Cuban heels and Beatle boots are making a strong comeback. That look from the late 50's and early 60's has proven itself to have staying power, and today's fashionistas are strongly in favor of both looks. Some styles just come and go, but these two boot styles have proven themselves to be both Retro/Classic and up-to-date.
Cuban heels, a modification of a Flamenco dancer's boot, have that edgy look that is now a mainstay of casual wear. The Beatle boot, which is based on the Chelsea boot, with a stitched seam running from the ankle to the toe, is showing a steady surge in popularity. Both styles have the advantage of Time. Over time, they have become part of the fashion World, both as easily recognizable styles in and of themselves, and as proven fashion accents that work. Today's versions of these styles now feature deluxe leathers and bespoke construction, if you know where to go to get the best examples.
One of the most appealing aspects of these styles is their flexibility, in terms of apparel choices. They go with dress pants and blue jeans. They can appear on the Red Carpet and on the dance floor. Best of all, they make a strong, positive statement about the wearer's fashion sense. The guy who shows up in these boots radiates confidence and fashion sense.
The choice for you to make is which style works best for a given look. Remember, what may be best for a night out on the town may be different from a day in the city. Most importantly, as you continue to consider what's best for you, it may be best for you to have both styles, and adapt them to the venue you will be attending.