Use these 11 Items to Build 56 Looks

Your cheat-sheet for being better dressed this season, whatever the weather

It’s the most wonderful time of the year — those awkward few months we call autumn and fallen leaves aside, they also provide every man the chance to spruce up his wardrobe and prepare for winter. Think layering, closed-toe shoes with solid soles, heavy knits, jackets and most importantly, getting more mileage out of what you already have.

Whether you’re planning to start anew or simply update your existing arsenal, here’s some style inspiration for the weeks ahead. With only 11 key items, you can create 56 looks — each one as sharp as the next. Scroll down to see how we’ve solved transitional style for you.

For warm-ish weather

transitional dressing for warm weather

It’s time for your sleeves to go beyond your biceps. Go for tops you can layer over and under each other. Our recommendations for your rotation: a utility overshirt for something hard-working, a check button-up for smartening up and a long-sleeve T-shirt for your off-duty looks. These should be easy to mix and match with versatile, good quality pants like dark jeans, khaki chinos or plain joggers. If you’re looking for long-lasting investment pieces, keep the fit somewhere between slim and straight, so they’re suitable for dressing up or down.

For days in the low-20s

Transitional dressing for cooler weather

Things are cooling down, the sun sets earlier and waking up is a bit harder. That means it’s time to up your layering game. Start flexing in a neutral colour palette and play around with combinations of your jeans, chinos and shirts. Pieces like hoodies and denim jackets also make for great outer layers, so throw them on over a T-shirt.

For Netflix-and-chillingly cold nights out

transitional dressing for cold weather

Bundle up and feel free to add on a scarf and beanie. As actual winter starts rushing (or raining) in but your social calendar isn’t emptying itself up, you should be wearing even more layers. The age-old practical rule still applies: wear your lighter fabrics closer to your body, then stack on heavier ones with each layer. Try most street style king’s go-to look: a hoodie under a bomber or smarten up your denim jacket with a button-up shirt. And start wearing your boots a lot more — getting mud will be easier with them than with white sneakers.

winter starter pack