Gucci Leather Lace-Up Boot: Don’t think about tucking in these bad boys, they weren’t meant for it. Try accessorizing your suit to match the laces, as it’s always all about the little details to make your look pop. Available at BlueFly for $607.50.


Cole Haan Air Rhone Tall Boot: Intimidating to look at, but sturdy with a bit of a platform; perfect if you want to be the taller of your pair. With this color, stray away from blacks and navys, instead opt for a light khaki—it’ll make you stand out. Good accessory tip? A patterned pocket square with yellow accents. Trust me. Available at Cole Haan for $248.


Frye ‘Thurman’ Boot: Now we’re talking. A dark chocolate brown boot that has comfort, a rugged edge, and is prime for tucking. When you see this boot, I’d say go for a darker khaki or navy and pair with a nice tortoise shell lens. Available at Nordstrom for $358.

Palladium ‘Baggy’ Patent Leather Boot: If you’re doing an outdoor wedding with urban flare, these are the perfect boots to bring flavor to the aisle. Available at Nordstrom for $125.


Calvin Klein Jeans Billy Buckle Boot: For the prepster who is given limited options, look no further. Calvin Klein’s Billy Buckle Boot is sure to give you that prissy, clean-cut vibe you’re looking for. Plus, if they get dirty, they’re very easy to clean! Available at Calvin Klein for $149.

Levi’s Wild Boots: These boots are perfect for a texturized look. Charcoal or navy, tucking your suit into these with a fitted tartan shirt adds an instant eye-catching rustic allure. Ideal for the fall or winter! Available at Macy’s for $89.99 (regular price $115).

By Jonathan Bender