Laura Lajiness is a fashion editor and writer living in New York City. Here, she’s sharing her tips for how to wear boots with dresses and skirts (and more).
We may be gearing up for spring, but boots are still majorly in rotation: from knee-high styles to versatile ankle cuts. But as layers start to shed and springier pieces make their way into daily outfit lineups, figuring out the right boot height for every outfit can seem daunting. The truth is, certain boots are better suited to mid-length dresses and skirts than they are cropped, flared, or wide-leg jeans. And when it comes to wearing boots with dressier pant styles like trousers, well, let’s just say it takes a very specific pairing to feel just right. Then, there are trendy boot styles like cowboy and western-inspired silhouettes — those require a balance of modern pieces to offset them in a way that feels forward and fresh rather than too literal (unless of course, you’re going for a country vibe).
From office-approved combos to date night-ready looks, ahead, see four easy-to-wear outfits centered around different styles of boots. Sometimes, height does matter.
Combo 1: Maxi Dress + Mid-Calf Boot
Despite being on the shorter side (I’m 5’4” and change), I prefer longer silhouettes like midi and maxi dresses and skirts. No matter your height, these lengthened hemlines have the ability to elongate your frame, especially with a heeled boot like this mid-calf style from Dolce Vita. Going for a monochromatic look (which also can lengthen your shape) I paired them with an asymmetrically cut maxi dress to flow over the top of the boots just so — a slouchier mid-calf boot or knee-high style also works well with this type of silhouette. To break up my palette, I belted the dress and added in a black bag with gold hardware for a polished finish. This is a look I’d wear to work, for dinner, and even to a daytime wedding.
Shop The Look: Field of Flowers Rust Red Multi Print Long Sleeve Maxi Dress, Mariah Black Snake Print Belt, Wila Gold Earrings, similar bag: Kirby Black Mini Purse,
Combo 2: Straight-Leg Jeans + Slim-Fit Boot
Ankle booties are one of the most versatile styles in any wardrobe, but the principles for how to wear boots with jeans depend on the silhouettes of both. A rigid straight-leg jean is my go-to: it offers just enough room to tuck a slim-fitting ankle or mid-calf boot underneath (I prefer a slightly taller height to avoid peeks of skin when sitting down). A slimmer-fitting boot like these Caty boots also works well under wider cuts of denim but can prove tricky beneath skinny jeans — in the case of the latter, I’d recommend a sturdier boot with a wider shaft to layer over your skinnies. As for the rest of my outfit, I kept things simple by reaching for a black crew-neck sweater and oversized white blazer for business-casual style. Planning my transition to spring, I plucked a woven carryall bag for an unexpected finish.
Shop The Look: Imani White Oversized Blazer, Staying Together Black Button Back Sweater, Palmer Light Wash High Waisted Straight Leg Jeans, Glory Gold Hammered Hoop Earrings, Had Me At Aloha Tan Woven Tote
Combo 3: Midi Skirt + Cowboy Boots
As I’ve mentioned before, midi skirts are a favorite of mine so I’m always looking for ways to freshen up my go-to combos. Right now, I’m totally into the cowboy boot trend, especially modern versions that are a touch sleeker than classically western styles. While I would normally pair a knee-high boot with this ruffled, wrap silhouette, I liked the tougher juxtaposition this slightly wider-at-the-top, heeled Kendall + Kylie pair provided. Also, important: The skirt skims easily over the top of the mid-calf style so as to keep the boots on display without creating an unflattering line (a narrower pencil skirt or body-skimming style would feel a bit awkward and cut off my leg). To finish this ‘fit, I kept things tonal with a mustard yellow top, light brown bag, and gold earrings.
Shop The Look: Belleterre Mustard Yellow Ruched Cropped Sweater Top, She’s Wild Beige Snake Print Wrap Midi Skirt, Perfectly Posh Brown Mini Tote, Wila Gold Earrings
Combo 4: Trousers + Tall Boots
Half-tucking a comfy oversized knit into a pair of rust-colored trousers, I tried my hand at a popular styling trick I’ve witnessed on the street style scene: I tucked the pants into a pair of over-the-knee boots. While I stay away from tall, fitted boots atop skinny jeans (it creates an unflattering sausage-y look on my more muscular legs) I quite enjoy the look of trousers slightly billowing out of tall, slim boots. Because there is more fabric tucked into the shaft of these Allegra James boots, they stayed slouched around my ankles, hitting perfectly at my knee. The pointed toe and high heel also helped to elongate my line–no complaints there! The finishing touch: A sleek vegan leather bag and gold hoops.
Shop The Look: Cozy Cutie Cream Knit V-Neck Sweater, Upside Rust Red Pants, Remix Black Pebbled Tote
(Images via Laura Lajiness)
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