When the weather gets cold, we all start looking for ways to keep our legs warm while still being able to dress stylishly. Knee high boots are one of the best ways to do this, but you’ll want to make sure that your outfits don’t hide them from view. The key to pulling off knee high boots with dresses is knowing how to layer so that you’re not wearing too many things on top of one another, which will make you look bulky and uncomfortable instead of stylish and cozy.
Ruched Bodycon Dress

If you want to rock the bodycon dress, here’s one style that does the trick! The Ruched Bodycon Dress is at the top of our list because it has a semi-formal, yet flattering look. The deep neckline is both sexy and modest, and the cutout back design looks amazing paired with your favorite pair of boots. To complete this look try some strappy heels or studded ankle boots for a more tough-chic vibe.
Drop Waist Dress

One of the many classic dresses that goes perfectly with knee high boots is a drop waist dress. A slouchy, draped dress will soften the strong lines of a skirt and elongate your frame. This is one of those dresses that always make you feel elegant and ladylike. The beige hue also pairs well with dark brown or black knee high boots for a little contrast.
We hope this has helped you on your quest to find the perfect dress for your fall attire!
Floral Mini Dress

You may be tired of seeing this dress on the list, but the number one thing people wear with knee high boots is a mini-dress. This floral number from Forever 21 has plenty of colors to go well with a variety of colors in your shoe selection. The bright colors might be too cheerful for some occasions, so opt for more somber colors such as reds and blacks if you think it might look better. For just $26, there’s no way you can’t afford to buy this one.
Flowy Dress

If you’re looking for a dress that fits perfectly with your winter wardrobe, this flowy dress is a great choice. It’s light enough to wear in the winter without overheating and the length is perfect for those times when you want to wear your knee high boots. Its unstructured design also adds mobility, which comes in handy when bundling up against the cold or moving around town.
Off Shoulder Dress

Finding a versatile dress that looks great on its own or with jeans and knee high boots is easy. I absolutely love this off shoulder dress because it’s edgy enough to wear to a party, but it also looks great for everyday wear. It even has a slit in the front so you can show off your favorite pair of knee high boots!
T-shirt dress

First, a little refresher on the t-shirt dress. It is a simple but versatile garment that can be worn for any occasion as it is timeless and just goes with everything. T-shirt dresses look great over leggings and booties or can easily be dressed up with stilettos and a cropped leather jacket. They are the perfect dress to take you from day to the night because of how easy they are to wear!
A-line dress

The A-line dress is great for those looking for a more modest knee high look. This style balances well with knee highs, giving the appearance of longer legs and making you appear taller. It also accentuates curves in all the right places, so it’s flattering to many body types. Pairing this dress with thigh high boots will have a similar effect as wearing it with knee highs.
Embroidered dress

A dress like this is the perfect transition piece for fall to winter. The dress is super cute and comfortable but also made of a light weight fabric so it will be perfect when it’s cool outside. It has a v-neck with crisscross straps in the back and comes with a matching belt. The belt features pom poms on either side which are really cute and festive for Halloween or Thanksgiving.
Lace dress

One dress that always goes well with knee high boots is a lace dress. This dress can be worn at all times of the year and is perfect for cold weather. It looks cute over leggings and will keep you warm while showing off your legs. If you are wearing a sweater, don’t forget to pull it up a little bit so it can show off the dress. Wear boots in black or brown for an easy match to this piece of clothing!
Blazer dress

The blazer dress is a classic look that can be paired with almost anything. Give the classic black and white color palette a twist by throwing in a deep red, an electric blue, or any shade you fancy. The best part? You don’t have to pair it with a jacket like its name suggests! It’s versatile enough to go well over leggings, tights, jeans, or whatever else your heart desires.
Shirt dresses

A crisp white shirt dress is an essential every woman needs in her closet. While they can be worn with virtually any bottom and are perfect for workwear, they are still very much a party piece. The following five options will cover your bases whether you’re headed to dinner or out dancing the night away!
Skater dress

This adorable skater dress is perfect for a date night. It’s form fitting, but comfortable. The deep-plunging neckline shows off a little skin, while the vibrant print and playful skirt add some fun to your look.
With this dress, you’ll want to wear high boots to show off that midi length skirt, but because the neckline is scooped low in front and back, stay away from extra tall high heels so you don’t end up with awkward proportions.
Midi length knit dress

Channel your inner disco queen with this midi-length knit dress that provides maximum boogie room to boot. It also has pockets, so you can be prepared for a quick emergency – who knows what your Saturday night could bring! The length of the dress is perfect for wearing over tights, or simply pairing with knee high boots and staying comfy. Pair it with a fuzzy scarf and some statement earrings to give off a voguish vibe.
Bodycon dress

This dress features a stretchy fabric and is tight on the upper body and full on the bottom with a voluminous pleated skirt. This dress would be perfect to wear in the winter with your favorite knee high boots. One of the most popular types of dresses to wear with knee high boots is bodycon dresses because they hug your curves while remaining slim fitting on top.
Sweater dress

This elegant style of dress pairs well with a variety of styles of boots and shoes. A sweater dress is comfortable and has an understated sophistication that will never go out of style. Wear this to work or for a night out with friends, but the flatter the shoes, the better. This is one dress that can be dressed up or down seamlessly.