5 Perfect Combinations for Your Fall and Winter Outfits

The basic building blocks of your personal style are the pairings you wear most often. Think of the shirt and jacket that you can’t help wearing together, the coat and scarf that look like they were made for each other, and the boots and denim that look incomplete without one another.

Add a few more classic combinations to your wardrobe this winter. Our favorites reference the workwear and military heritage that underlies many of the modern man’s most popular pieces of clothing; they manage to simultaneously channel classic aesthetics while adding unexpected, even imaginative twists.

1. A henley and a shawl-collar cardigan

Brooks Brothers Red Fleece henley and Maison Kitsune shawl-collar cardigan

Source: Brooksbrothers.com and Mrporter.com

The shawl-collar cardigan dates back to the 1920s, and in the decades since, has won over many fans for its masterful amalgamation of rakish style and warm comfort — particularly welcome in cool months and chilly climates. In the fall and winter, you can’t go wrong pairing a heavy shawl-collar cardigan, like Maison Kitsuné’s navy blue style, with another casual-yet-charming standby, the henley. With this style, opt for a neutral, like the light gray of the henley from Brooks Brothers’ Red Fleece line, to create a relaxed yet polished look that will pair equally with raw jeans or tan chinos, depending on your agenda for the day.

2. A mariniere and a field jacket

NN. 07 striped wool sweater and A.P.C. cotton field jacket

Source: Mrporter.com

The mariniere became the official uniform of the French Navy in 1858, and Tricots Saint-James began producing the shirts in cotton and wool in 1889. The striped shirt has since been adopted by artists, actors, and style icons. And it’s a style that pairs naturally with another piece with rich military heritage, the field jacket. Choose a hard-wearing but refined field jacket, like A.P.C.’s mid-weight cotton jacket, and wear it with a warm, contemporary version of the mariniere, like NN. 07’s striped wool sweater. It’s a pairing that will easily get you through a Saturday of errands and outings, from the early-morning dog walk to an evening art opening or drinks with friends.

3. Selvedge jeans and work boots

Rag & bone raw selvedge jeans and Oak Street Bootmakers trench boot

Source: Mrporter.com and Nordstrom.com

Workwear devotees the world over consider a pair of rigid, selvedge jeans the gold standard. That’s because selvedge denim is woven on traditional, narrow shuttle looms, as they were in the 1950s. Jeans have been a staple in the wardrobes of working men since the 1800s, and they’re just as crucial to guys now. You can honor the workwear origins of your favorite pair of jeans by wearing them with work boots. With denim like Rag & Bone’s raw selvedge jeans and a good pair of boots like Oak Street Bootmakers’ trench boots, you’ll have an unbeatable duo of time-tested style and hard-wearing construction — and both items will only look better with age.

4. A chambray shirt and a cotton-canvas jacket

Brooks Brothers chambray sport shirt and Filson cotton-canvas cruiser jacket

Source: Brooksbrothers.com and Mrporter.com

The chambray shirt is a workwear staple that was adopted by the U.S. Navy in 1901. In recent years, the popular resurgence of workwear styles has brought it back with a vengeance. A good chambray shirt is a versatile piece that you can wear as easily with a dark blazer as with a more casual topper. For a timeless pairing, pay homage to chambray’s workwear roots by wearing a slim chambray shirt, like Brooks Brothers’ Red Fleece sport shirt, with a cotton-canvas jacket, like Filson’s tan cruiser. It’s a perfect look for autumn’s warmer days, and you can add a simple crewneck sweater over the chambray when the days get colder.

5. A black sweater and a brown leather jacket

S.N.S. Herning waffle-knit wool sweater and Schott A2 leather flight jacket

Source: Mrporter.com

For particularly cold or rainy weather, nothing beats a chunky sweater to protect against chills. But what to pair the classic black sweater with? A brown leather jacket, of course. This is a prime example of how the best ensembles can — and often should — violate so-called rules, like the nonsensical prohibition of wearing black with brown.Choose a textured black sweater, like the waffle-knit wool sweater from S.N.S. Herning, which has been making wool sweaters since the 1920s. Pair it with a timeless leather jacket, like Schott’s A2 leather flight jacket, which is modeled after a jacket designed in 1951, for a look that keeps a soft sweater looking sharp.

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