27 Knee High Boots Outfits for Winter With Midi Skirts and Tights

Paris and New York already know it: the slim pointed knee boot does more for a winter outfit than any coat. Here are 27 looks, in the spirit of Saint Laurent, The Row and Khaite, built around one boot and the skirts and tights that meet it cleanly.

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Hot Pink Mohair Against Black Leather

This is the look that proves a black boot and a loud sweater belong together. The hot pink mohair is big and soft, and the black leather midi skirt ends right at the boot top, so there is no gap of leg and no awkward line.

Pick a skirt with a bit of weight so it hangs straight, and let the sweater sit loose over the waistband. Choose a mohair blend, not a thin acrylic, so it holds its shape and does not shed on the leather.

A cobalt blue top-handle bag is the second shock of color. It reads deliberate, not matchy, and it is the reason a photo of this outfit gets saved.

Cobalt Satin and Gray Tweed

Tweed is the grown-up part, and a cobalt satin shirt is the surprise. Together they look like someone who gets dressed with intent, not out of habit.

Let the gray tweed midi skirt end at the boot top and tuck only the front of the shirt so the satin falls softly. Look for a tweed with a little stretch and a lining, so it does not cling to tights or itch.

A cherry red shoulder bag ties the blue to the black boot without matching anything. It is a bold pairing, and the pointed toe keeps it sharp.

Cherry Red Knit on Chocolate Suede

Red and brown is a pairing that looks expensive without trying. The cherry red knit pops against a chocolate suede midi skirt, and the brown boot melts into the skirt for one long line.

Suede wants a straight cut with a slight flare, ending at the boot top. Check the label for real suede or a good microsuede, because cheap versions shine and crease at the hip.

A butter yellow bag sounds wild and works, because yellow warms up both red and brown. Keep everything else plain and let the three colors talk.

Lime Chunky Knit, Charcoal Pleats

Lime green is the loudest knit you can put over a charcoal pleated skirt, and that is exactly why it works. The pleats move, the boot keeps the leg clean, and nothing looks fussy.

Choose a chunky knit with a slightly cropped shoulder drop so the volume sits above the waist, not on the hips. A charcoal pleated midi should end where the boot starts.

A violet bag finishes the clash. Lime and violet sit opposite each other, which is why the pair looks planned.

Cream Knit and Red Tartan to the Knee

A red tartan pleated skirt to the knee is the cleverest way to wear plaid in winter. The black opaque tights turn the knee into part of the boot, and the cream knit keeps the red from feeling like a costume.

The rule here is simple: the tights match the boot, so the leg reads as one long black line. Look for opaque tights of at least 80 denier so the color stays solid under light.

Let the knit be chunky and slightly boxy. It balances the skirt and lets the boot stay the star.

Fuchsia Ribbed Midi Dress

One piece, one big color, and a boot that does the rest. A fuchsia ribbed knit midi dress is the easy answer for a weekend when you want to look styled with no effort.

Black opaque tights and a black pointed knee boot break the pink with a clean dark line. Choose a ribbed knit that is soft but not clingy, so the dress skims and does not cling.

A brown shoulder bag warms the pink and keeps it from looking too sweet. It is a small decision that grown-ups notice.

Gray Tweed Blazer and Matching Skirt

A matching tweed set is the quiet cousin of the loud looks, and it is the right call for a work day. The double-breasted blazer sits relaxed over the hips, and the midi skirt ends at the boot top.

Buy a tweed with real wool content if you can, since it hangs better and lasts. Keep the shoulder relaxed rather than nipped in, so the set looks current and not 2000s.

A brown top-handle bag is the only accent. It is polished and a little Row, with no noise at all.

Black Turtleneck, Black Leather, Black Boots

Nothing is more Saint Laurent than a head-to-toe black outfit with texture instead of color. The turtleneck is fine wool, the skirt is leather, and the boot makes the leg one dark line.

Tone-on-tone only works when the textures differ, so keep matte wool against glossy leather. A fine-gauge turtleneck sits cleaner under a skirt than a chunky one.

Add a plain black bag and nothing else. The sharp toe of the boot is the detail.

Cream Knit and Plaid to the Knee

A plaid pleated skirt to the knee looks office-ready when the knit is cream and the tights are black. The opaque tights bring the skirt into the boot, so the hem never feels stranded.

