Right. You’ve gotten the basics of your outfits together and are looking to add some personal flair. Here’s some of the usual ways to do so, starting from the top.
Hats
I will confine my comments to hats for gentlemen, which are often a greater temptation on account of the lower cost for the otherwise uninitiated. Ladies, if you have the wherewithal to go out and get a fascinator or other similar formal hat you will probably have a sufficient grasp on the niceties of dress to warrant my reticence.
The Trilby and the Fedora
Chief among the temptations for gentlemen is the fedora and its close cousin the trilby. It is the unfortunate result of the proliferation of internet culture that the latter is often mistaken for the former.
In short, my recommendation is always to go for the former instead of the latter. The fedora is characterised by its wider brim compared to the trilby and hence flatters more facial shapes and silhouettes. It is an informal hat and thus not strictly appropriate for Black Lounge Suit (the second-most formal form of daywear) or evening dress (Black and especially not White Tie), but it is versatile otherwise and can be worn with more casual outfits. Be sure you are at least wearing a jacket.
The Bowler
Invented by Lock and Co. for a nobleman who needed sturdy hats for his gamekeepers, the bowler is another temptation given its associations with city gentlemen, civil servants, and other professional men.
It’s not a bad option, but the roundness of the crown means it can be unflattering to particularly round faces. Make sure you are buying a proper bowler, which should have a stiff even inflexible crown that holds its shape even when stood on (though I do not suggest you try this in a hat shop: just use your hands to get a feel for it).
The Homburg
The black Homburg hat with its significant central crease traces its lineage to German hunting hats. But it became in the 20th century a men’s dress hat, worn with lounge suits and Black Tie by such men as Anthony Eden and Winston Churchill.
Recommended (in black) for particularly formal daytime occasions and with Black Tie (take it off when you get there), and additionally in grey and other colours for daytime wear. I, personally, will be replacing my battered bowler once it gives up the ghost with a grey homburg.
The Top Hat
Another tempting choice for gentlemen owing to the familiarity of its silhouette. However, it is only really appropriate with White Tie and Morning Dress (morning dress tailcoat) so has limited utility. If you are contemplating this as a first or second hat, a homburg (above) might be a better choice).
Neckwear
If you choose to wear a bow-tie, a self-tied bow-tie is infinitely preferred to the pre-tied version not only because it demonstrates that you have put in the effort to learn to tie one, but because the asymmetry lends it a bit of verve.
Lord Peter Wimsey: This bowtie is a mess.
Dorothy L. Sayers, Gaudy Night, 1987 Television Adaptation
Bunter: Yes, too perfect. Quite like a made-up affair.
(He adjusts the tie)
Lord Peter Wimsey: Bunter, how’s that?
Bunter: Perfect. That is to say, slightly flawed. The mark of a true gentleman.
Cufflinks
Cufflinks come in many different shapes but are almost always (because they have to fit into a cuff) of similar sizes. The main varieties are metallic (including precious – gold, silver, platinum, and base – brass, stainless steel), jewelled, and enamelled.
A Club, College, or other ‘Institutional’ cufflink is almost always available to you and can be worn with propriety in most situations. It may even supply the subject of an ice-breaker and is therefore useful in that respect. A simple stainless steel, silver, or gold pattern will also be appropriate.
Pocket Watches
In an age when many functional vintage (second-hand) pocket watches are available on the internet for not much more than a lower-quality ‘new’ one, it is usually advisable, on the student budget, to scour the internet for deals before plumping for something new.
Old photos will show you many ways that pocket watches were attached to waistcoats. The option that gives the best appearance today is to use a chain with a t-bar that is inserted into one of the buttonholes of the waistcoat. The button is then also inserted into the buttonhole (relax, the extra bar doesn’t do either much harm) and the pocket watch is placed into one of the waistcoat pockets.
The pendant hanging from the t-bar is called a watch fob: an optional accessory that adds a bit of flair.
Socks
Black, grey, or navy in formal or semi-formal environments. Otherwise, wear what you like.
Italian outfitters to the ecclesiarchy Gammarelli produce some excellent socks in a variety of colours.
Sticks or Canes and Umbrellas
If you choose to wear a stick or cane (never ‘carry’) or carry an umbrella, ensure you are buying something understated to looking like too much of a tryhard.
A sturdy polished wooden cane with a crook handle and a brass collar is a good investment, as is a thin black cane with a silver top for evening occasions. Avoid anything that looks overlarge or plasticky or sold as a ‘pimp cane’. Vintage evening canes can often be had for a reasonable price.
With umbrellas, the classic choice is black, with a wooden handle and brass collar or cup.
You can’t go wrong with these choices, though if you are contemplating wearing or carrying either of these you will probably have enough of an idea of dress and outfits to make this advice unnecessary.
Mourning
If you are in mourning for a relative or other loved one, or wish to signify that you are adhering to a period of official mourning, this can be reflected in the way you dress.
Full mourning dress is black. Ladies wear all black. Gentlemen wear black jackets, trousers, and long ties with white shirts (hence our discouraging the choice of black long ties with sub fusc). Hats, if worn, are also black.
If you wish to wear other clothes, mourning can be signified with a mourning band, of some black ribbon or cloth material worn above the elbow on the left arm.
In academic dress, mourning is signified by the replacing of the tassel on top of the square cap with a rosette or tuft. If you wish to convert a standard mortarboard, tie a knot in the tassel which will both shorten it and give it when worn a tuft-like appearance.
