Certain things from my '80s childhood I simply can’t shake. Immediate-to-mind examples include a fixation with owning lots of watches (read Swatch conditioning), my affinity for baggy, off-the-shoulder sweatshirts (my Jennifer Beals crush began) and preppy core essentials, like Top-Siders.

Created in 1935, the Authentic Original Sperry Top-Sider is the blueprint for the American boat shoe and the cornerstone of classic nautical style. It also became the quintessential shoe for the preppies-turned-yuppies nationwide.

I think it’s time to bring these back into your wardrobe. Perhaps it’s the classic pair (pictured above on left) or a newer version like these shiny crocodile kicks, which offer a more dressy variation and work into fall. Both are from Sperry and run about $80.
Sebago offers a more refined version of the boat shoe. However, they’ve kept the signature lacing and reverse stitching. I particularly like this bone and soft brown color combination, although they offer several others in bolder combinations. They’ll cost you about $84.

I can always count on J. Crew to turn out a comfy, stylish, slightly tweaked version of what is hot. I have considered buying these particular shoes, which are technically driving moccasins, for months now. With fall’s arrival, I should tuck my flip-flops back in the closet and opt for something more substantial, and these may do just the trick.

With a tumbled-leather upper, heavy stitching and a shiny brass ring, these ground the most conservative of outfits. I even like the graduated rubber sole, which means you get comfort and a little extra height, which is always good. I chose green because my policy is "if it matches nothing, it matches everything," and the rest of my outfit would be neutral- and light-colored. These run $128.

If resistant, your entire outfit doesn’t have to scream preppy. Rather, paired with khaki wide legs or jeans and a t-shirt, Top-Siders can be your subtle wink back at the '80s.