I’ve been meaning to go to SF (and the Bay Area) and shop around for a long time. The last time I went was two years ago when Tim and I stumbled upon Haight Street and its awesome vintage stores. I planned to go for my 21st birthday in July, but circumstances arose that only allowed us to go during this past September Weekend! Spencer, Jeremiah and I (the Spring 2016 Dapper Day crew) were only able to spend two nights/one day in the Area but it was definitely a lot of fun, especially since we were able to dress up and walk around!
1950’s/Workwear Vibes on Spencer
We left LA on Friday afternoon and didn’t get to Berkeley around 7 or 8. Since we didn’t have much planned except for dinner and hanging out with our friend Jay (who has been featured here before), we didn’t go too crazy. This is Spencer’s fantastic example of casual style, with some 1950’s and workwear vibes. He has the cuffed jeans and boots down, but instead of a chambray shirt and chore coat (which is what the natural combo would be), Spencer went with a rayon 1950’s shirt and a perfect compliment to his true vintage sartorial style. Great outfit for dinner in the town.
1950’s Rayon Ricky Jacket, 1950’s rayon shirt, Levi 501s, Chippewa Boots
Vintage and Sprezz on Ethan
Thanks to Ethan Newton from Bryceland’s Co, I’ve been really intrigued about combining vintage and modern clothes in a new way. While I love doing my spearpoint shirts and vintage ties with my chinos and sportcoats, Mr. Newton tends to add a bit of workwear/1950’s chic with this sartorial pieces. Stuff like this and this was a real inspiration for me.
This outfit is one of my first real forays into a true combination of vintage and “tailored casual”. I wear a reproduction 1940’s wool jacket, a custom shirt, grey chinos, and tassel loafers. It’s pretty much a modern interpretation of the short jackets found here. Normally I’d go sockless with my loafers, but since NorCal is colder than LA, I kept my socks on.
This picture can really show the textures and pattern matching in the outfit. The custom shirt is a gorgeous shade of blue, with a diamond print. In my commission, I asked for a 3.5″ spearpoint collar and two breast pockets; it really calls to mind vintage 1930’s workshirts and RRL shirts. Workwear vibes are extremely aparent here.
The micro patterned workshirt mixes well with the bold two-tone plaid jacket, while the neutral blues, browns, and greys anchor the outfit. I wore this for dinner with Jay and the guys in Berkeley, so the jacket definitely kept me warm as we walked around town!
repro 1940’s Jacket, custom shirt from Natty Shirts, BR Aiden Chinos, AE loafers
Nice and Simple on Jeremiah
Jeremiah doesn’t usually dress up unless its Dapper Day. Even though he isn’t in a tailored clothing, he really rocks the dressed down look. For Saturday, the day we spent shopping and walking around, he really went for comfort. Jeremiah wears a simple black crew neck sweater, some slim denim, and high top Converse. Not flashy at all, but I really dig the neutral basics and the fact that everything fits very well. Much better than the countless tourists in the area.
1930’s Sportswear on Spencer
Spencer decided to give us the true vintage version of the satorial polo shirt. He wears a reproduction 1930s polo shirt from SJC along with an amazing 1930’s windowpane sportcoat; he pairs a pair of RRL linen trousers with his ensemble. While the look is definitely vintage, it’s not hard to recall that many guys wear similar outfits at Pitti Uomo, one of the biggest #menswear gatherings of the year. Instead of going for an italian look, Spencer looks like what I imagine casual style looked like in San Francisco in the 1930’s.
If you’re curious, casual style back in the Golden Era was referred to as “sportswear”. It was not the same as what we consider athletic wear today.
Going Ivy on Ethan
I keep getting outfit inspiration from a variety of places! This one comes right to us from the 1960’s, the age of ivy. I had just finished Alfred Hitchcock’s film North by Northwest, where the main character (played by Cary Grant) has an impeccable wardrobe. In the climax of the film, he swaps his Saville Row tailored suit for a simple pair of pleated trousers, an OCBD, and penny loafers. The use of the OCBD and penny loafers with white socks really signify the “ivy” influence for fashion in that period of time. I normally look at the 1930’s for my outfits, but something about the look intrigued me.
