Leather Ankle Boots: Trendy, Stylish and Practical


One trend that has been on the steady rise this fall is the resurgence of stylish, leather ankle boots that can be worn either dressed up or casually.

The leather boot is a great item because it gives men another option between the sometimes-limited choice of either loafers or regular lace-ups. They thus add an extra flair to an outfit that says the wearer tasks risks and is confident in his style decisions.

For a dressed up look, they can easily be used as a substitute for either loafers or oxfords, depending on the suit. In general, dress boots tend to be on the side of modernity and therefore look better with equally modern suits; the slim-cut, two button styles. This pair from John Varvatos demonstrates that simplicity and restraint are the highest qualities in men’s shoes.

An easy way to wear boots more casually is to choose a brown pair. These are much more easily matched with varying hues of jeans, meaning you get more versatility and wearability. The exact same pair of John Varvatos boots in brown shows the remarkable difference that color can have on the ‘formalness’ of a shoe. Here, the handsome, marbled wood appearance makes them acceptable wear for an everyday look that would not be appropriate in black.

My favorite look is a pair of dark skinny jeans with boots and a waistcoat, which I witnessed to be a very popular look among young, fashionable Londoners last spring. It’s clearly not a look that is easily pulled off by many; a certain je ne sais quoi, rocker-chic is necessary trait for the wearer.

When buying a pair of boots, one thing to make absolutely sure of is that the end be pointed rather than round. While, a rounded pair will make you look old and patently uncool, a narrow point indicates self-assuredness as well as being generally much more fashion forward, if that’s what you are pursuing. Another thing to avoid are ‘hybrid’ boots that have laces but still try to masquerade as a dress boot, or even worse, turn into a ‘combat boot’. Pictured pair from Costume National is a heinous and glaring example of what can happen when the two very separate entities are combined: You end up looking like a combination of Hermione Granger and a suburban, gothic mallrat.



  1. I feel like the critique of those Costume National boots is a bit unfair. While it may not be YOUR aesthetic, they certainly are provocative and would be perfect for some people’s sense of style. Although I do enjoy reading Men’s Flair, I don’t really appreciate this sort of close-minded approach to fashion.

    Just look at people like Carol Christian Poell, Rick Owens, Hedi Slimane, Yohji Yamamoto, Rei Kawakubo, many of the Antwerp Six have built their careers on highly forward, if not necessarily mainstream, fashions that have earned them praise from plenty of critics.

  2. Thanks Marcus for your comment.

    The one thing I always ask of writers at Men’s Flair is to be brutally honest in expressing their opinion. It may not be liked by many, but I would always chose honesty over likability.

    That way your own honest comment is also more appreciated than if you had just written “I like your article.”

  3. Sue Ellyn says:

    In my opinion, Drew’s critique of the Costume National boots was completely justified. In order to make it in the cut-throat fashion world of today, one must define their style and not be afraid to point out what one dislikes. Drew was merely giving an example of one style he is not partial to, and he has good reason these boots are atrocious. People in high fashion should not be wearing such gross looking shoes, the only people should be wearing them are those in the army.