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One True Pairing: Leather Jackets and Rugged Boots

November 13, 2018

One True Pairing: Leather Jackets and Rugged Boots


Leather jackets and rugged boots have existed as a “look” for decades, popularized by blue collar workers and movie stars like James Dean. While the biker look might first come to mind, this fashion forward look offers many versatile options from bomber jackets to leather suit coats to trench coats.

How to choose a leather jacket?

Pick the type of leather you want to wear. Your choices include full grain leather, suede, shearling, exotic or faux leather. This depends on the look you want to achieve and the situations in which you’ll wear the jacket.

Full grained leather hides mars to it because of the graininess. You won’t notice marks or scratches.

Suede, a brushed leather obtained mostly from lambs, provides a supple yet heavy, material for clothing. It does poorly in wet environments though so don’t wear it in the rain. You can have it treated so it becomes water resistant.

Versatile shearling appears in clothing, carpeting and rugs. It offers warmth and practicality. The leather of shearling comes from recently sheared sheep. It also features the wool derived from the sheep. In clothing, the wool forms the inside of the item; the exterior gets dyed and/or brushed to form suede.

Exotic leather spans numerous animal skins. It ranges from alligator to eel. You’ll see this used in coats and jackets, but also, boots and shoes. Alligator gets used for its durability and looks. The unique grain of ostrich also proves popular. Exotics cost more than other leathers.

Choose faux leather, also called pleather, if you want the look of the real thing, but you’re vegetarian, vegan or simply don’t want to wear an animal. Faux leather has made great strides during the past decade and now so closely resembles the real thing that stars wear it on the red carpet.

Look for quality manufacturing, especially at the seams. Choose a jacket with quality lining that’s securely fastened to the jacket interior.

Try each jacket on to find a comfortable fit. Try to wear an outfit like what you plan to wear most often with the jacket. This lets you get a feel for the look, too. Measure your chest before shopping. If you measure 40 inches at the chest, look for a size 40 or 42. A little leeway works well, but more than a couple of inches over makes the fit too baggy.

Budget conscious buyers can choose a vintage jacket. This also provides the advantage that the piece already got broken in by someone else.

How to choose rugged boots?

Define rugged for yourself. It can mean toughly made work boots or long-lasting design that only needs a touch up to the soles or re-soling every 200 wears or so.

Looks-wise you can choose from tan or beige work boots, black biker boots or combat boots. Each has its own ruggedness.

Attention to detail in design goes a long way to a tough, long lasting boot. Look for a thick, supple leather. It should connect to the sole with stitching or nails, not glue which comes apart easily. Choose rubber or wood heels for a longer lasting wear.

What are the advantages/benefits of pairing a leather jacket and rugged boots?

Pairing a leather jacket and rugged boots opens you to a plethora of looks while keeping you warm and dry. Depending on the shirt or sweater you choose to wear underneath and the pants with which you pair it, you can alter the look from bad boy biker to preppy to punk rocker.

If you pick up a leather jacket with a removable lining, you can extend its wear from early fall through winter and into early spring. Many leather bomber jackets offer shearling linings and some zip out. Some suit coat styles offer the same feature.

What’s the best way to wear leather jackets and rugged boots?

The best look for you makes you feel comfortable. Try any of the following looks to find the right look or looks for you.

Outdoorsy look: Pair the Mount Wilson Bomber Jacket from the Timberland Moto collection with the line’s Echo Lake brown leather side zip boots. Wear a polo shirt and sweater beneath with khakis for a hiker’s outdoorsy look.

Collegiate look: Wear Timberland’s Tenon Leather Field Jacket in Cocoa with a white or gray ribbed t-shirt and dark jeans. Finish the look with the Brewstah side zip boots for a US college campus style.

Biker look: You can channel your inner James Dean with a black leather biker jacket paired with blue jeans rolled up at the ankle just once and a crisp, white t-shirt beneath. Finish the look with black biker boots. Try to find a vintage Schott Perfecto jacket for a classic look.

Punk/rocker look: Copy The Ramones’ look by pairing a few modern pieces. A solid black bomber jacket or a black biker jacket with multiple front zippers works for this look. Wear a solid black short or long sleeved t-shirt underneath. This look works with black or blue jeans. Pair it with combat boots or Doc Martens.

Dressy look: Pair a suit coat styled black or dark brown jacket with a Chelsea boot, popularized in the 1960s by The Beatles. Wear it with khaki or black trousers to match the jacket. A button up dress shirt in crisp white cotton or in a high grade silk works well under the coat.


Whether you want to craft a look all your own or channel your inner Marlon Brando, a leather jacket and rugged boots lets you do it. Leather lends itself to many looks, allowing you to achieve versatility with the purchase of a jacket and a pair or two of boots. Simply by changing the shirt worn beneath the jacket and the pants paired with it, you can achieve multiple looks with one outerwear piece. Leather lasts and keeps you warm making it an ideal choice for fall and winter wear.

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