When the temperature drops, your outerwear becomes the most important piece of your outfit. It’s the first thing people see, and it sets the tone for your entire look. A great jacket or coat does more than just keep you warm; it ties everything together, adding a layer of style and personality. For those of us who lean into a vintage-inspired aesthetic, the right outerwear is a chance to make a real statement.

Forget fleeting trends that are gone in a season. We're talking about timeless pieces that have been cool for decades and are having a major moment right now. These are the jackets and coats that blend classic design with modern fits, giving you a look that feels both authentic and current. From the rugged utility of a chore coat to the sleek lines of a bomber, this season's trending outerwear is all about pieces with history.

Let's break down the essential outerwear styles you need in your closet, how to wear them, and where you can find some great new versions with that perfect retro feel.

The Chore Coat: Workwear Turned Style Staple

The chore coat is a masterpiece of functional design. Originally created in 19th-century France for laborers, farmers, and railway workers, it was built to be tough, practical, and easy to move in. Typically made from durable cotton canvas or denim, it features large patch pockets, a simple button front, and a classic collar. Its beauty lies in its simplicity and ruggedness.

Today, the chore coat has moved from the workshop to the wardrobe. It’s the ultimate transitional jacket, perfect for those in-between days of fall and spring. Its boxy, slightly oversized fit makes it great for layering, and its utilitarian roots give any outfit an instant dose of understated, vintage cool.

How to Style It

  • Modern Workwear: Lean into the coat’s heritage by pairing a classic navy or khaki chore coat with some straight-leg jeans, a simple henley, and a pair of sturdy work boots. It’s a clean, masculine look that’s both stylish and practical.
  • Layered and Textured: Use the chore coat as your go-to layering piece. Throw it over a hoodie or a chunky knit sweater for added warmth and visual interest. This works especially well with corduroy pants for a look full of rich textures.
  • Smart-Casual: A chore coat can be dressed up. Choose one in a dark color and wear it over an Oxford cloth button-down with some tailored chinos. It acts as a more casual, interesting alternative to a traditional blazer.

Where to Find Them

  • Carhartt WIP Michigan Coat: Carhartt is a legendary workwear brand, and their WIP (Work in Progress) line refines their classic designs for a modern audience. The Michigan Coat is an icon, offering incredible durability and a timeless look.
  • Taylor Stitch The Ojai Jacket: This brand is known for its responsibly built, classic menswear. The Ojai Jacket is their popular take on the chore coat, often made from unique fabrics like organic cotton or moleskin and featuring cool details like ring-back buttons.
  • Everlane The Chore Jacket: For a minimalist and sustainable option, Everlane’s version is made from durable organic cotton with a clean, modern fit. It’s a versatile piece that aligns with a conscious mindset.

The Bomber Jacket: Military Cool, Civilian Staple

The bomber jacket, also known as a flight jacket, has a rich history as military-issue gear for pilots. From the leather A-2s of WWII to the nylon MA-1s of the 1950s, these jackets were designed for warmth, mobility, and function in the cockpit. Characterized by a cropped length, ribbed cuffs and hem, and a front zip, the bomber has become one of the most iconic and versatile jackets in menswear.

It was adopted by countless subcultures over the decades, from 60s mods to 80s punks, and it remains a symbol of rebellious cool. A good bomber jacket adds a sharp, clean-lined silhouette to any outfit, making it a perfect piece for both casual and slightly dressed-up occasions.

How to Style It

  • Effortless Weekend Look: The easiest way to wear a bomber is to throw it over a simple crewneck t-shirt (white, black, or grey) and pair it with your favorite jeans and sneakers. A classic sage green or black nylon bomber is perfect for this.
  • Elevated and Sleek: For a night out, opt for a bomber in a more luxurious fabric like suede or wool. Pair a black or brown suede bomber with dark trousers, a fine-gauge knit sweater, and some Chelsea boots for a sophisticated, modern look.
  • Vintage Inspired: Nod to the jacket’s heritage by pairing it with other classic pieces. A leather bomber jacket with a knit polo, pleated trousers, and loafers creates a sharp, mid-century-inspired outfit.

Where to Find Them

  • Alpha Industries MA-1 Bomber Jacket: Alpha Industries was one of the original military contractors for the MA-1, so this is as authentic as it gets. Their jackets are built to last and feature the iconic orange lining.
  • Schott NYC Leather Flight Jacket: If you're looking for a timeless leather bomber, Schott NYC is a legendary American brand. Their flight jackets are an investment piece that will last a lifetime and only get better with age.
  • J.Crew Bomber Jacket: J.Crew offers bombers in a variety of fabrics and updated fits. They often have options in wool, nylon, or cotton blends that are perfect for a smart, preppy take on the military classic.

The Wool Overcoat: Timeless Elegance

When the weather gets truly cold, nothing beats a classic wool overcoat. This is the most formal piece on our list, but its versatility might surprise you. An overcoat is a long, heavy coat designed to be worn over other clothing, providing a final, warm layer of protection. Styles range from single-breasted Chesterfield coats to double-breasted peacoats, but a simple, single-breasted topcoat is arguably the most versatile.

Once reserved for wearing over suits, the modern way to style a wool overcoat is to mix it with casual pieces. This high-low approach creates a look that is sophisticated yet effortless. A well-fitting overcoat in a timeless color like camel, charcoal, or navy will instantly elevate everything you wear underneath it.

How to Style It

  • Casual Sophistication: This is the best way to wear an overcoat today. Throw a camel-colored coat over a casual outfit like a hoodie, relaxed-fit jeans, and some retro sneakers. The contrast between the formal coat and the casual clothes is incredibly stylish.
  • Smart and Layered: For a look that’s perfect for a creative office or a nice dinner, layer your overcoat over a turtleneck sweater and some wool trousers or dark chinos. It’s a warm, textured, and incredibly sharp outfit.
  • Weekend Walks: A dark charcoal or navy overcoat looks great with more rugged pieces, too. Try it over a chunky fisherman sweater, worn-in denim, and a pair of sturdy leather boots.

Where to Find Them

  • Todd Snyder Italian Wool Topcoat: Todd Snyder excels at creating luxurious versions of American classics. His topcoats are often made from beautiful Italian wool and feature a perfect, modern fit that can be dressed up or down.
  • COS Tailored Wool Coat: COS is known for its minimalist, architectural designs. Their wool coats are clean, sharp, and often have a slightly oversized fit that is perfect for modern layering.
  • Banana Republic Italian Melton Topcoat: A fantastic and accessible option for a high-quality wool coat. Banana Republic consistently delivers classic, well-made outerwear in beautiful fabrics that look far more expensive than they are.