How to style wide leg trousers: choose the shoe first

To style wide leg trousers, choose the shoe first, hem the trousers to it, then keep the top short or close. Paul Poiret cut wide trousers for women in 1913, and the hem still decides how they look.

Katharine Hepburn, who wore trousers when that was a radical move for a woman, put it plainly: "the thing that drove me out of skirts was the stocking situation". Wide trousers settle the stockings and leave one question, the shoe.

The order matters because a hem is set from the floor up, and a hem let back down can show its old crease. So one pair is cut for one kind of shoe. Buy the trousers with the shoes you will wear most, and take those shoes to the tailor.

Quick facts

• Wide leg pairs on within: 36, from 23 designers at 3 boutiques, read 2 October 2026.
• Price range: CAD 149 to CAD 1,645, with a median of about CAD 765.
• Women's and men's: 23 women's, 9 men's and 4 listed for neither.
• In the suit edit: 23 of the 36 pairs.
• Oxford bags in the mid 1920s: 22 to 23 inches round the bottoms, later 44 or more.
• Pleats Please, since 1993: pleated after it is cut and sewn, the reverse of the usual order.

With a heel or a heeled boot: the long hem

A heel lets the hem fall close to the floor without touching it. Nina Ricci's flared pair is the grand one: black wool with a bow, CAD 1,580. MM6 Maison Margiela does a black pinstripe at CAD 995, and Coperni's green wool pair has dropped to CAD 449 from CAD 895.

Le Smoking, Yves Saint Laurent's tuxedo for women in 1966, cut its trousers to lengthen the leg, and a heel under a long hem does the same work. Under them, try MM6's black calf Anatomic ankle boot at CAD 1,350, or Guidi's 796ZI, which zips up the back on a metal heel (CAD 2,050). More heeled pairs sit in women's boots.

With a flat or a derby: the shorter hem

With a flat, cut the hem shorter, so it brushes the shoe instead of the street. UJOH's sand belted wide pant is 100% wool at CAD 1,020, and UJOH has 45 pieces in all. Undercover's wool blend wide leg pants are down to CAD 749 from CAD 1,095.

Pleats move. Pleats Please Issey Miyake, launched in 1993, cuts and sews each piece before pleating it, the reverse of the usual order, and the clothes give an unusual freedom of movement. Its thicker pleated flared pants in beige are CAD 780.

Palazzo pants, a trend for women from the late 1960s, flare evenly from the waist to the ankle; bell bottoms stay snug until the knee. Over a flat, the cut from the waist is the easier one to wear. Guidi's black leather Classic Derby 792Z, CAD 1,375, is the flat shoe for it.

Buy the shoes first. The trousers are cut for them.

For the top half: short, close or a waistcoat

Wide trousers take a top that is shorter or closer than they are wide. Patou's tailored short jacket in praline is CAD 899, down from CAD 1,875. A waistcoat worn alone does the same job (INTO THE EAST's black stand collar vest, wool and silk, is CAD 780).

A short jacket over a wide trouser is a suit with the proportions turned around. In the suit edit, the two hang side by side with waistcoats, and Litkovska's black wool blend vest there is CAD 1,100. For the office, the Business casual lens puts tailored trousers with shirts and loafers.

For men: Oxford bags were theirs first

It is said that Oxford bags began with a 1924 ban on plus fours at lectures, and that students hid the plus fours underneath. Wikipedia doubts it: the early bags were not wide enough to manage it. In the late 1920s Lindy Hop dancers at the Savoy Ballroom in Harlem took them up, and Fred Astaire wore them on screen.

UJOH's black Tape Belt 1 Tuck pants are 100% wool at CAD 875, and Avavav's black Petra suit pants are CAD 660. Sies Marjan's pressed wool pant with a side stripe is down to CAD 329 from CAD 1,250. Men's pants runs to 306 pieces.

Before you buy

Our note on where to get designer pieces altered gives the rule: bring the shoes you will actually wear, since the hem is set from the floor up. Hems are routine work (what a tailor can alter), but on worsted wool an old crease rarely disappears.

The designer shop in Yorkville, which has 29 of the 36 pairs, gives exchange or store credit within 14 days on pieces unworn and unaltered. So try them on with the shoes before the tailor touches them. Due West takes unused pieces back within 30 days, except sale pieces.

Wide trousers went from the lecture hall to the dance floor and the dinner table (see date night outfits). The shoe still decides how they look.

Common questions

What tops look best with wide leg trousers?

A top that is shorter or closer than the trousers are wide: a cropped jacket, a waistcoat, a tucked shirt or a fitted knit. Patou's tailored short jacket in praline is CAD 899, down from CAD 1,875.

What shoes to avoid with wide leg pants?

Any shoe the hem was not cut for. A flat under trousers hemmed for a heel lets the hem drag on the ground, and a hem cut for a flat sits high over a heel.

Are wide leg pants out for 2026?

Not at the boutiques: on 2 October 2026 they held 36 pairs of wide leg trousers on within, from CAD 149 to CAD 1,645. Of those, 23 sit in the suit edit, beside its blazers and waistcoats.

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