Old money outfits for men start with the jacket

Old money outfits for men come down to 4 pieces: a knit polo, pleated trousers, a Harrington jacket and loafers. Across the old money edit, 225 pieces for men range from CAD 125 to CAD 9,500.

Buy the jacket first. Baracuta still makes the G9, its original Harrington, and a navy one is CAD 795 at Due West. A knit polo starts at CAD 109, and it is a fine place to start too.

A G9 is waist length with a two button collar and a Fraser tartan lining, so it frames a polo the way a golf jacket should. A hoodie hides the polo, and the outfit stops there.

Quick facts

• Stock on within: 225 men's pieces across 52 designers, read 9 October 2026.
• Price range: CAD 125 for a knit vest to CAD 9,500 for a quilted flannel jacket.
• Median price: CAD 700 across the edit.
• Under CAD 300: 43 pieces on the shelves.
• Second hand supply: 15 pieces, 11 pre owned and 4 lightly used.
• Men's departments: 304 pants, 255 pairs of shoes, 33 sweaters, 33 suits and blazers.

For the weekend under a Harrington

Start with the jacket. The navy Baracuta G9 jacket from Baracuta costs CAD 795 at Due West across five sizes from 38 to 46. The G is for golf, and Due West's listing adds a back vent cut so rain runs off.

Beneath it, Les Deux makes the ivory Signature knit polo in cotton with a knitted pinstripe for CAD 259. Two friends founded the label in Copenhagen during 2011. Add the eggnog white Romeo pleated chinos at CAD 159 and the brown croco mix boat shoes at CAD 369.

That puts the weekend total at CAD 1,582.

For dinner in Sea Island cotton

Dinner is a knit polo. Sunspel has made clothes in England since 1860, and toward the end of that century it began using Sea Island cotton, a cotton with very long fibres. Lindy Hemming, the costume designer, tailored Sunspel's Riviera polo to fit Daniel Craig for Casino Royale in 2006.

Due West has Sunspel's navy Sea Island cotton knit polo for CAD 380, with one left in XL. Pair it with Les Deux's asphalt grey Randall pleated trousers, half wool, at CAD 115. Gucci's black leather Princetown slipper is CAD 800 at the resale shop, one pair in 9M.

Dinner comes to CAD 1,295.

For the cold in Glen plaid and rib knits

Then the cold. Glen plaid began in the 1840s when the Countess of Seafield dressed gamekeepers on her Glenurquhart estate. King Edward VII made it famous when he was Prince of Wales, and Cary Grant wore a grey suit in it in North by Northwest (1959).

Drôle de Monsieur cuts brown Prince of Wales check golf trousers with pleats for CAD 545. The cloth is only 12% wool, so a reader who wants more wool takes the Randall pair at CAD 115, which is half wool. Under COOR's grey double breasted coat at CAD 825, wear Les Deux's ivory merino rib roundneck sweater at CAD 279, one of 33 men's sweaters.

Pre owned Louis Vuitton Monte Carlo moccasins add CAD 500 in size 8.5 at the resale shop. The cold costs CAD 2,149.

For the water in tailored swim shorts

Swim shorts can be tailored too. Adam Brown and Julia Simpson-Orlebar founded Orlebar Brown in 2007 and cut its swim shorts on the 17 piece pattern of a pair of suit trousers. Their navy Bulldog swim shorts cost CAD 395.

Buy the jacket first: a G9 shows the polo, a hoodie hides it.

Above the waist, wear Sunspel's navy Riviera cotton mesh polo for CAD 230. Les Deux's brown boat shoes, embossed leather with a suede toe, are CAD 369. Paul Sperry made the first pair in 1935, after noticing his dog could run across ice without slipping, and cut grooves into the soles.

(Wikipedia says boat shoes are partly a status symbol, because owning a boat is tied to wealth.) That brings the waterside total to CAD 994.

Before you buy

There is no Ralph Lauren, Brooks Brothers or Lacoste on within. The old names sit second hand at Utopia, 132 Cumberland Street, Toronto, where every sale is final. A pre owned Hermès crewneck is CAD 300 in size M, and a pre owned Tiger of Sweden blazer in mink is CAD 100 in size 46.

Due West at 431 Queen Street West in Toronto refunds unused regular priced pieces within 30 days. Shipping runs CAD 45 to the continental US and CAD 99 to Western Europe, with import duties paid by the buyer. Most pieces here come in one to five sizes, so check the size first.

When Lisa Birnbach poked fun at this wardrobe in The Official Preppy Handbook in 1980, the joke helped bring it back.

Common questions

How to dress old money men casually?

Wear a green knit polo, white pleated chinos and brown boat shoes: CAD 637 for all three, from Les Deux. The Emmanuel polo is linen and cotton at CAD 109, and the Romeo chinos are CAD 159. The boat shoes are CAD 369.

What is the old money style for men?

Old money style for men is the Ivy League and prep school wardrobe: navy blazers, oxford shirts, polo shirts, grey flannel trousers and loafers. Ivy style began in the early 1900s and was widespread by the late 1950s. The old money edit has 225 men's pieces, from CAD 125 to CAD 9,500.

What is the old money aesthetic called?

It is called preppy, or Ivy style. Preppy comes from the prep schools, and Ivy from the Ivy League colleges. Lisa Birnbach's The Official Preppy Handbook poked fun at it in 1980 and fed a revival.

within carries the world's best boutique shelves. Toronto is open now and more cities follow. The quizzes will read your taste.