While the OCBD works well with the high waisted, pleated (but slim) trousers, I knew that something was missing. I added a wool/cashmere jacket to finish off the look as a layering piece! The patch pockets make it casual and easy for me to carry my wallet and phone without bulging my pant pockets. Bulging pockets on pleated pants doesn’t look good. The brow-line shades really make this a throwback outfit.
Not many places make a good OCBD with enough collar to roll like back in the 1960s. Instead of paying a lot of money at Kamakura shirts or Brooks Brothers (who make fantastic shirts), I asked my shirtmaker to make one based on vintage measurements. The result was an amazing, high quality shirt that rolls like any true ivy shirt. Can’t be ivy or trad without a great collar roll!
I don’t always wear white socks, but they’re needed to make a real ivy look. It’s not recommended for everyone, especially since white socks are most commonly associated with people who dress poorly. Most of the time, a normal dress sock or even going sockless is preferred. However, if you aren’t wearing atheltic tube socks and you have a pair of sharp shoes and contrasting trousers, it can look very cool especially if you lean toward a vintage style yourself. Just look at this 1960s gent or this graduating class!
Wool/Cashmere suit jacket from Suit Supply, Custom OCBD,
thrifted pleated pants (tailored), AE penny loafers
Our first day really consisted of driving, so there really isn’t much to see. It wasn’t until we got to Berkeley when we were able to relax and actually have fun! We met up at Jay’s place, where I was able to give him some clothes that I don’t really wear anymore.
I gave Jay the suit I wore from when I went to the Getty. It’s a nice vintage three piece from Ralph Lauren that I just don’t wear anymore due to the cut and very low buttoning stance. Jay wasn’t complaining; I’m practically subsidizing his future corporate attire!
After catching up with Jay, the gang went to Angeline’s Louisiana Kitchen. We each ordered their fried chicken, which came with a sweet potato (or yam?) mash and string beans. We even ordered a bowl of mac and cheese for the table.
Saturday was spent mostly at Haight and Ashbury, checking out vintage stores. We went to Decades of Fashion and Held Over to see what we could find! Unfortunately, there was barely anything in my size, but I did get a nice 1940’s suit for cheap! Be prepared to see that at the next Dapper Day!
For lunch, we ate at Burger Urge. I had a patty melt while my friends both ate burgers.
We finished off our Saturday by heading to Market Street where I was able to check out the Levi’s store and see the LVC denim that Spencer had been raving about. I tried on the 1955s, the 1966s, and the 1933s ; each are selvedge and “shrink to fit”. I didn’t buy any, but I was definitely considering the 1933’s for a future purchase! Here are the pictures in order as previously listed. Let me know what you think!
The guys and I then had dinner at the Sears Fine Food restaurant, where I had a New York Steak.
We left Sunday, but not before taking the time to check out my friend Sam Simmons in Oakland! He owns the vintage shop Over Attired, where he sells men and women’s clothing from the 1920s-1960s. I was delighted to see him in a colorful, casual vintage outfit!
Most of the money was spent on food for the trip, but I did manage to cop some sweet stuff! The first item I got was a late 1940’s DB suit in a dark grey with subtle brown/red windowpane. The pants have dropped loops and pleats! I’m hoping to wear this for the next Dapper Day in November; I don’t need to tailor anything of it, so it should be good to go!
The second piece I got was from Over Attired, Sam Simmons’ store! This is a fantastic varsity jacket from the 1950s-60s, which sits pretty high (perfect for high-waisted pants) and sports a fantastic logo and lettering on the back! I’ll probably work it into more vintage casual or ivy looks in the future! Check out his website or his etsy store!
I hope you guys enjoyed this post! I’m sorry I didn’t really get to cover any of the typical SF areas or even any museums, but I really did just want to go for the clothes and friends! I’ll be honest; things haven’t been so great lately, but going on this trip and being allowed to indulge myself in my hobbies, hang out with my closest friends, and eating some freakin’ great food definitely helped!
Let me know what you guys think! Do you like the ivy look? What do you think of the more rugged “tailored casual” attire? And please help me decide which jeans (if any) to get! Leave a comment below!
Always a pleasure,
Street x Sprezza
Photography by Ethan W. and Spencer O.