Tailoring is my favorite, go-to way to dress. It’s flattering and makes me feel cool. But of course, wearing a tailored jacket isn’t practical all the time. Whether it’s hot out or maybe you’re just hanging out casually with friends or at home, here are seven outfit ideas that I personally wear to look sharp when wearing a blazer doesn’t make sense. My other post shares 3 hot-weather outfit ideas. Here are a few cold-weather fits (which are easier, naturally, since you can wear a couple layers).
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Fit 1: The Refined Military Look
Chunky navy turtleneck
Olive/fatigue five-pocket slim-straight pants or chinos
Suede jodhpurs or chukkas
Fit 2: The Youthful Grandpa Look
Navy blue chunky cardigan
Light-wash chambray or denim shirt
Brooks Brothers, Polo Ralph Lauren, Proper Cloth, Anglo-Italian
White or off-white jeans
Sid Mashburn, J.Crew 770 slim straight stretch, Abercrombie, Polo Ralph Lauren
Snuff suede chukkas
Fit 3: The Grown Up Ivy Look
White cutaway collar shirt
Anglo-Italian, Proper Cloth, Kamakura, Spier & Mackay custom
Fine-gauge cashmere sweater (most likely in navy tbh)
Brooks Brothers, Proper Cloth, Polo Ralph Lauren, Sid Mashburn
Light gray flannel trousers
Spier & Mackay, Dapper Classics, Brooks Brothers
Calf tassel or penny loafers
Meermin, Jack Erwin, Beckett Simonon (20% off with code MM20)
Fit 4: The Rule-Breaker Ivy Look
Gray cable knit cashmere sweater
Brooks Brothers, Polo Ralph Lauren
White OCBD
Kamakura, Brooks Brothers, Spier & Mackay
Faded denim
Polo Ralph Lauren, American Eagle original straight, Abercrombie
Snuff suede penny loafers
