How to wear all-weather boots with: a dress
The design elements that have been lifted from classic hiking boots—like lace hooks and a thick tread—are no less practical when applied to a fashion form. Wear a pair with fishnets and an outfit inspired by ’90s grunge (key elements: layering and plaid) as street-style bait. Biggest bonus: Unexpected weather won’t faze you in the least.
Our favorite way of dressing up a boot is to find a style that isn’t so far on the other side of the spectrum to feel comical. Calf-length hemlines make more sense than minis, and a print like plaid (rather than, say, a floral) fits with the ready-for-anything vibe of the shoe. Got a dress that fits the bill but isn’t winter-proof? Style it with a turtleneck or thin knit.
How to wear all-weather boots with: a blazer
For women that want to add a bit of height, a wedge silhouette is key (and it fits with a more polished outfit). A mega tread is equal parts style statement and traction for less than ideal walking conditions. When wearing these this season, look for outerwear beyond the parka and puffer. A tailored blazer might have more shared DNA with loafers or polished heels, but the juxtaposition against something rougher reads brilliantly.
The office-park topper feels younger worn with light denim and tones down a femme, ruffled lace blouse. Avoid awkward bunching between the pant leg and boot by slightly cuffing your jeans. Don’t overthink it with a thick, symmetrical fold; rather, give it a quick flip up for an unstudied look.
Tucking jeans into boots might be the motion most ingrained in our brains when it comes to dressing for chilly days, but resist. There’s a heritage feel to a classic rubber-rimmed lace-up that deserves being put on display. Pull on luxe cashmere-blend socks and a silky maxi that’s winterized with a big chunky sweater.
Just like the practical rain boot plays against the fluidity of the skirt, so too should the knit you pair it with. The bigger, the better—funnel neck included. To keep a boxy cut from being overwhelming (or looking sloppy), tuck in a single corner.