7 Classic Jackets That Will Be Your Favorite Fall Staples

The height of summer seems to have finally passed, and with it the awful heat that keeps you from wearing anything but the most lightweight of clothing. One of the best things about dressing for fall is finally getting to wear layers, and shopping for a new jacket (or two) is one of the most fun ways to prepare your wardrobe for fall. Below, we’ve rounded up seven of the best, classic styles of jackets for you to consider for the season ahead.

Bomber jacket

Ralph Lauren quilted bomber jacket

Source: Ralphlauren.com

The bomber jacket is a simple, lightweight jacket that looks eternally cool layered over casual ensembles for fall. You can find a bomber jacket at almost every price point and in almost any material, from twill to nylon to leather to wool. A great example of the style is Ralph Lauren’s quilted bomber jacket, which is water-resistant thanks to its sleek nylon exterior. Another stylish iteration is the bomber jacket from Brooks Brothers’ current Red Fleece Collection, which is a great choice for slim guys thanks to its trim, modern fit.

Denim jacket

RRL Kenney denim jacket

Source: Ralphlauren.com

The denim jacket is a staple of American workwear, and generations of cowboys, farmers, miners, and other hard-working men have honed the art of the worn-in denim jacket. A jacket cut of high-quality denim and adorned with minimal details is an excellent layering piece that you’ll love for casual outings and weekend errands. You have a couple of options when shopping for a denim jacket. You can go with a high-end piece that pays homage to the quintessential denim jacket cut, like the RRL Kenney jacket constructed of eight-ounce Japanese denim. Or go straight to the source with a piece by Levi’s, the name that everyone associates with denim jackets. The brand’s trucker jacket is a classic style that you can’t go wrong with, whether you choose a distressed and worn-in blue or a sleek, classic black.

Field jacket

Alpha Industries slim M-65 field jacket

Source: Amazon.com

A field jacket is a classic style passed directly on to today’s guys from generations of military uniforms. The field jacket is a great casual style that pairs well with everything from a tee and jeans to a more buttoned-up oxford shirt and a pair of tan chinos. You can still buy the authentic M-65 jacket from Alpha Industries, the original producer of the style, either in a classic, standard fit or in an updated slim fit. (Either way, it’s wise to size down with this jacket, since it was originally designed to fit over bulky military uniforms.)

Leather jacket

Ralph Lauren leather motorcycle jacket

Source: Ralphlauren.com

A good leather jacket is an undeniable staple that deserves a place in every cool guy’s wardrobe. The styles of leather jackets are practically endless and almost exclusively vintage-inspired, including the flight jacket, double rider motorcycle jacket, and cafe racer jacket. A great option is Ralph Lauren’s undeniably cool leather motorcycle jacket, which already looks worn-in in the best way possible. Schott’s A2 flight jacket is another unbeatable choice, and takes its cues from an authentic jacket from 1951. As you’ll likely notice while shopping, good leather jackets are generally pretty expensive, and the leather used to make cheaper jackets don’t usually hold up to heavy wear particularly well. If you’re looking for a great deal on a leather jacket, consider going vintage.

Shirt jacket

Filson Cruiser Mackinaw wool shirt jacket

Source: Mrporter.com

For particularly chilly nights, a wool shirt jacket is a dependable option. A shirt jacket in heavy wool and a reasonably trim silhouette will look as appropriate for a rooftop gathering at your coworker’s downtown apartment building as for a weekend trip to your best friend’s remote cabin. Filson’s Cruiser jacket, made of water-repellant Mackinaw wool, is about as classic as shirt jackets come. Billy Reid’s Trey shirt jacket expertly exemplifies the intersection of rugged and refined, for which a shirt jacket is so perfect, with a blue dégradé effect for a contemporary twist on the all-American style.

Sport Coat

Brooks Brothers Harris Tweed sport coat

Source: Brooksbrothers.com

Most guys should own multiple sport coats, but fall is an especially great time for the style because it offers the opportunity to wear a sport coat in herringbone or tweed, or even in patterns like checks, tartans, and plaids. One name that will constantly come up if you’re looking for the perfect fall sport coat is Harris Tweed, which is woven in Scotland and has been a respected name for generations. Try on some Harris Tweed for size with this windowpane sport coat from Brooks Brothers, or go with wool sourced from a British mill with Ralph Lauren’s tick-weave sport coat. Both are classic options that manage to look both distinguished and modern, perfect for the guy who wants to look sharp while enjoying the cool weather.

Waxed canvas jacket

Belstaff Trialmaster waxed canvas jacket

Source: Mrporter.com

If you live in a city that’s particularly rainy, then a waterproof jacket should be high on your shopping list for fall. There’s no better intersection of form and function than a waxed canvas jacket, and you can’t go wrong with a classic by Barbour or Belstaff. Belstaff’s Trialmaster is perhaps one of the most iconic jackets in the category, and is the first waxed cotton, four-pocket jacket that the label ever made. Other rugged options from Belstaff include the Tourmaster and the Roadmaster. Another classic name in the waxed-cotton business is Barbour, which offers the popular Bedale jacket in black, navy, or olive, perfect for coordinating with all of your favorite fall ensembles.

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