Answering Your Questions on Vintage Style

I'm answering patreon questions about vintage style, hats and classic casual
items. Learn how to build you retro style one piece at a time.
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What hat gets the most wear in your wardrobe? What hat would be worth a splurge?
Well there at a lot of hats in classic dress and almost as many in my own personal wardrobe. I’m not sure how may I have but the largest group is straw boaters. When is comes to a signature hat that is unfailing in it’s ability to complete an outfit the straw boater literally takes the cake! I love a boater and though I would love to wear it year round hat just like clothes have seasons. Boaters and all straw hats are typically worn in the spring and summer which begs the the questions, what is in my winter hat wardrobe? For that I would need to go with the fedora. Now a fedora has become a catch all name for any hat that has a snap of the brim and a teardrop crown but not all these hats are the same and not all will look the same. Just like any item its all about how you style it. The creases, dents, bends and tile of the hat can make all the difference.
Theres a hat I've seen you wear that looks like an oversized, newsboy cap. What kind of hat is that and how do you style it with your wardrobe?
Great question The newsboy cap is a type of flat cap. Flat caps, which are called everything from Cheese cutter in New Zealand to a Driving cap in the United States are a type of headwear that are quite old and are said to date back to the 14th century in parts of the Northern UK like Leeds and Manchester and parts of Scotland. It’s often associated with country living and working class people. It’s designs differ from the newsboy a bit in that flat caps tend to have a more oval top and are completed without the button on the top. The newsboy cap is often an 6 or 8 panel cap. The bigger and blousier versions of the hat are call applejacks and the even bigger a big apple. Since its a decidedly casual hat, I either use it to match something that is possibly a bit casual or to tone down a item thats more formal. For instance when wearing plus fours, I really lean on the newsboy or applejack a lot because since the 1920s plus fours have be designated at sports wear. So I like to incorporate them into looks that are on the less formal end of the spectrum. Also practically, I wear these types of caps when it’s windy or it’s cold especially my wool ones. Speaking of casual items here’s this
Could you do a quick overview of casual vintage clothing, preferably from the 1930s to 1960s- like outfits that aren't full suits.
When looking at vintage casual wear a few key is comfortable separates. Items like Sweaters, unstructured Jackets and wide leg denim and trouser are some of the staple for casual wardrobe. For sweaters I suggest looks for collegiate and letterman sweaters as well as shawl collar they can soft and cozy but have details that allow them to work in so many occasions. Of course sweater vests are making a “come back” in pop culture, news flash they never left. But pull over and bottom up sweater vests can be a great way to adda vintage aesthetic. You can wear a button down, polo or long sleeve polo under all of these.
When it comes to unstructured jackets my go to is a 49ers Pendleton jacket. They are super comfy and but have all the details that make them seem dressed up. There are characterized by wide point lapels, three to four patch pockets and bottoms down the front and cuffs (sometime leather). Hot take - If you have buttons on something these days you level up the dressiness of it. Also get these Pendleton jackets on eBay or etsy. don’t buy them new until you read up to of the conversations around Pendleton and cultural appropriation. Other similar jackets exist from Eddie Bauer and Woolrich
Finally I would suggest finding some wide leg denim or trousers. They can wool, corduroy, or even denim. But the wider they are they more vintage they will look. For me pleats are always a plus but some without can work.