What to Wear with Sperry’s Annapolis Brown Leather Boots

Boots are a must have for surviving Fall and Winter. Sneakers and dress shoes are geat. But they won’t take on the elements as well as a pair of boots. This season I partnered with Sperry to show you how to style some of their preppy staples. You can read my previous posts here and here. In this post, I’ll be sharing how to wear Sperry’s Annapolis brown leather boots.

The Annapolis boot is the perfect shoe for everyday wear. It seems like I’m never home. So if you’re like me it’s important to have a pair of shoes that are ready for any occasion. Not only is style important, but comfort is key. The Annapolis boot features a footbed that molds to your foot. So you’ll look and feel good all day long.

These boots are meant to be worn to the office. But the chunky sole and vintage look gives the boot more a versatile and casual feel. If you’ve got any events coming up with a semi-casual dress code, these should be your number one choice.

So what do you wear with a boot that looks semi-casual? Keeping up with the theme of redefining preppy style, I wanted to share a look that was sleek but still casual. This season I’ve really been into layering neutral colors and tones. So I’ve paired my brown leather boots with a turtleneck and dress pants. I finished off the look with a camel topcoat. What I love about this look is that it’s polished but not too stuffy. 

The only downside of boots is that they tend to be expensive. The Annapolis boot is well under $200. So it’s a super affordable option to help you survive the cold weather season. Click any of the photos below to shop!

Shop My Brown Leather Boots Outfit for Men

Sperry Annapolis Boot | Tom Ford Clint Aviator Sunglasses | Express Wool-Blend Topcoat | Express Wool-Blend Turtleneck | Express Extra Slim Dress Pants