Choose a plaid in muted tones, like gray and camel, so it reads as tailoring, not as a school uniform. The knit should be soft and a little oversized.

It is the calmest look in this article, and that is the point for a Monday.

Camel Turtleneck and Rust Corduroy

Rust and camel are close cousins, and corduroy gives the pair some texture. The midi skirt ends at the boot top, and a brown boot keeps the whole outfit warm.

A fine-gauge camel turtleneck stays slim under a belt or a loose waist. Look for a corduroy with a little stretch so it moves instead of bunching.

It is a quiet, autumnal look with nothing that shouts, ideal for an office with a relaxed dress code.

White Shirt and Navy Wool Skirt

A crisp white shirt under a navy wool midi skirt is the classic that never dates, and a tan boot makes it feel fresh. The skirt stops at the boot top for a clean break.

Tan is the underrated boot color, and it works with navy because they sit opposite each other. A poplin shirt with a stiff collar keeps the outfit sharp.

Keep the bag simple and the jewelry small. The boot is the one warm note.

Emerald Satin Pleats and Cream Knit

This is the party-ready version of a midi skirt. Emerald green satin pleats catch the light, and a chunky cream knit makes them easy to wear on a cold night.

A brown boot keeps the emerald warm instead of cold, which is the trick here. Choose a pleated skirt with a soft elastic waist so the knit can sit loose over it.

A cherry red top-handle bag is the daring finish, and it works because red and green sit across from each other.

Mustard Knit and Red Boots

The one red boot is the single bold move, and here it is the whole outfit. A mustard yellow knit over a black pleated midi skirt gives the red something to push against.

Keep everything else black so the red boot stays the focus, and make sure the skirt ends at the boot top. Red leather boots look best in a smooth finish, not a patent one that competes with the knit.

A plain black bag completes it. This is a look people turn to see.

Black Slip Skirt and Cream Cardigan

For a night out, soften the boot with a cream cardigan worn like a top. The black midi skirt keeps the line long, and the cardigan gives the evening a little warmth.

Button the cardigan low and wear it with nothing visible under it, so the neckline reads sleek. Choose a fine merino so it does not bulk at the waist.

Add a small black clutch and gold earrings. It looks like Khaite on a budget.

How to Choose the Knee Boot

Start with the shaft: it should fit the calf without gaping or pinching. Pick a pointed toe and a heel you can walk in, around two to three inches. Black goes with everything, brown suits cream and rust, tan loves navy, and one red pair is the single bold move. Match tights to the boot, not the skirt.

Violet Sweater Dress and Burgundy Tights

Burgundy tights are the secret here. A violet knit sweater dress to the knee looks richer when the legs are a deep wine color, and the black boot ties it down.

Choose a dress with a loose fit so it does not cling, since tight knits date a look fast. Opaque tights in burgundy need a dark boot to stay grown-up.

A mustard bag adds a warm spark. Violet, wine and mustard are a bold trio that holds together.

Zebra Print Midi and White Utility Shirt

A black and white zebra-print midi skirt is the daring one, and a plain white utility shirt makes it wearable. The red boot picks up the energy without adding another print.

Let the shirt hang loose and tuck only the front. Choose a skirt in a soft fabric that swings, because a stiff animal print looks costume-like.

A cobalt blue bag is the one more surprise. With red boots, keep to this single red item and let the blue do the rest.

Gray-Green Knit Set and Leopard Coat

A matching knit top and midi skirt in gray-green is the base, and a leopard-print coat worn open is the loud cover. The dark brown boot ties the two together.

A knit set reads as one long line, which is why the boot top meets the skirt hem so neatly. Choose a mid-weight rib so the skirt does not cling.

A hot pink bag is the final clash. It sounds like too much and looks exactly right.

Black Lace Top and Satin Midi

For a date, go sleek and a little sharp. A black lace-trim top with a satin midi skirt in rust gives a Saint Laurent edge, and the pointed knee boot keeps it grounded.

Rust satin is warmer than black and looks great against the dark boot. Choose a bias-cut skirt that skims, ending at the boot top.

A small clutch and a pair of drop earrings finish the picture.

Cherry Red Blazer and Black Skirt

A cherry red blazer is a dinner-date shortcut. Over a fine black top and a black midi skirt, it looks deliberate and warm, and the boot carries the line down.

