The ideas here run from a pinstripe suit with a turtleneck to a quarter-zip fleece with chinos, and the right pick depends on how much structure you can stand around your neck and shoulders.
If a collar and knot feel like a choke, go with the knit polo, the denim shirt or the turtleneck.
For a sharper line, a blazer in navy, beige or grey does the job, and each one pairs with trousers or jeans without much fuss.
1. Well-Fitted Tailored Clothes
Fit does more for a suit than fabric or price. Shoulder seams should sit where your shoulders end, and the jacket should close without pulling at the button.
A green pinstripe like this one shows every flaw, because the stripes bend wherever the cut is off. I would pick one good tailor and bring the suit back for small changes before wearing it out.
A tie in a quieter pattern than the suit works best here, with a plain pocket square to keep things calm.
2. Blazer with Cream Trousers
Cream trousers calm a loud jacket. A brown houndstooth blazer already has a lot going on, so keep everything under it plain: a denim shirt in one even blue, open at the collar, and trousers in a single light shade.
I like this for men who find a full suit stiff. The pattern up top gives it interest, and the cream keeps it from looking heavy.
Stick to leather shoes in brown and the colors stay in one family.
3. Blazer with Jeans and Neck Scarf
A blazer in light blue reads as casual, which is why it works over a white t-shirt and blue jeans. The neck scarf is the detail that makes it look planned rather than thrown together.
Keep the scarf patterned and the rest plain. A woven belt and clean sneakers finish it without adding another statement.
I would skip anything baggy here. Jeans that fit close to the leg and a blazer that actually fits across the shoulders keep this from looking like you’re dressing younger than you are.
4. Navy Blazer with White Trousers
Navy and white is about as safe as a combination gets, and a light blue button-down sits between them without any effort. A brown leather belt finishes the look, and nothing else is required.
White trousers are the one risk. Pick a heavier weave so they don’t show through, and keep them for warm days and daytime events.
My preference is to leave the blazer unbuttoned and the shirt collar open. It looks relaxed but still put together.
5. Beige Blazer with Navy Trousers
Beige against navy is a softer pairing than the usual dark suit, and it suits a man who wants to look dressed without looking severe. A white shirt and navy tie hold the whole thing together.
Match the navy of the tie to the trousers so the beige blazer is the only light piece up top. Light beige loafers carry the tone down to the shoes.
I would choose this for daytime events, since it looks wrong after dark.
6. Grey Blazer with Navy Trousers
A textured grey blazer gives navy something to push against. Worn over a navy crewneck with navy trousers, it makes a tone-on-tone base, and the jacket supplies the variety.
I prefer a fine-knit sweater here, since a bulky one fights the blazer’s cut. Brown leather boots add warmth, and they keep the grey and navy from going cold.
It is an easy outfit for a normal workday, with no tie to manage.
7. Polo Shirt with Trousers
A knit polo tucked into dark trousers is a good answer for men who find a dress shirt stiff but don’t want a t-shirt.
The knit has more texture than a standard polo, and the tuck gives it a finished line.
Keep the polo in a neutral shade and the trousers dark, so the contrast does the work. I’d add a plain leather belt and leave it there.
Choose a polo that skims the stomach instead of clinging to it.
8. Denim Button-Down Shirt
A light blue denim shirt worn open is an easy layer, and I like it most when nothing else competes with it. Under it, a plain white or gray tee keeps the look clean.
Pick a wash that stays light and even, since heavy fading looks worn rather than chosen. Sunglasses in a dark frame sharpen it without any extra effort.
Leave the shirt unbuttoned on a warm day and fasten it on a cooler one. It works either way, and the collar should lie flat.
9. Quarter-Zip Fleece with Chinos
Black quarter-zip over a light base sits comfortably between sporty and neat. Pair it with light chinos and brown leather boots, and the outfit reads as deliberate rather than a gym leftover.
Fit decides this one.
A fleece that hangs loose at the waist looks sloppy, so choose one that ends near the belt line. Chinos should be trim through the leg without pulling.
A baseball cap suits a casual day. I’d drop it for anything where you want to look dressed.
10. Pinstripe Suit with Turtleneck
A dark pinstripe suit with a turtleneck in place of a dress shirt drops the tie and keeps the sharp cut. It looks modern, and it’s a good fit for men who feel choked by a collar and knot.
Keep the turtleneck in a dark, solid color so the stripes stay the only pattern. A fine knit sits better under a jacket than a thick one.
The suit has to fit well, since nothing at the neck distracts from the shoulders.
Confidence in Dressing
Confidence shows up in how an outfit is worn, and it counts for more than any single piece.
A man who feels good in what he has on stands straighter, moves easier and looks better than one who is adjusting his collar all night.
So choose clothes that suit your own taste, not what a stranger thinks you should wear. If a jacket makes you feel like yourself, it will look better on you than a "correct" one that feels like a costume.
A simple test: put the outfit on and forget about it for an hour. If you stop noticing it, keep it.
Avoiding Trends
Trends are mostly built for younger men, and a few of them work against you past 50.
I would skip skinny jeans, ripped or heavily distressed denim, loud graphic tees, chunky logo trainers, ultra-skinny ties and pleated baggy trousers. Head-to-toe black is also easy to get wrong.
Build the closet around pieces that never date: one pair of leather dress shoes, a navy blazer, and dark jeans that fit well. Buy the best you can afford and wear them for years.
I would still watch trends lightly.
Small shifts in silhouette, color or detail keep an outfit current without making it a costume. A jacket that sits flat across the shoulders and a waist that skims your torso will look sharper than whatever is trending this season.
There has never been a better time to be a guy in his 50s who wants to dress well.
— Esquire
Dress Codes
When a host invites you to an event, the dress code is part of the invitation. Follow it, even if your own style leans another way.
Dressing the part is a form of respect for the person or place hosting you. It also helps you, since you walk in knowing you belong and can stop thinking about your clothes.
If the code is unclear, ask the host. Past 40, a man should be able to switch into formal dress when the occasion calls for it, and having one outfit ready makes that easy.
Frequently Asked Questions
How should a 55 year old male dress?
For a man in his mid-50s, I’d build around dark jeans or slim chinos, a knit polo or fine-gauge crewneck, and a navy or gray blazer when the day calls for more.
Mid-weight fabrics hang better than thin ones. Price tag aside, the shoulder seam should land right at the edge of your shoulder, and the body of the jacket or shirt should skim your torso without pulling.
How to dress for 50 degree weather for men?
Layer a fine-knit sweater under a blazer, such as a navy crewneck with navy trousers and a textured grey jacket. Brown leather boots add warmth and keep the grey and navy from looking cold.
