A Prohibition Party Outfit

I attended two parties on New Year’s Eve; both themed. The first was a Prohibition theme.

This called for a 1920s-inspired outfit, which is something I’ve never done before. It was a fun challenge!

I knew I wanted to wear an outfit with high waisted pleated trousers, shirt with spearpoint collar, braces, necktie and a flat peaked cap (I’m yet to find a brimmed hat that I don’t look foolish in).

How It Came Together:

Components from Home

With a couple of weeks in advance, I had time to shop around for some authentic looks.

Things I didn’t need to shop around for were trousers, possibly a jacket and a flat peak cap. I used some old no-name vintage cotton pleated pants (with brace buttons freshly sewn in) in navy, and a Dents flat cap in mid grey flannel.

I didn’t decide on a tie at this point, though I had several that could have fit the bill. For a pocket square I decided on my John Henric white linen with navy trim to echo the pants: this would also influence the tie choice to something with navy as a secondary colour.

The rest needed to be acquired. I didn’t own a spearpoint shirt, or a pair of braces. I decided to try and find a pair of spectator or buck shoes if possible also, though didn’t hold much hope in that.

Shirt Purchase

I struck gold on a Sunday afternoon when I visited the vintage store A Star is Worn in Norwood, and happened across this cool linen-cotton spearpoint shirt in yellow with stripes.

I knew I had to have it for the outfit.


At this point, all that was left was to accessorise and decide on a jacket. I needed to find some braces and choose a necktie.

For the braces, I raided my friend Blake‘s (the man behind Blakesby Hats) rather large wardrobe-in-storage. We found a suitable pair of braces in a burgundy with yellow stripe. He also offloaded an old three button linen jacket which was a bit more vintage styled than the Corneliani one I usually wear, so I opted for that in the Prohibition outfit. It’s really a little too tight to be worn buttoned, but wears fine when open.

A good match for the shirt, too.

For the tie, I went with a striped piece by Zegna. It fit the 1920s bill with the stripes and small motifs. Best of all, it was unlined which allowed me to get a smaller knot.


As expected, I didn’t manage to acquire a pair of spectators or bucks. So, I settled on an old pair of country brogues by Geoffrey Beene that I often wear with more casual looks. You can see the shoes in question below.

That’s all for today!

Stay tuned for the second NYE outfit, which was for a Cuban themed party.

Did you attend a themed party for NYE? If so, how did you dress?

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3 thoughts on “A Prohibition Party Outfit

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