Spring poses a bit of a sartorial conundrum. It’s not quite warm just yet, but it doesn’t feel like winter, either. Yet sometimes Mother Nature messes with us by staging a sudden mid-March snowstorm, injecting the forecast with a balmy summer teaser, or drenching the city in a flood of rain. These rollercoaster weather habits may be mildly entertaining, but they also make it tough to slip into the appropriate pair of shoes in the morning. Is it a boot day or a canvas sneaker day? We’ve rounded up six smart, styled options that are destined to keep you comfortable no matter what the conditions.

Low-Profile Boots

Giancarlo Weatherproof Chelsea Boots

It’s safe to say you probably won’t require the hardy, thick, heavily insulated boots you reserve for winter wear. You might, however, wish you had a good pair of off-season boots to tackle the occasional bout of wet spring weather. Turn your attention to low-profile silhouettes that extend no further than ankle high. The effect is more dressy than utilitarian, especially when you select a pair that fits into both professional and casual wardrobes with ease. Aquatalia has the answer in their Giancarlo Weatherproof Chelsea Boots ($550), which capture the spirit of timeless sophistication in a sleek, handsome, and practical configuration that’s worlds apart from the rugged shoes you sport during winter. They earn bonus points for wearing just as well with a suit as with jeans and a sports coat.

Sturdy Chukka Boots

Frye Bowery Leather Chukka Boots

If there’s no sign of rain or snow in the forecast but you can’t imagine heading outside in flip flops, sneakers, or sandals, step into a pair of chukka boots that provides more significant coverage. The classic shoe is a casual favorite—largely because while it does have a laid-back, off-duty vibe about it, it doesn’t feel sloppy or underdressed. Even those that boast a more outdoorsy quality and feel less refined tend to lend outfits a certain pulled together feel. That’s the beauty of the old-school shoe with very modern appeal. You can’t go wrong with Frye Bowery Leather Chukka Boots ($328), which are strong yet understated in a masculine shade of whiskey.

Contrasting Derby Shoes

WANT Les Essentiels Montoro Derby

While derby shoes often have a dressy connotation, your mission this spring is to select footwear that’s a bit more multifaceted in its approach to style. The best pair for the season is a little less polished than a pair of loafers, yet is still remarkably posh thanks to its clean lines and glossy leather. The beauty of the WANT Les Essentiels Montoro Derby ($395) is in its slightly sporty take on refinement. The contrasting line along the heel on the black and cognac versions infuses the otherwise high-brow shoe with a sprightly, relaxed slant. Whether with a suit and tie or a pair of jeans, they’ll look right at home.

Chunky Sole Sneakers

Salvatore Ferragamo Cube Low Top Sneakers

Traditional athletic shoes need not apply if you’re going for a more sporty look this spring. Try a style that marries fashion with function for a more informal appearance. Take your cue from the hundreds of trend-setters and celebrities that pound the pavement daily in sneakers with thick soles. They’re the type of shoes you can really work into your rotation with frequency because they go with so much. While the standard running shoe has limited wear capacity—you really need to be in shorts or jeans to look like you didn’t get dressed in the dark—a shoe with a thicker sole is considerably more versatile, wearable, and practical for your lifestyle. Wear them to your casual office, your afternoon coffee run, or your weekend lunch date. Take your cue from these Salvatore Ferragamo Cube Low Top Sneakers ($530), which illustrate how easy it is to rock a low-key sneaker with a more fashion-forward vibe.

Effortless Slip-Ons

Ted Baker Alador Cupsole Trainers

We all need at least one pair of shoes that we deem ever reliable go-tos before we head out the door for a quick errand run. While for many that tends to be a pair of trusty sneakers, more and more are embracing the comfort of a pair of slip-on shoes. These aren’t the basic, boring, and bland shoes you wore when you were a kid because you couldn’t tie shoelaces just yet. They’re inimitably well designed, with details that set them apart—think suede accents, leather uppers, thoughtful color palettes, and comfortable materials that make them contenders for the season’s most beloved shoe. Give the Ted Baker Alador Cupsole Trainers ($150) a shot if you’re in the market for something that looks just right with cargo shorts, swim trunks, jeans, and khakis alike.