers to the tailor the first week of December. Not the 18th. Every alteration shop in America gets buried the second week of the month, and the difference between a hem that's right and a hem that's stacked on your shoe is about eleven days of lead time you either gave them or didn't.

That's the whole secret to holiday dressing, honestly. It isn't buying anything. It's handling the small stuff early, so on the night you can get dressed in nine minutes and then forget what you're wearing.

You've got three rooms to get through. The office party, somebody's house, and the family table. One jacket covers all three if it fits at the shoulder.

Start at the shoulder seam, because nothing fixes that one

Stand in front of a mirror with the jacket buttoned. The seam where the sleeve meets the body should sit right where your shoulder stops and your arm starts. If it hangs out past that into a little divot, the jacket's too big and no tailor is going to save it cheaply. If it's biting into the top of your arm, it's too small and you'll know by the second hour.

Everything else is fixable. Sleeves should end so about a quarter inch of shirt cuff shows. Waist can be taken in. Length should cover your seat with a little to spare.

Buttoning: top button only on a two-button jacket, and you should be able to get a flat hand between the button and your chest, not a fist. Unbutton when you sit. Always. A buttoned jacket in a dining chair pulls into an X across your stomach and that's the picture that ends up on the fridge until 2041.

The office party is one notch up from Tuesday, not four

The guys who get this wrong go in two directions. One shows up in exactly what he wore to the 10 a.m. standup and looks like he forgot. The other shows up in a three-piece with a novelty tie and looks like he's hosting.

Go one notch. If you normally wear a polo and chinos, that's a button-down oxford, wool trousers and a sport coat. If you normally wear a suit, keep the suit and swap in a knit tie or a flannel trouser to soften it.

When the invitation says festive attire, it means dark, with one interesting thing. That's it. Nobody's asking for a red velvet dinner jacket. A dark green knit tie, a deep burgundy sweater under the jacket, a plaid trouser if you own one already. One. Two "interesting things" and you're a theme.

Skip the light gray suit in December. It reads like April. Charcoal, navy, brown, dark green, oxblood. The season is dark and so is the fabric.

Wool flannel, corduroy, and the velvet question

Fabric does more work in winter than cut does. A worsted wool trouser looks thin and office-y at night. The same trouser in flannel looks warm and expensive under a string of patio lights, and it costs about the same.

Corduroy: yes, in a fine wale, in a jacket or trousers but not both. Moleskin trousers are underrated and hide a lot.

Velvet, since somebody's going to ask. A velvet blazer looks genuinely great if it fits at the shoulder and you don't apologize for it all night. The trade-off is real though. It grabs every hair from every dog in the house, it water-spots in a drizzle, and it needs a lint brush in your coat pocket. If you own one, wear it. If you're buying one for a single party, buy the flannel trousers instead and get twenty more wears.

Shoes, salt, and the parking lot

Leather soles on an icy lot are a comedy routine. Wear a rubber-soled derby or loafer, or carry your good shoes in a bag and change in the car like every man who's ever lived in a winter city.

Salt stains show up as a white tidemark the next morning. Mix white vinegar and water about one to two, dab it with a cloth, let the shoe dry away from the heat vent, then condition. Don't skip the conditioning step. Salt dries leather out and cracked toe boxes never come back.

Over-the-calf wool socks. Nobody needs to see your shin when you cross your legs, and December isn't the month for the bare ankle look.

For the women: pass the folding chair test

Sit down in the fitting room. Then stand up. Then reach up like you're getting a platter off the top shelf. If any of those three moves makes you adjust something, you will spend the entire night adjusting it and you'll remember the dress instead of the night.

The garments that genuinely earn their place in December: a crepe or ponte sheath that doesn't wrinkle when you drive forty minutes to your in-laws, a fine merino knit midi, and wide-leg wool trousers with a silk or satin blouse. That last one is the most forgiving thing going and reads more polished than most dresses.

Three-quarter sleeves are the workhorse. You can carry a casserole, hold a baby, and not push anything up to your elbow every ten minutes.

Block heel over stiletto on any night that involves a driveway. And if you're the one cooking, pick something you can put an apron over without crushing it. Nothing with a bow at the waist.

The knit swap gets you from party to family table

Same jacket, same trousers. Pull the dress shirt and tie, put on a fine-gauge merino crewneck underneath. Now you're dressed for your mother's dining room instead of the conference center, and it took four minutes.

At the table, the jacket comes off if you're carving or hauling plates. Roll your sleeves twice, cleanly, not the crumpled push-up. A man in a good sweater and wool trousers carrying a turkey looks like the host. That's the whole goal.

The fixes you'll actually need that night

Wrinkles. Hang the jacket and shirt in the bathroom while you shower and give it ten minutes of steam. A handheld steamer does it better and faster. Never put a hot iron directly on a wool jacket. You'll flatten the nap and it shines forever.

Gravy. Blot, never rub. A drop of dish soap worked in with your finger, then cold water. Grease needs the soap, so plain water alone will set it.

Cranberry or red wine. Cold water immediately, as much as you can get through it. Hot water cooks the sugar into the fiber.

Whatever you couldn't get out. Don't put that shirt in the dryer. Heat sets the stain permanently and the shirt's gone.

Get the haircut two weeks before the first party, not two days. Two days out, it looks like a haircut. Two weeks out, it looks like your hair.

Then stop thinking about it. The best-dressed guy at any party is the one who never once checks his reflection in the microwave door.