From beautiful bowlers to tip-top top-hats, from fantastic fedoras to perfect pork pies- the range of vintage hat styles on offer to men means there’s no way the excuse ‘hats don’t suit me’ can ever be used. There’s a hat style for all you vintage gents out there, it’s just about finding the one that suits you. George Walker talks through the best hat styles for Sixties-inspired Madmen to Dickensian Artful Dodgers.

Hats used to be a gentleman’s fashion staple. In the Victorian era gents would don their top-hats on carriages; in Fifties New York streams of fedora-wearing businessmen would flood the steps of Grand Central Station; over in London bankers would march across London Bridge in sturdy bowler hats.

Recent films and TV programmes like Madmen, Revolutionary Road and Far From Heaven show how vintage headwear can really pull together an outfit. Both smart and striking, hats offer a step back into the heritage of men’s tailoring.

Although today most of us still wear hats to keep the sun off our necks or the chill off our ears, it seems beanies and more casual styles have taken over from smarter and more elegant designs.

I asked Lucy Davies, owner of new retro-style hats supplier Mad Hatters, if she thought vintage style headwear will always be fashionable. She said:  “Yes. I definitely think the fedora and the bowler hat, yes, definitely. I think hats go in stages,  in waves, like other things taking over like the pork pie hat- that’s very popular at the moment.”

Although there can be no doubt that a man looks dapper in a smart fedora or bowler hat, it’s also true that we just don’t get to see these styles as much anymore. Take the following lines of poet Billy Collins’ ode to hats in ‘Death of the Hat’ for example:


Once every man wore a hat.

In the ashen newsreels,
the avenues of cities
are broad rivers flowing with hats.

The ballparks swelled
with thousands of strawhats,
brims and bands,
rows of men smoking
and cheering in shirtsleeves.

Hats were the law.
They went without saying.
You noticed a man without a hat in a crowd.

‘No more!’ I say- now is the time to put your thinking cap on and choose that perfect vintage hat to bring a bit of gentlemanly style to the streets of your town.

We adore a fedoraFar from heaven denis haysbert

What is it?

-A felt hat that is creased down the crown and pinched at the front. They have a full brim and often have a band in a satin material. From around the Twenties fedora hats became a middle-class business man’s wardrobe staple.

Why we love it

-The fedora just oozes style. Recently it’s been worn in some of the most stylish films and tv shows set in the past, including Leonardo DiCaprio in Revolutionary Road and all the dapper guys in TV series Madmen. It’s also been worn by vintage icons such as Humphrey Bogart in Casablanca and Morgan Conway in the 1945 Dick Tracy film.

Because of the pliable and yet smart shape of the fedora, it’s a great hat for smartening up an informal outfit with a bit of vintage style. In Todd Haynes’ marvellous film Far from Heaven (2002) Dennis Quaid and Dennis Haysbert (pictured) both wore fedoras in Haynes’ vision of Fifties America.



Artful dodgerDon some Dickensian headwear

What is it?

-Here we’re talking about the top-hat, probably the most formal and hardest to wear hat. The top hat varies in height, from extravagant towering numbers to the shorter, ‘Wellington’ style top hat with pinched in sides. Originally made from beaver fur, top hats were most commonly made from hatters plush (a soft and yet durable silk weave.)

Why we love it

– Initially the top hat may seem a bit of a daunting prospect, but there are many different styles of to choose from. Lucy Davies of Mad Hatters said the resurgence in top-hat popularity is “very influenced by the Alice in Wonderland thing and you actually get a lot of people who want to wear them to the cinema, and there’s lots of madhatter’s tea parties going on.”

A particular favourite of mine is the beaten-up Artful Dodger-style top hat as shown in this picture of the original cinematic Dodger in Oliver! (1968) Admittedly it isn’t an easy look to pull off, but paired with a wool overcoat, slightly shabby waistcoat and a loosely tied cravat, a top hat can look really striking. Go on, make a cheeky nod to Dickensian style with a top hat- I dare you!


Bowl us over with a bowlerCharlie-Chaplin_l

What is it?

-Everyone knows the bowler hat (or Derby hat as it’s known in the US.) This hard, round felt hat with a short brim was originally made to protect horse riders’ heads from tree branches. The bowler is a smart no-nonsense piece of headwear. Worn by icons such as Charlie Chaplin, Laurel and Hardy and- erm- Mr Benn, the bowler is a hat style full of cultural history.

Why we love it

-The bowler is a great choice for any vintage gent wanting to wear an accessory that smartens up his outfit without making it too business-like. In fact, the history of the bowler as a hat originally developed for horse riding points towards the fact that this is a hat style that can look good either with a smart work suit or a more rock/ beatnik style of outfit.




Style Tip No.1: Mad for hats? Try Mad hatters.Madhatters

Madhattters Dickensian

One of my favourite shops in Brighton is Mad hatters. It’s an emporium of delectable headwear for both vintage-loving guys and gals. Although the shop sells only new hats, there is a strong focus on vintage styles. Fedoras and top hats line the walls of the shop in a range of classic and more unusual colours.


If you fancy a suave top-hat (pictured) or stylish fedora, but you can’t make it to Brighton, don’t worry. Mad hatters has a number of stockists including over 20 John Lewis department stores. You can also order by telephoning the shop (details on the website.)


Style Tip No.2: Vintage findsBowler find

Of course as vintage lovers, there’s no better hat than a real vintage hat. Classic styles such as the bowler have been made across the decades, but this smart vintage bowler  is full of history, complete with its original ‘Leilers of Neath’ packaging.

Vintage hats do tend to have signs of wearing, but this can add to the slightly dishevelled bohemian look that many of us guys are after. If you want to keep things smart, however, why not just add a new silk band to a hat, perhaps in a more striking colour to add a touch of modernity?



Style Tip No.3: The American hat giantBailey Gangster

The Bailey hat company was established in 1922 by George S. Bailey. As the company grew, Bailey began to make hats for the biggest stars of the era including Humphrey Bogart, Cary Grant and Bing Crosby.

Today the company is split into two divisions; one being the Hollywood line of vintage-inspired styles and the other being the Western range which focuses on western cowboy hats and such like. I have a Bailey fedora myself, but this grey felt fedora complete with feather is certainly making me want to add to my hat collection…




3 Responses

  1. Paul

    Great post, it’s a real shame that you just don’t see them worn very much these days.

  2. Jared Resnick

    My spouse and i was not aware of quite a few the data that you just talked about i actually wish to just express gratitude

  3. Anastasia

    Thanks for the great article! I was especially interested in the info regarding the Bailey hat company. American made products are difficult to find so I will definitely keep the name handy when I next purchase a hat for my spouse.