Category: how to style

Fall style is all about layers and boots, so if you haven’t yet, now is the time to pull out your knee high boots!

Wearing them with skinny jeans is always an easy go to outfit but if you want to dress things up, here are 15+ ideas on what dresses to wear with knee high boots.

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Knee high boots paired with dresses create the perfect fall outfits. You feel put stylish, put together and appropriate for the ups and downs of the weather. There are so many different styles of dresses that really look great with knee high boots!

If you are looking for ideas on what dresses to wear with knee high boots, keep reading for lots of inspiration on what to wear!

Adding tall boots, cute/cozy layers and accessories can even turn some of your favorite dresses during warmer months into Fall ready looks.

Here are some previous ways that I have styled classic knee-high boots:

Ruched Bodycon Dress with Knee High Boots

I have this style of dress in multiple different colors and absolutely love it. It is flattering on every body type with the ruching detail, and when paired with tall boots it really feels effortlessly pulled together.

I styled the black ruched dress with black boots and layered different cardigans for a cozy touch. This is a great way for a way to wear a black outfit, without wearing all black.

Drop Waist Dress with Tall Boots

I love the drop waist silhouette style of dresses and they look amazing with thigh-high boots! I paired my dainty floral printed dress with tan boots, a neutral colored cardigan and a pom knit hat.

This is definitely the kind of outfit I would wear all season long. This is a stylish look that would be perfect for all of the Fun fall activities!

Shop dropwaist dresses to wear with boots

Floral Mini Dress with Over the Knee Boots

The older I get the more I really try to make use of the items I have in my closet. Floral dresses are something I wear a lot during the Spring/Summer but they are a great option for Fall as well!

When paired with over the knee boots and cozy layers, your pretty floral dress turns into the cutest Fall look.

I paired mine here with a coat but this look would also be so cute with a blazer or even a chunky knit worn over the dress to give the appearance as if you’re wearing a skirt.

shop floral mini dresses

Outfit inspiration for dresses and knee high boots

Here are some more different outfits and different styles of dresses that would look great with knee high boots! These are definitely on my list to recreate this season.

Flowy Dress with knee high boots:

I am absolutely obsessed with this look! I love the flowy white dress paired with the brown boots. This is the perfect example of your pretty white summer dresses being able to be re-worn in different seasons!

This look would be so cute for family photos or a girls night in the fall. A pair of knee-high boots is a fall staple for all occasions.

Off Shoulder Dress with Knee Boots:

I always love the look of long sleeve off shoulder dresses as I think they are so flattering with the pop of skin. This outfit ideas would be a great option for a fall date night outfit. It looks so cute with the tan boots and I think would also look great with slouchy boots as well.

What a great way to transition to your winter wardrobe as well, with the layering of the scarf. Just add a cozy warm coat and you are set!

T-shirt dress with knee high boots:

What a great casual look! A t-shirt dress is a wardrobe staple! Most of us already have one in our closet and I typically wear mine during the spring or summer but I saw this idea to pair the t-shirt dress with knee high boots and I just love it!

It looks great with a belt around the waist and the pop of the white boots. This is so stylish and on trend for the season. Another outfit idea for the white boots would be a an oversized sweater with denim jeans!

A-line dress with knee high boots:

Another great way to style dress from warmer months for fall. These a-line dresses are so cute and I love it paired with the tan hat and boots.

This would be cute in all different colors and would even look great paired with black tights and black boots for a more dressed up feel. This dress would be cute paired with different type of boots from ankle boots to over the knee boots and even combat boots!

Embroidered dress with knee high boots:

For a boho feel – try pairing an embroidered dress with slouchy knee-high suede boots! This is on the top of my list for an outfit to recreate and the perfect casual outfit for the season and for everyday wear.

What a fun look for Fall family photos and Fall activities. If it’s chillier, just layer with a long coat!

Lace dress with knee high boots:

The perfect date night or cocktail party all black look! A lace black dress is a closet staple for me and I just love the feminine look with the over the knee boots.

It looks so ute styled with a black leather jacket/moto jacket as seen above and I think it’d also look great with a long blazer for a work event.

Blazer dress with knee high boots:

Do you love the current trend of blazer dresses as much as I do?! This whole look is so stylish and I really love the neutral color palette.

You could recreate this same look with different colors, such as a black blazer and black over the knee boots, or a colorful blazer and tan boots. The options are endless!

Blazer dress with knee high boots:

Shirt dresses are another wardrobe staple in my mind and you really can style them so many different ways. Wear them on their own, layered with the cute pullover or chunky knit, or top with a cute jacket. It’s a cute way to wear a dress that looks like a mini skirt but isn’t!

