San Fran Day One: Leather Jackets and Boots

On our Thanksgiving break, we were fortunate enough to go to San Francisco.  Obviously, we took the opportunity to layer up and do some amazing outfits.  Here’s what we wore on our first day.

Street Leather on Tim

The key to pulling off leather is keeping things nice and simple.


Here, under the leather Tim is wearing a simple checked red flannel shirt and dark blue skinny jeans.  It’s always nice to cuff jeans when you wear boots, since boots tend to ride high on the leg.  Just a note, his desert boots are the chukka style from Clark’s, a brand that has its roots in the British Military.  He even color coordinated by wearing red camp socks.


What makes Tim’s leather jacket unique is the fact that it has a fleece lining and hood.  This combination ensures that the wearer will be warm.  The jacket’s hood also adds a streetwear look to an overall “hipster” or “lumberjack” look.  This is Tim’s style; he isn’t afraid to mix different styles.   This is also an example of how one piece of clothing can change the whole look of an outfit.

Leather jacket from OBEY, Jeans from PacSun, Chukka Desert Boots from Clark’s USA,

Red Flannel shirt from Urban Outfitters 

Modern Fighter Pilot on Ethan 

Personally, I have always been a fan of vintage items and I love to take one vintage piece and use it with other modern clothes.  There is nothing that screams cool to me than a leather fighter pilot jacket from the 1940’s.  In fact, that’s when leather jackets first came about.  Planes back then didn’t have much insulation, so pilots wore one of the warmest materials:  leather.  Eventually in the late 40’s as men came back from the war, more people wanted to wear them, so they started mass producing leather jackets in the same fighter style.   This also came through from leather motorcyclist jackets from the 30s and 40s.   I was lucky enough to own and wear the true vintage 1940’s leather jacket in this post.


Even though this is legit vintage leather, it has aged to be soft and versatile while being warm.  Even though I have the jacket, I layered with the same green sweater from before.  Under the green sweater is one of my favourite shirts: blue denim shirt with brown buttons.  Like I said before, blue and brown go together really well.


The combination of leather, denim, and wool gives texture to a warm outfit like this one. For pants, I wore slim fit black chinos with a great pair of normal work boots.  Like Tim, I matched my socks to my outfit by wearing green camp socks.

Vintage Leather jacket from the 1940’s, Denim shirt from H&M, Green Merino Wool V-Neck sweater from H&M

Black Chinos from PacSun, Green Socks from TopMan, Work Boots form Nordstrom

So if you’re looking for something that everyone fashion conscious person should own, this is it.  There are many different styles of leather jackets out there today, so there is no doubt that you’ll find something you like.  Just make sure it fits!  Boots are also a classic staple of menswear.  Start getting these items and create a great winter outfit!  There’s only a few weeks left of it!


Ethan W.

Street x Sprezza

Photography by Tim and Ethan


Ethan on left, Tim on right 

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