The London Lounge

I assume a homburg would be ideal and I guess a (black) bowler would be OK. Would a charcoal trilby be too informal? How about a topper?

A nice soft black Homburg. Top Hat is for White Tie. Bowler these days is just for the Hunt, if your elected representatives allow you this indulgence.

Black homburg. Or a charcoal homburg.

A trilby or fedora is a bit too informal.

Although a silk top hat looks great in photos of ages past, it is costume. Same for a bowler hat.

I wear a stroller whenever the occasion permits. Although I do not wear hats at such times, I admire them on others. The charcoal homburg would be perfect, especially with a dark overcoat.

Simon A wrote:ATop Hat is for White Tie.

Surely a topper is also for mornign dress. I thought a stroller was to morning dress what a DJ is to white tie?

Mark Seitelman wrote:Although a silk top hat looks great in photos of ages past, it is costume. Same for a bowler hat.

I would hesitate to say that, in London, bowlers and toppers are 'costume'; at least any more than white tie, morning dress and strollers are.

I guess I stated the question wrongly: when strollers were routinely worn, were they worn only with homburgs or was other headgear commonly associated with it?

A couple AA "arguments from authority":
http://4.bp.blogspot.com/_Wbd-uMYmb_4/T ... roller.jpg
http://4.bp.blogspot.com/-7FaV57l6_YA/T ... epherd.jpg

I think a homburg is 'most correct', but even more so than black tie, the stroller or Stresseman is a fairly un-codified style of dress that gives some leeway. I'm pretty certain that it was also frequently worn with bowler hats, at the peak of the bowler's popularity. Searching the web, this article claims that the bowler and Eden were specifically stroller hats: http://www.gentlemansgazette.com/strese ... z2nqUiYH5a.

Backing up that contention, Leon Drexler markets what looks to me like an Anthony Eden hat (essentially just a toned-down homburg) specifically as a "Stroller hat": http://www.leondrexler.com/New_Leon_Dre ... oller.html. And I'm sure other homburg variants like the Lord's hat were and are appropriate as well.

Thanks for the very useful response and Merry Christmas.

A slightly different answer from me, I break the rules a little bit with headwear with regards to both strollers (or black lounge) and black tie. Whilst the homburg is the most correct option, I go with a black wool flat cap (one of the stiff moulded wool type). It is much more informal, but in this day and age I end up looking more stylish than most of the guys around me (plus, the rest of the outfit is more or less spot on, so the small items of outerwear and where I introduce my grosser variations).