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

01-An-Informal-Affair

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

02-Classically-Cool

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

04-Stripe-Right

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

03-Greys-Anatomy

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.