What to Wear with Knee High Boots: The Luxe Styling Edit

What to wear with knee high boots is the style question of the season – and for good reason. These versatile high boots strike the perfect balance between elegance and edge, pairing effortlessly with everything from mini skirts to denim jeans. 

This guide explores how to wear them across seasons and occasions, featuring Mallets iconic Alexandra Knee High Boot in black leather.

TABLE OF CONTENTS

• Styling Knee High Boots With Dresses
• Styling Knee High Boots With Skirts
• Styling Knee High Boots With Jeans
• The MALLET Alexandra Knee High Boot
• Styling FAQs

Styling knee high boots with dresses is one of fashion’s most quietly powerful moves. The key lies in contrast: grounding soft fabrics with structure, balancing silhouettes, and playing with height and texture.

Which Dresses Work Best?

• Slip Dresses: The softness of satin or silk against the structure of leather knee boots is a contrast that always works. Add a tailored coat or an oversized blazer for that off-duty-editor energy – effortless, but intentional.
• Maxi Dresses: Longer lengths bring movement and drama. Opt for styles with a side or front slit to let your boots show through, keep it sharp underneath with heeled knee boots to elongate the silhouette.
• Denim or Shirt Dresses: Slightly utilitarian, slightly refined. These sharper silhouettes work best with structured high boots in black or brown leather. Throw on a trench coat to pull it all together as a clean, modern uniform.
• Sweater Dresses: Effortless and weather-appropriate. A slim or ribbed knit dress with flat knee boots or a subtle block heel looks intentional without trying too hard. It's a winter staple that still feels put-together.

When to Wear It

• Workwear Refresh: Choose a midi-length sweater dress with black knee boots and a tailored coat. Smart, not stuffy.
• The Midweek Dinner: A black slip or midi dress paired with leather knee boots delivers impact without needing accessories.
• The Sunday Walk (That Might Become Brunch): Try a soft maxi dress with flat knee boots and a trench for a comfortable but composed silhouette.

To style knee high boots with skirts is to understand balance.  It’s a pairing that offers freedom in the silhouette – long, short, structured, or fluid – while your boots bring the shape and a statement.

Which Skirts Work Best?

• Mini Skirts: An iconic pairing with roots in the rebellious style of the 1960s – think Swinging London, Mary Quant, and unapologetic hemlines. Decades later, the mini skirt and knee high boot combo remains just as relevant. Black knee boots with a sleek upper or subtle block heel offer just enough coverage to balance the cut. Add a longline blazer or chunky knit for contrast. 
• Midi Skirts: This is the silhouette that does it all: sharp, flowing, feminine. Pair a pleated or column-style midi skirt with brown knee boots or a leather knee boot for an outfit that moves. Bonus: this look layers beautifully under oversized coats or softly structured tailoring.
• Maxi Skirts: The unexpected hero. A floor-sweeping skirt with a subtle slit reveals just enough of your high block heel knee boots to keep the look grounded. Stick to clean shapes and tonal palettes to keep the drama intentional.

When to Wear It

• Office, but Not Boring: Try a leather or wool midi skirt with a tucked-in shirt and block heel knee boots. Add a blazer and you're done.
• Evening Events: Choose a satin maxi skirt with a side slit, a tucked cami, and heeled knee boots. Add drop earrings, skip the coat.
• The “I Didn’t Plan This” Dinner: A high-waisted midi skirt, relaxed tee or fine knit, and block heel knee boots strike the perfect balance between put-together and unfussy. Throw on a coat if you must, but the boots do most of the work.

If dresses and skirts are about softness and contrast, denim is where knee high boot fashion finds its edge. Whether you’re tucking in skinny jeans, layering under looser leg jeans, or embracing full-length denim, the trick is in the fit, the texture, and the boot itself.

Which Jeans Work Best?

• Skinny Jeans: The most classic pairing for good reason. Skinny jeans tucked into a leather knee boot creates a clean, elongating line. Pair with a crisp shirt and structured coat for something timeless. Or try a knit and oversized scarf to keep it casual but classy.
• Straight or Wide-Leg Jeans: Let the knee boots sit underneath the hem, just grazing the leather. This works best with a slimmer boot shaft and a block heel. Think effortless tailoring up top: a longline coat, relaxed tee, or soft knit.
• Denim-on-Denim: A denim dress or double-denim moment works surprisingly well with western boots or a brown leather knee boot. Keep accessories minimal and let the texture mix do the talking.

When to Wear It

• Day Trips or Travel Days: Opt for soft, straight denim jeans, flat knee boots, and an oversized knit. Add a trench or puffer and you’re done.
• Off-Duty City Days: Try skinny jeans tucked into black knee boots, a chunky knit, and a belted coat. Comfortable, pulled together, and grounded.
• Creative Office Casual: Pair a faded straight-leg jean with block heel knee boots, a blazer, and a fine knit – elevated without being too much.

Should knee high boots be tight or loose?

They should fit snugly around the calf without pinching. A structured fit looks more refined with skirts and tailoring, while a looser shaft can work with layered looks or more casual styling.

Should I size up in leather knee boots?

Not always. But if you're planning to wear leather knee boots over thicker layers (like jeans or socks in winter), consider sizing up half a size for comfort – especially with structured styles.

Can you style knee high boots for spring or summer?

Definitely! Pair them with lighter fabrics and softer palettes. Try flat knee boots with a slip skirt or a denim dress and opt for shades like taupe or brown leather knee boots to keep it seasonal. Breathable materials like cotton, silk, and linen help balance the weight of the boot.

How are knee high boots different from ankle boots when styling?

Knee boots offer more visual weight and structure, which means they work well with longer hems or oversized layers. Ankle boots tend to suit cropped trousers or lighter pieces, to ensure they’re not lost in the outfit.

How do I care for knee high boots to keep them looking their best?

Start with the basics: brush off dust after each wear and use boot shapers to maintain their silhouette. For leather knee boots, apply conditioner regularly and polish when needed to keep the finish rich. Suede boots require a waterproof spray and a soft brush to lift marks. Always store them upright, away from direct heat or sunlight – good boot care starts with good habits.

The Final Word on What to Wear with Knee High Boots

There’s a reason knee high boots never really go out of style. When chosen well and styled with intent, they offer a foundation that can shape an entire outfit. 

They’re a trusty companion that grounds soft silhouettes, elevates denim, and brings structure to even the simplest of looks. Knowing what to wear with knee high boots is less about following trends and more about understanding balance – how to pair shape with texture, softness with edge, and comfort with polish.

This season’s take on knee high boot fashion is all about refinement. The Alexandra Knee High Boot leads the way, but it’s just one part of a carefully considered collection.