The shirtdress paired with white boots is such a pretty and unexpected look for Fall. This is something I definitely am going to recreate myself this season. I think this kind of outfit would be a great option for work or dinner out. It feels chic and feminine.

Skater dress with knee high boots:

Skater dresses have such a flirty feel and this a great option to add a feminine look to your knee high boots! I love it paired with the big chunky plaid scarf to add different textures, or as an easy way you could wear it on it’s own with a chunky necklace.

This kind of outfit could be worn to so many different occasions/events and is a go-to Fall outfit for me. Skater dresses look great on all body types and also look so cute styled with tights for cooler months!

Midi length knit dress with knee high boots:

This is a great comfortable look, yet still so chic. Midi-length dresses are great for petite ladies. If you are on the shorter side, maxi lengths can typically be too long.

This knit midi length dress with knee high boots is such a chic look!! I love the black leather boots to contrast off the knit style but really most boot styles would work with this outfit.

If you don’t have a knit dress you could always recreate something similar with knit pencil skirts and a sweater tucked into it! This look would be cute with ankle boots as well.

Bodycon dress with knee high boots:

If you’re looking to wear knee high boots for date night I think a body con dress and a long cardigan is the best choice! It is sexy but still cute and cozy and really flattering. I love it styled like the above with all black and the white sweater. A black dress is always my go to for date night and it is just such an easy way to be dressed up for a night out while still being comfortable!

Sweater dress with knee high boots:

If you don’t have a great sweater dress that you love that is one essential piece I think every woman needs for Fall/winter and it is my favorite way to wear knee high boots! You could create this look with an oversized knit sweater as well!

The chunky knit instantly gives me fall feels and is truly the perfect fall pairing. You can layer it with a long coat, a long cardigan, a moto jacket, flannel shirt or just on it’s own! I love the all neutral color palette shown above.

I hope this helped provide inspiration with what dresses to wear with knee high boots!

Looking for more style inspiration? Don’t miss these posts below!

How to Wear a Maxi Dress in the Fall

20+ Easy Ideas to Style a Black Pencil Skirt

A black pencil skirt is a wardrobe essential. It is simple enough to be worn on it’s own and to be styled multiple different ways. It easily transitions from day to night and throughout different seasons.

Pencil skirts are flattering on all body types there are so many styling possibilities! The higher waist fit helps to highlight Nautral curves and give you an hourglass figure.

I love dressing up pencil skirts for work events and even date night but there are so many ways to style it casually as well! Here are 20+ ideas on how to wear a black pencil skirt!

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How to wear a black pencil skirt:

These pencil skirt outfits can be worn for so many different occasions. The best part of these outfits are that they are not complicated at all, you start with a straight skirt and different tops and you’ve got so many outfits to work with!

Black pencil skirt outfits for all body shapes

These styles can be worn for women of all ages and all body types. If you on the shorter side and looking how to style for a petite frame, you can look for petite skirts that run a bit shorter (hits above the ankle) or even add a top over a slim dress to create the same look.

#1 Denim Shirt

Along with the pencil skirt, a chambray shirt is a wardrobe essential! Pair them together and you have a perfect match to take you from day to night.

I love it paired with the leopard heels and it is so cute with a camel colored coat overtop for a pop of color. This is a great look for Fall/Winter or you could do a shortsleeved denim top for Spring/Summer.

#2 Simple White Blouse

I love the idea of a crisp white shirt with a long pencil skirt. This is a classic piece that you likely already have in your closet and when paired with a tight pencil skirt it is super flattering and perfect for work or even date night.

The sleeves on the tops shown add a nice feminine and flowy detail that really complements the tighter fit of the pencil skirt.

#3 Plaid/Flannel Shirt

Pairing a pencil skirt with a plaid shirt is such an effortlessly fun way to style it. I love this combination and how she knotted it below to show her lace top underneath – so cute!

It’s really easy to work with different top combinations and with the right accessories you are set for work to happy hour!

You could also wear a flannel shirt buttoned up and tucked into the skirt or an oversized flannel left open over a crop top! The possibilities are endless.

#4 Layered Sweater and Collared Shirt

This is a great option if your work in a corporate office setting. Layering a pullover sweater over a button down shirt is so chic and ultra stylish.

You could do this with neutral colors or even pair a printed button-down underneath a bold colored sweater for a fun look.

The simple shirt paired with the midi pencil skirt is great for a straight to a pear shaped body type.

#5 Simple Pullover and Sneakers

For a casual pencil skirt outfit, pick your favorite cozy oversized sweater and sneakers and you’re good to go to grab lunch!

