20 May 2024

Long boots have long been a fashion favourite, although pushed aside in recent years by the shorter boot, they’re back in 2024 more stylish and versatile than ever. From sleek knee-highs to edgy over-the-knee styles, long boots can elevate any outfit, whether you’re dressing for work or a casual day out. Here’s a comprehensive guide on how to style long boots with dresses, skirts, and jeans for every occasion.

Long Boots with Dresses: Chic and Feminine

Long boots paired with dresses create a chic and effortlessly feminine look. This combination is perfect for transitioning from day to night, making it a go-to for various occasions.

Work, shopping, lunch with the gals.

This chic black dress pairing is ideal for the office, casual meetings, or a day out shopping. The Evermore Knee High Boot from Overland with its low heel will ensure all day comfort, and who doesn’t love an all-black look.

Evermore Knee High Boot: Overland (Merchant)

Dress: Mineral from Farmers

Bag: Farmers

Sunglasses: Sunglass Style

Weekend outings and casual gatherings.

A flowy denim dress paired with long boots offers a perfect blend of casual and chic. This look is effortlessly stylish and can be dressed up or down depending on the occasion. In this look we’ve paired this gorgeous Farmers denim dress with the Overland Sinclair Wide Knee-High Boot and added accessories to match to tie the whole look together. For cooler days add a full-length cream coat or keep it tonal with a denim jacket.

Sinclair Wide Knee-High Boot: Overland (Merchant)

Dress: Whistle from Farmers

Bag: Pagani

Ambre sunglasses: Sunglass Style

Long Boots with Skirts: Versatile and Trendy

Styling long boots with skirts can range from office-appropriate to weekend-ready. The key is to balance the length and style of the skirt with the boots.

For work, pair a midi length pencil skirt or your go-to pleated skirt with a classic knee-high boot to create a sophisticated and polished look. Add your favourite knit and blazer for warmth in the cooler weather.

Shoes: Overland (Merchant)

Clothing: Farmers

Bag: Pagani

Sunglasses: Sunglass Style

Dinner Out
To achieve a contemporary and chic look, mix textures and play with proportions. Here we have paired a midi satin skirt with a cashmere knit and added the fab Sinclair Wide Knee-High Boot and a cream crossbody bag. Layer with a cropped jacket in wool or leather to give it some edge. This look can be changed out for a A line mini skirt and a full-length coat for another on-trend look.

Boots: Overland (Merchant)

Skirt: Glassons

Knit: Farmers

Bag: Overland

Sunglasses: Sunglass Style

Long Boots with Wide-Leg Jeans and Cargo Pants: Bold and Beautiful

Fashion is all about making bold statements, and pairing long boots with wide-leg jeans and cargo pants is a trend that screams confidence and chic sophistication. Here’s how to master this look and turn heads wherever you go.

Work or weekend shopping.
Wide-leg jeans have been around for a few years now and when paired with knee-high boots, they create a stunning retro-inspired silhouette and extra warmth in winter. High-waisted wide-leg jeans elongate your legs, and the boots add a touch of elegance. Tuck in a fitted blouse or top to balance the volume of the jeans.

Boots: Overland (Merchant)

Jeans: Glassons

Blazer: Farmers

Top: Farmers

Bag: Platypus

Sunglasses: Sunglass Style

Weekend with the girls!
Brunch, lunch, vineyard tour, you name it this look has your girls trip covered! This combination blends practicality with a touch of elegance. A fitted top or a knit tucked-in creates a balanced silhouette, while a structured handbag and tonal accessories complete the outfit.

Whether you’re going for a retro-inspired look or an edgy, utilitarian vibe, the key is to balance proportions and play with textures.

Boots: Overland (Merchant)

Clothing and Hat: Farmers

Bag: Pagani

Sunglasses: Sunglass Style