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Expert Advice: The Art of Winter Layering

Hint: leather jacket

In our style column, Jess Kirby of Prosecco and Plaid styles her boyfriend, Craig, in winter layers, including the ideal jacket for winter.


It doesn’t get much cooler than this. With it’s vintage look, quilted detail and warm layer of insulation, the Skye Peak Quilted Leather Jacket is the ultimate cold weather outerwear essential. It’s thick enough to keep the cold out but still has a slim fit.


Living in a coastal climate, the weather is unpredictable so layering is a way of life. For our active and outdoor lifestyle, Craig and I both like to wear pieces that are functional but also look good. Having both lived in major cities, our style is influenced as much by New England as it is by the laid back vibes of LA and the no fuss, minimal style of New York City.


As a photographer, Craig is always carrying around equipment and running to and from locations. His style is pretty casual and minimal so this leather jacket is perfect for layering over a plaid button-down and wool sweater. For winter, he also lives in a hat, like his Fisherman’s Rib Winter Beanie.


He rides his dirt bike basically until there’s snow on the ground (and sometimes after that) so warm layers are essential. And if we’re meeting with a client or on a project, he needs to look polished but still feel comfortable.

A light button down with a sweater keeps the outfit from looking and feeling too bulky. With a pair of lace up leather boots, like the Britton Hill Moc Toe Waterproof Boots, it’s basically an indestructible every day uniform.

When we’re hanging out on the weekend it’s definitely more laid back. We love to check out new restaurants and spots around the island or across the bridge. I really like this wool blend button down with jeans and leather boots.

The wool shirt is nice enough to wear if we’re going out to dinner with friends but also perfect for backyard football or walking through the woods. The quilted leather jacket pulls it all together and (according to Craig) is crazy warm, even with those chilly coastal winds.

I really like the waxed leather finish on this jacket because it has that look and feel of a jacket you’ve had for years. With a super warm insulated lining (at least 50% of which is made from recycled plastic bottles – pretty cool) this is an awesome gift idea for any of the guys on your list.


Jess Kirby is a fashion blogger from Rhode Island.  She’s wearing the Stratham Heights Chelsea Boots in these photos. Find her on Instagram .

See Jess Kirby’s style one of our warmest winter parkas and Whittemore boots