Choose a boxy cut that covers the hips and sits relaxed on the shoulders. Red wool or a wool blend holds its color better than a thin polyester.

Add a small black bag and let the red do the talking.

Camel Knit Dress and Tonal Tights

A camel knit dress to the knee with tights in the boot color is the longest-legged outfit in this article. The tights match the boot, and the whole leg reads as one line.

Choose a dress with a loose, drapey fit, not a clingy one, and pick tights in a real brown, not a flat black, so the tone looks intentional.

A rust bag adds a warm detail, and the look stays soft and rich.

Olive Leather Skirt and Cream Top

Olive leather is the color that makes a date outfit feel less obvious. A cream silk-feel top above it keeps the contrast soft, and the black boot cuts a sharp line.

The skirt should be midi and just touch the boot top, so no leg shows between. Choose a lambskin-look leather with a matte finish, not a shiny vinyl.

A tan bag softens the black boot and links the cream and olive.

Red Boots, Black Knit Dress

The simplest date outfit is a black knit dress and one red boot. It is the single bold move, and it needs nothing else to look finished.

Pick a dress that ends at the knee with a slight swing, and wear sheer black tights so the boot stays the focus. Keep the jewelry small and gold.

A red lip would be too much, so pick a neutral bag and let the boot lead.

Tweed Midi Skirt and Black Velvet Top

For a holiday dinner, a rust tweed midi skirt with a black velvet-feel top is rich and grown-up. The boot top meets the skirt hem for one long line.

Choose a top with a small neckline and long sleeves so the skirt can be the star. A tweed with a flecked weave catches the light at dinner.

A gold-toned bag and small hoops finish it, in the quiet spirit of The Row.

Emerald Wrap Top and Black Pleats

For a wedding guest, an emerald green top with a black pleated midi skirt is festive without being loud. The sheer black tights and pointed boot keep the leg long.

Pick a top with soft sleeves and a modest V-neck, so it stays suitable for a ceremony. The skirt should end at the boot top and swing as you walk.

A black clutch and small earrings are all you need.

Burgundy Satin Dress and Tonal Tights

A burgundy satin slip dress is a holiday-party classic, and the pointed knee boot keeps it from feeling summery. Matching tights make the leg one smooth line.

Wear it with a fine knit under the dress so the sleeves are covered and the fabric still shines. Choose a dress that ends at the knee for the boot to meet cleanly.

Gold earrings and a small black bag finish it.

Cream Knit and Chocolate Leather Midi

Cream and chocolate brown are the smoothest pair in a winter closet. A chocolate leather midi ends at a brown boot, and a chunky cream knit makes the whole look soft.

Choose a skirt in a supple finish and a boot in the exact same brown family so the leg reads tonal. Let the knit hang slightly loose at the waist.

A tan bag adds warmth. It is a polished, quiet look for a long dinner.

Hot Pink Knit and Gray Tweed Midi

One last loud one: a hot pink knit over a gray tweed midi skirt, with the black pointed boot as the leg line. The gray calms the pink and keeps it from feeling like a party favor.

Choose a knit with a slightly fuzzy texture that photographs well, and a tweed skirt with a lining so it never clings to tights. The hem should land at the boot top.

A cobalt bag ends the article on a high note and shows how far one black boot can go.

One Boot, Twenty-Seven Ways

The sleek pointed knee boot works because the skirt and tights meet it cleanly. Start with the winter boots guide, then pick your color and go.

FAQ

What skirt length works with knee high boots?

A midi skirt that ends at the boot top is the cleanest option. A knee-length skirt also works when you add opaque tights in the boot color.

What color tights go with knee high boots?

Match the tights to the boot color so the leg reads as one long line. Black opaque tights with black boots is the safest pairing.

Can I wear knee high boots with a dress?

Yes, with a knee-length or midi dress. Keep the hem at or just above the boot top so no awkward gap of leg shows.

How do I stop knee high boots from sagging?

Choose a shaft that fits your calf and has a bit of stretch or a back zipper. Thick tights can fill a slightly loose boot.

Are pointed knee high boots still in style?

Yes, the slim pointed knee boot is a current Paris and New York street-style staple. It looks sharper and more grown-up than a chunky boot.