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Style 5 Days 5 Ways

5 Days, 5 Ways: Leather Pilot Jacket

a live-in-forever type of leather
leather jacket, bomber, flight

by Gabi Updated: June 26, 2022

Products are curated by Style Girlfriend editors. Purchases through our links may earn us an affiliate commission.

If you don’t already have a leather jacket, it’s about time. Leather jackets are timeless, and just about the perfect weight for fall weather. If you’re thinking to yourself, “I’m not that edgy” or “am I really that cool” stop yourself right there – what you’re thinking of is a leather moto jacket. There is another option – the pilot jacket. And it’s just as cool, in a different way.

Unlike the leather moto jacket, there’s no questioning whether or not one can “pull off” the pilot jacket. A chocolate brown leather pilot jacket is like the established, older brother to the black leather motorcycle jacket’s rebellious teenage spirit. The pilot jacket’s basic, utilitarian style easily mixes with every outfit, and looks just as good on a guy who is 25 as a man who is 82.

THE LEATHER PILOT JACKET: SCHOTT, $775

jacket, pilot jacket, flight jacket, bomber jacket, brown, fall, leather, autumn

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A leather pilot jacket is the cool-weather staple that transcends trends and looks amazing at any age.
MONDAY

office style, work style, suit supply, leather jacket, leather pilot jacket

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Suit: Suit Supply, $699 | Shirt: Charles Tyrwhitt, $69 | Shoes: Alden, $550

Tie: The Tie Bar, $19 | Socks:  Ted Baker, $15 | Paste: R+Co, $28

Wear it well: Throw a leather jacket over your suit for chillier mornings.

 TUESDAY

transitional dressing, leather jacket, pilot jacket, schott, vince, cole haan, orvis, man scarf

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Trousers: Vince, $225 | Shirt: River Island, $50  | Chukkas: Cole Haan, $170

Bag: Orvis, $298 | Sunglasses: Ray-ban, $150 | Scarf: Fossil, $60

Wear it well: Bring your favorite summer shirt into fall by pairing it with lots of chocolate brown leather and a cozy scarf.

WEDNESDAY

sweater weather, folk, maison kitsune, schott, leather pilot jacket, boots, boot season, steven alan, miansai, jcrew

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Sweater: Folk, $112 | Chinos: J.Crew, $75 | Boots: Thorogood, $283

Glasses: Steven Alan, $205 | Bracelet: Miansai, $125 | Phone Case: Maison Kitsune, $35

Wear it well: Bring mountain man style into the modern world with slim cuts and fun accessories.

THURSDAY

denim shirt, corduroys, leather jacket, pilot jacket, nixon, new balance, frank+oak, gant

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Corduroys: Beams Plus, $140 | Shirt: Frame Denim, $185 | Belt: Gant, $125

Sneakers: New Balance, $169 | Wallet: Frank+Oak, $38 | Watch: Nixon, $200 

Wear it well: Pick two colors and wear them in every shade and fabric – twice as nice as monochrome.

FRIDAY

leather pilot jacket, wood wood, pilot jacket, travel style, vans, burton, carhartt wip, warby parker, nudie

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Jeans: Nudie Jeans Co., $165  | Tee: Wood Wood, $55  | Sneakers: Vans, $70

Sunglasses: Warby Parker, $95 | Beanie: Carhartt WIP, $45 | Backpack: Burton, $95

Wear it well: Mix and match neutral basics with high-interest accessories.

TELL ME:

WHAT KIND OF LEATHER JACKET FITS YOUR STYLE PROFILE?

Want to see more ways to wear your favorite pieces? We show you how to style the breton shirt, colorful chino and graphic tee, 5 ways.

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Gabi

Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.

More articles by Gabi

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