These 10 outfits run from linen shirts and tailored shorts in summer heat to cable knits, quarter-zips and a sweater draped over the shoulders once it cools, so the season picks the section to start in.
Fabric changes with the weather, but pleated trousers, a clean fit through the shoulders in a navy blazer or beige one, and a collared shirt under most layers keep the look steady.
1. Cable Knit Sweaters
An olive cable knit over a white collared shirt is a quiet pairing, and the white trousers and white sneakers keep the whole outfit soft instead of heavy. Let the shirt collar sit just above the neckline of the sweater.
I like this version because the single color story does the work. Olive, white, white: nothing competes with the texture of the knit.
Pick a sweater with a clean, even stitch, and keep the shirt plain.
2. Summer Old Money Outfits
Hot weather changes the fabrics, not the formula. A knit short-sleeve polo, tailored trousers with a high waist, and leather loafers still add up to the same polished outfit you would wear in cooler months.
I would pick the polo in a knit with some structure, so it drapes instead of clinging. Tuck it in and let the high rise of the trousers do the rest.
Loafers keep the look dressed. Sneakers would flatten it.
3. Navy Blazer
Few jackets earn their place like a navy blazer, which is why it sits at the center of old money dressing.
Two patterns work together when one is clearly bolder than the other, so keep the stripe and the tie different in scale. I prefer the white trousers in summer; grey or khaki suit cooler weather.
Buy one that fits through the shoulders first, since that is the part a tailor cannot easily fix.
The single most important piece in old money outfits men build around. A properly selected navy blazer works with everything else in your wardrobe and serves every occasion from casual to semi-formal.
4. Linen Shirts
White linen, long sleeves, tucked into light trousers with a dark belt: this is summer dressing at its easiest. The weave breathes, and the creases are part of the look, so skip the iron.
I like the sleeves worn long, which keeps the sun off and looks more deliberate than short ones. Tucking the shirt in and adding a belt keeps the loose fabric looking tidy.
Linen wrinkles by lunchtime. Accept that going in.
5. Tailored Shorts
Tailored shorts should have pleats, a high waist and a cuff, and white linen is the easiest fabric to start with.
Tuck in a linen shirt in a soft color like pink and the shorts read as dressed rather than beachy.
Shorts leave your legs exposed, so a poor fit shows up faster here than on any other piece. The waist should sit high and the hem should land near the knee, never mid-thigh.
I would keep the top simple and the colors soft, as in pink over white. It is a bolder choice than trousers, so it suits warm days and relaxed settings best.
6. Casual Old Money Outfits Men
Dress down without letting go of the standards: a black long-sleeve polo, grey pleated trousers, and a watch make a dinner outfit that needs no jacket.
Fit does the heavy lifting. The polo should skim the body, and the trousers should hang cleanly from the pleats without pulling.
I like a dark top with a lighter grey bottom, because the contrast keeps it from looking flat. Choose quality fabric, since a casual outfit has nothing to hide behind.
7. Pleated Trousers
Cream pleated trousers with a high waist do a lot of quiet work. The pleats add room through the hip and a clean drop to the hem, which reads as more considered than a flat front.
A brown knit polo and brown loafers keep the palette warm and close in tone. I would tuck the polo in so the high rise shows.
Cream marks easily, so it suits a dry day better than a muddy one.
8. Beige Blazer and Navy Trousers
Beige on top and navy below is an easy split, because the 2 colors sit far enough apart to look planned. A white collared shirt between them keeps the contrast crisp.
Dark brown loafers finish the look, and they sit well between a sand-colored blazer and navy trousers because the leather picks up the warmth of the one and the depth of the other.
I would wear the blazer open and skip the tie, which keeps the look relaxed but still dressed.
Buy the blazer to fit through the shoulders, and let the trousers be the darker, plainer piece.
9. Quarter-Zip Over Collared Shirt
A quarter-zip worn over a collared shirt gives you a layer that looks neater than a crewneck and takes less effort than a jacket. Keep the shirt collar flat and outside the zip collar.
Taupe is a good choice because it sits between the white shirt and the grey pleated trousers without clashing with either. I would zip it only partway, enough to show the collar.
Pick a fine-gauge knit, since a bulky one bunches the shirt underneath.
10. Sweater Draped Over Shoulders
Drape the sweater over your shoulders and let the sleeves hang loose in front, with a light knot at most. A red knit against a cream polo and white trousers gives one bright note to an otherwise pale outfit.
I like it best in a color that is clearly different from the rest, as red is here. A braided belt keeps the trousers tidy.
Choose a sweater light enough to stay put. A heavy one slides off the shoulders.
Frequently Asked Questions
What is the old money style for men?
Old money style is quiet, well-fitted clothing in restrained colors and natural fabrics: knitwear, blazers, linen shirts, loafers and simple accessories. It values quality and fit over logos and trends, so the clothes look polished without announcing themselves.
What shoes fit the old money aesthetic?
Start with a pair of dark brown leather loafers: they sit well under sand chinos, cream trousers or a navy blazer, and they take a polish better than almost any other casual shoe.
Suede loafers, boat shoes, plain white sneakers and classic lace-up dress shoes all work too, provided the clothes around them are quiet and fit well. Loafers keep a look dressed, while sneakers can flatten a tailored outfit.
Can you dress old money on a budget?
Yes.
Spend on fit, fabric and color first, and buy basics like Oxford shirts, chinos, loafers, knit polos and simple sweaters before any expensive watch or label. Thrift stores can also turn up classic pieces.
