How To Dress Your Boyfriend: Formal Footwear

Dress your boyfriend (or hubby) in style this season with our picks for six different formal footwear styles for men. Oxfords, derbies and brogues—oh my!



The successfully stylish are those who transcend trends and interpret fashion in a manner so striking that it becomes inspirational. It’s not about having the most expensive suit or dress; it’s about how to create the perfect ensemble. Some people are gifted with an uncanny knack for pulling off a prêt-pour-le-catwalk look, but others are not so blessed.

Delving into a realm of the unknown can be, well, nauseating for some (and terrifying for others). But if you look at style as a sort of game, it becomes fun. Be bold. Be daring. Be who you want to be. That is the most marvelous thing about fashion, it is truly unique from one wearer to the next.



Photos from Ermenegildo Zegna runway show by Anthea Simms


This week, How To Dress Your Boyfriend is talking shoes. With a plethora of options, varying in style and design, anyone could easily be put off by the shoe department. But, follow these next few weeks of instruction and you’ll be on the way to dressing your man’s feet (in style!) in no time.

Men’s footwear is a rather vast topic, so HTDYB will break it into three categories: formalwear, shoes for the weekend and office appropriate styles. This week—no rhetoric, just direction and picks—I dissect formalwear.


Read on, fellow stylewashers!



The Derby, quite the opposite of an Oxford with its exposed eyelets, can blur lines between casual and formal. Paired with black or indigo denim and a crisp white shirt he’ll be ready for any occasion, whether dinner and cocktails or a charity gala.


Tiger of Sweden buffed calf leather Vince derbys, $230,



Identified by smooth lacing and hidden eyelets, the Oxford redefined mens footwear when it was introduced centuries ago. A nice pair of Oxford shoes (which could even be brogues) will complete his tailored suit, or dress up those jeans he just can’t take off.


Lanvin burnished leather oxford shoes, $930,

Drivers & Loafers

In recent years the driving shoe and loafers might have tiptoed their way into the world of formalwear, but without due thought it is easy to misstep your way into the land of too casual. Proceed with caution.


Bally Wabler leather driver shoe, $436,


The brogue shoe was originally developed in the lowlands of Ireland and Scotland to offer working class men a shoe that drained of water when stepping out of the bog. Today, it has shed its plebeian roots to become a statement-making design feature.


Insolito Terra Charlesworth shoe, $250,

Black Tie

Patent leather shoes are the traditional pairing for tuxedos. Though some men might dare try on a matte option, coerce him into selecting patent. No man wants to be the odd one out at a black tie function.


Ted Baker Billay shoes, $185,


The double monk strap is a style that attracts the eye no matter what. Best used as a statement shoe with a grey or navy suit, the monk can also be worn with indigo denim or pleated trousers to perfect the garden party look.


Moncler Gamme Bleu, $847,