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Navigating transitional weather in style means knowing how to layer clothes for everyday wear and rugged adventures alike. Like changing your oil and casting upstream, knowing how to layer up for any forecast (and every occasion) is a skill worth having. From a clean and classic combo to a work-ready getup, we're here to help with our handy field guide to layering in any season.

Clean & Classic

Whether it’s a weekend outing or a night on the town, a cardigan sweater is a timeless layering piece that adds class and curb appeal to any outfit. We recommend keeping it simple with a classic tee and some well-tailored chinos or selvedge denim jeans for a fit that’s 100% trend proof.

Model wearing The Crawford Sweater with selvedge jeans

Rugged & Refined

A great way to look sharp when you’re saddling up to either the bar or the dinner table is to build your look around a statement piece like a Bomber Jacket. Add an oxford shirt and some selvedge denim for a considered ensemble that’s far from stuffy.

A green oxford shirt layered beneath a bomber jacket

Tough & Timeless

For a classic, casual look that’s ready to put in the work, you can’t go wrong with a shirt jacket. Not only is it versatile and durable, but since it breaks at the hip, the style makes you appear taller (we’ll take it). We like to pair ours up with a simple button up shirt and some sturdy work pants (like our Chore Pant) for a timeless workwear look.

Model wearing The Lined Utility Shirt with Chore Pants

Insulated & Impervious

A great way to add insulation and visual intrigue is to layer a versatile cotton sweater under a chore coat or trucker jacket. The textured base layer draws the eye in and keeps you warm while a tough top layer fends off the elements. Finish the look with some trusty chinos for an outfit that looks great just about anywhere, and is ready for anything.

Model wearing The Long Haul Jacket with a sweater

Brave The Elements

When it comes to being ready for outdoor adventures, a classic pullover layered beneath a rugged jacket is sure to keep you equipped. Pair it with a water repellent windbreaker for an outfit that fears no forecast, or throw on a denim jacket and chinos for a hard-wearing look that’s ready to go around town.

Model wearing The Long Haul Jacket with a sweater

Now that you have everything you need to ace any occasion, check out our roster of versatile pieces to see you through winter, spring and countless seasons to come. Happy layering.

Shop Layering Essentials

fit model posing in The Ryder Jacket
November 06, 2025

How to Style Trucker Jackets

Some pieces earn their reputation the honest way—through decades of use, refinement, and reinvention. The trucker jacket is one of them. Born from the needs of labor and loved for its timeless versatility, it’s become a fixture of men’s outerwear for over half a century. Short and structured, tough but never heavy-handed, it’s the kind of layer that can slot into anyone’s heavy rotation without a second thought.

Read more
fit model posing in wool sweater
October 31, 2025

The Hardworking History of Wool

Long before wool became a mark of refinement, it was a material of necessity. Shepherds, sailors, and tradesmen relied on it not for fashion, but for survival—a natural fiber that kept them warm in the damp, breathed through the heat, and held its shape through seasons of labor.

Over centuries, that same grit became the fabric’s greatest luxury. Today, wool still carries the soul of its workwear past, but with a polish that earns it a place in any modern wardrobe.

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