Dressing Preppy Doesn’t Mean What It Used To: Here’s 4 Ways to Pull It Off This Year

This category may seem like an oxymoron at first, but stick with us. Think of it like this: the clothing is preppy in shape and detail, but those details are more urban than country club – black or grey instead if pastels, slim fits instead of paunchy torsos, or khakis blessedly devoid of pleats.

1. A repurposed tux with casual details


Rare is the black-tie invitation for most men these days, so put your tuxedo to use in new ways. Repurpose it for a night of cocktails by wearing it with a lightweight knit, a silk scarf, and sneakers. It may feel wrong, but it looks so, so right.

Cashmere tuxedo ($1,195) by Hardy Amies; cotton t-shirt ($95) by Sunspel; silk scarf ($115) by Fred Perry

2. A tie with colour can keep you from looking too dour


Just as we praised black dress shoes, we also think the black suit deserves some time in the limelight. If you don’t want to look like you’re attending a funeral (although, honestly, there’s nothing wrong with looking like you’re at a funeral, sartorially speaking), choose a fitted double-breasted jacket and pair it with a tie that has a hint (and only a hint) of colour.

Wool-mohair blend blazer (starting at $4,770) and wool-mohair blend trousers (starting at $1,005) by Berluti; cotton shirt ($505) by Burberry; silk tie ($200) by PS by Paul Smith.

3. Muted colours will let the texture really pop


When picking a tie, a muted colour palette will let the fabric and patterns take centre stage. Wool is a warm and welcoming texture, while crisp silks pair well with the sharp lines of stripes and checks in complementary shades.

(L-R) Cashmere tie ($325) by Brunello Cucinelli, at Harry Rosen; silk tie ($60) by Kenneth Cole Reaction, at Hudson’s Bay; silk tie ($245) by Burberry; silk tie ($195) by Drake’s, at Harry Rosen; silk tie ($120) by Strellson

4. Layer up in unexpected ways


Layering is a big part of this look — but no, we’re not talking about tying a sweater over your shoulders or doubling up on your polo shirts. A turtleneck is this season’s perfect base layer, while an oxford with some light flecks of colour adds a small pop among the varied shades of grey.

Wool coat (price upon request) by Fendi; wool suit ($2,095) by Ermenegildo Zegna; wool button up shirt (price upon request) by Perry Ellis; wool turtleneck ($205) by BOSS.