Comfort after sixty that still looks like you chose it

Most closets after sixty aren't full of bad clothes. They're full of clothes bought for a body you had in 1998, worn by a person who never re-measured and never will, because the number on the tag is part of how he thinks about himself.

Start there. Get a soft tape measure, stand in front of a mirror, and write down five numbers: neck, chest at the fullest point, natural waist, sleeve from center back to wrist bone, inseam. Do it in the morning. Then compare those to what you've been buying.

The neck is where it usually goes wrong for men. Necks get thinner with age even when waists don't, and a collar bought at 16½ when you're now a 16 sits away from your throat like a napkin ring. You notice it in every photo and you blame your posture. It's the collar. A half inch of gap makes a $200 shirt look borrowed.

For women, the same principle lands on the band size. Band and cup both shift after sixty, and until that measurement is right, nothing layered over it hangs the way the pattern intended. Get measured properly at a shop that does it for free. Everything above the waist improves the same afternoon.

Most of you also got shorter, and your pants didn't

Spinal discs compress. Nearly everybody loses some height between fifty and seventy-five, and the clothes don't shrink to match. That's why trousers that once hit clean at the shoe now pool over the laces in two soft folds and read as "borrowed from a taller man."

This is the cheapest upgrade available to you. Take four pairs of pants to a tailor and ask for a half-inch to an inch off the hem, with one break at the front and the back hem a quarter inch lower. Ask for the original hem width to be kept if they're jeans, so the leg opening still looks right.

While the pants are there, hand over your two best shirts and ask for the body to be taken in at the side seams and the sleeve shortened so a quarter inch of cuff shows past the jacket. That's a handful of alterations and a modest bill, and it'll do more than anything new you buy this season.

The waistband question, settled

Elastic isn't the enemy. Visible elastic is.

The line is simple: if somebody can tell how your pants stay up, they're loungewear. If they can't, they're trousers. What you want is either side-tab trousers, which adjust with two small buckles at the hips and don't need a belt at all, or a flat-front pant with a hidden stretch waistband sewn into the inside of the band. Both give you two or three inches of give after a big dinner. Neither announces itself.

What to leave on the rack: the drawstring that hangs out the front, the elastic gathered all the way around so the fabric puckers like a curtain, and the pull-on pant with no fly. Those three details are the entire difference between comfortable and given up.

For women, ponte knit trousers do the same job. They stretch, they hold a press, they don't bag at the knee by 3 p.m. Buy them in navy or charcoal before you buy them in black, because black bottoms only look sharp next to other black, and they show every speck of lint at the mailbox.

A soft jacket is doing what your sport coat used to

The structured blazer with the padded shoulder and full canvas is a beautiful thing and it's also a small piece of armor. Shoulders round forward a little with the years, and that stiff shoulder line stops sitting on you and starts sitting near you.

Switch to unstructured. An unlined or half-lined jacket in a knit or a soft wool hopgene weave has no shoulder pad, no chest canvas and about a third of the weight. It moves when you reach for the top shelf. You can drive in it. It packs into a carry-on and shakes out fine.

It still has lapels, a collar stand and real buttonholes, which is the whole point. You get the outline of a jacket with the feel of a cardigan, and nobody has to know which one you're actually wearing.

If you'd rather skip jackets altogether, the replacement is a quarter-zip in merino or a shawl-collar cardigan with a substantial knit. Not a fleece. Fleece pills at the forearms in one winter and reads as gym parking lot.

Buy width before you buy style

Feet spread and flatten with age. The arch drops, the forefoot widens, and the size you wore at forty now squeezes at the ball of the foot while your heel slips.

Get measured on a Brannock device at a real shoe store, standing, both feet, late in the day. Then shop width first. New Balance and Brooks both run 2E and 4E in plenty of models, and so do several dress shoe makers. A wide shoe in your correct length looks normal. A regular-width shoe you've stretched out by wearing looks like a shoe that lost a fight.

Then solve the bending-over problem honestly. Options that don't look medical:

• Chelsea boots. Elastic side panels, pull tab, no laces, and they go with jeans or wool trousers.
• Bit loafers or penny loafers with a leather sole and a rubber topy added at the cobbler for grip.
• Leather sneakers with elastic laces in the same color as the originals. Nobody looks that closely, and you're not tying anything.
• Side-zip boots. A real zipper on the inside ankle, laces left permanently tied.

Skip anything with a giant strip of hook-and-loop across the top. That's the one design that broadcasts itself from across the room, and there's no reason to accept it when Chelsea boots exist.

Fasteners are a design problem, not a character flaw

If small buttons have gotten fiddly, you don't need help. You need bigger buttons.

Have a tailor swap the buttons on your two favorite shirts for slightly larger ones and widen the buttonholes to match. Cost is small, difference is daily. A buttonhook, the little wire loop with a handle, handles cuffs in about four seconds once you've used it twice.

Magnetic closures now exist on shirts that otherwise look completely ordinary, and zippers can be fitted with a leather pull tab that gives you something to grab. The goal isn't to hide anything. It's to stop spending four minutes on a cuff and arriving at breakfast annoyed.

What goes near your face

Skin loses some of its color with age and hair often gains contrast, especially if yours went white or silver. That's an advantage, and beige throws it away. Head-to-toe tan is the single most aging uniform in any closet, because it removes the contrast that used to come from your hair.

Put charcoal, navy, mid-blue, burgundy or forest green in the top six inches of the outfit. Keep the beige below the waist if you like it. A white shirt still works on almost everybody, but a soft blue or a cream is kinder next to thin skin under fluorescent light.

Fabric matters more than it did too. Coarse lambswool that felt fine at forty can feel like steel wool now. Merino at a 17.5 to 19 micron count, cotton jersey with a little weight to it, brushed flannel, cashmere blends. Thin skin also means you get cold earlier, which is an argument for a quilted vest rather than an argument for turning up the thermostat and wearing a sweatshirt to dinner.

One thing that's obviously chosen

Comfort reads as "gave up" only when nothing in the outfit looks deliberate. Fix that with one object, every time you leave the house.

A watch with a leather strap. A belt whose color actually matches your shoes. A pressed collar. A silk scarf, a good hat that fits your head, a pocket square that isn't trying too hard. It takes ten seconds and it changes the read of everything else you're wearing, including the pull-on pants.

Now open the closet and pull out everything you're keeping only because it still technically fits. That's the pile. Somebody younger will be glad to have it.