This is another effortlessly cool way to style a typically more preppy/put together skirt. I find stretchy pencil skirts to be really comfortable so I would be more than happy running errands in an outfit like this.

#6 Knotted T-shirt and Booties

Knotting a simple t-shirt is a great way to amp up simple basics. I love it paired with nude booties for a cute fall look.

This knotted technique would look great with a graphic tee, tie-dye tee or tank top as well.

The long black skirt with the slit is great as it also makes it easier to walk in! Both of these are a staple piece that you’ll wear a lot with other pieces as well.

It’s the perfect casual look if you wear it with sneakers and add a baseball cap!

#7 Sweatshirt and Heels

Dress up a sweatshirt with a faux leather pencil skirt and heels!

I love this way of styling a pencil skirt because it feels put together and not too forced. This would be another outfit that would be totally great to wear to the office or even if you work from home! Comfortable but still put together.

I’d love this styled with a chic wool coat and scarf for cooler months as well.

#8 Add a belt

The use of belts really helps to accentuate your natural curves or give you the illusion of curves. The belt really accentuates the flattering fit of the higher waist on a pencil skirt.

When styling with a belt I would stick to more neutral colors overall and let the belt be the focus. I love the oversized gold buckle as shown in the inspiration photo below.

This would also be cute if you have a designer belt that you want to showcase!

#9 Graphic Tee

Graphic t-shirts can be styled in so many ways, and with a pencil skirt is no exception! This is the perfect Fall outfit.

I love it with the cute little bag and the pointed toe suede booties as shown in the photo below. This would also be really cute with a faux leather pencil skirt.

#10 Silky Cami

A silky cami really elevates a black pencil skirt. Top it with a blazer for office wear and on it’s own for a cocktail party. This would also be great if you had a bodysuit with this type of silky material to pair with the pencil skirt.

#11 White Tee and Denim Jacket

This is one of my favorite ways to style a pencil skirt! So easy and you likely already have all of these items in your closet.

Just choose your favorite white tee/tank and go-to denim jacket. Add heels, boots, flats, sneakers or whatever else fits best for your occasion and you’re good to go!

#12 Monochrome

Pairing a black pencil skirt with a top, coat and shoes in the same color is so chic! This is a street style look that is easy to replicate and really is stylish.

I love the cozy gray sweater and chic gray coat paired with fun gray sneakers. You could also do this with a camel colored sweater, coat and booties for a cozy Fall look.

#13 Peplum Top

Peplum tops are so flattering and when paired with a pencil skirt is really gives you an hourglass figure. I love the feminine aspect to a peplum top and it is a nice contrast to the body hugging pencil skirt.

#14 Black Tee

Pairing a black tee with a knee-length pencil skirt almost gives the illusion of a little black dress! This is so chic and depending on your jewelry and shoes could easily be styled for day or night and different occasions.

Simple black heels and pretty gold jewelry make this perfect for the office during the day and drinks at night.

#15 Black Turtleneck Sweater

I love wearing turtlenecks in the colder weather and I think they look so pretty paired with a pencil skirt. Just add some nude heels and you’re good to go for the office or happy hour.

#16 Trench Coat

Pairing a trench coat over a pencil skirt is another one of my favorite ways to style it! It looks so chic (I love the olive color in the inspiration photo shown below) and is great for Fall coming up. It would also be cute with a crop top underneath the trench coat!

#17 Cardigan and Knee High Boots

A great option for the modern fashionista – wearing a cardigan all buttoned up as a top and pairing with knee high boots.

#18 Floral Blouse

A floral blouse is something you typically already have in your style and it adds feminine little details and a pop of color to a simple pencil skirt!

The possibilities are endless with floral blouses just based on the silhouette of the various tops – I think an off the shoulder style would also be so pretty!

You could also pick polka dots or stripes as a fun print with the pencil skirt if the floral option isn’t your style!

#18 Knotted Button Down and a Hat

I love the idea of doing a knotted button down for an effortless feel with a pencil skirt. As seen below, she styled it with simple scrappy heels and a cute hat! This would be a great outfit to transition into Fall weather.

#19 Leopard Print

A classic print like leopard is the perfect match for a black pencil skirt. Just add your favorite high heels for a sleek office ready look.

#20 Florals for work

A classic combination for work. Just pair it with a classic pencil skirt and you’ve got a flattering and chic outfit. This is also a great outfit to look chic for the winter and not freeze!

Need more style inspiration? Don’t miss the below!

How to build a winter capsule wardrobe

The Best Dresses for Petite Women