As August closes out and the autumn approaches, I thought it would be a good time to look at some fashion ideas around what dresses to wear with knee high boots. It’s the perfect combination, whether you’re headed out for everyday wear, a date night, or an evening out with friends, pairing dresses with knee-high boots is a great look. You’ll look stylish, keep warm, and if you choose the right dress and knee boots combo, you’ll be able to enhance and celebrate your gorgeous shape.
Dresses To Wear With Knee High Boots
Maxi Dresses
In a daring nod to Anne Hathaway’s outfit, a maxi dress matched with heeled leather knee-high boots can create you an elongated, sophisticated silhouette. You’ll find that if you use a tie-belt or pick a dress with a defined waist, you’ll have a shaping and flattering look on your hands.
Midi Dresses
Midi hem just brushing the top of the boot, particularly tall boots, creates a graceful leg line which is both balanced and chic. It’s perfect for those who don’t want to show too much or those looking for a more modest cut. Take a look at these Chums dresses for older women, which layer beautifully with a heel and a smart jacket or bolero. Midi dresses work really well with block or kitten heels.
Mini and Jumper Dresses
You’ll find that mini lengths look fab paired with snazzy leggings or opaque tights, especially in cooler weather. A cropped coat accentuates the waist and elongates the legs. Try a jumper or sweater dress paired with knee high boots for the perfect combination, which will see you right into winter.
Shirt Dresses
There are so many different styles of shirt dresses out there, so try a few on and see which ones you love the most. You could go for a classic denim look or even a pinstripe shirt dress and pair it with a gorgeous pair of knee high boots. It’s perfect for everyday wear as well as transitioning from day to evening with just a few extra accessories.
Boot Top Trends
Leather riding boots bring timeless equestrian flair. These look great dressed up with tailored outfits or even tweed. A classic look indeed.
You’ll find that a funky pair of cowboy boots will pair amazingly with floaty or denim dresses.
For shorter boot styles, Chelsea and chunky boots can add a boho or edgy vibe to midi or slip-dress combos.
I adore textures like suede in a pair of boots. Classic black leather, or warm browns, are perfect for the autumn and winter and pair with rich winter tones like caramel or burgundy.
Styling Tips
Why not try something different with a monochrome look? You can match your dress and boot colour (e.g., burgundy dress and burgundy boots). You’ll find this creates a long, lean line which is both modern and elegant.
I love to use tights when I’m picking dresses to wear with knee high boots. Tights give you both contrast and coverage. Sheer or opaque tights tone down the contrast between a mini dress and boots. They also give you the effect of longer legs. Tights don’t have to be boring; there are so many different colours and patterns out there that will look fabulous paired with the right boot and dress combination.
Dresses with slits are bang on trend at the moment. You’ll find that slits show just enough boot. This is stylish and chic at the same time.
You can use layers cleverly. I’d suggest experimenting with oversized jumpers, tailored blazers, or suede jackets around a dress and boots ensemble. This is particularly good for curvier figures as it will help to define your waist, and you can choose pieces that are the perfect fit for you.
You should always keep the height of your heels to a height that you are comfortable with. Block or wedge heels can be both stylish and supportive. They’re ideal for everyday wear and look on point with a jumper or shirt dress.
Five Top Styles
Tea Dresses
A tea dress is perfect for the transitional period between summer and winter. Add leather riding boots or Chelsea boots. For colder days, you can add an oversized jumper or a blazer. You’ll find this is the perfect combination for a cosy and chic look.
Smock Style Dresses
Smock-style dresses pair perfectly with suede or leather knee-high boots and opaque tights. I’d suggest layering up with a leather jacket for a bold contrast against the feminine print and style.
Belted Shirt Dresses
Shirt dresses can be paired with chunky boots for an edgy look. You can also use boots with a block heel for a dressed-up take on a shirt dress.
Turtle-Neck Dresses
High necks or turtle neck dresses pair perfectly with sleek black leather knee-high boots. You can add a long coat, something like a trench coat, for extra styling points.
Velour Dresses
Velor dresses are ideal for a more dressy occasion. Add to your glam look with a pair of high-heeled boots, stiletto or kitten heel, if you are comfortable walking in them. Add a pair of dark opaque tights or something with a bit of sparkle for extra glamour.
Dresses To Wear With Knee High Boots
The great thing about shopping for dresses to wear with knee high boots is that there is no one body type which makes this combination look fabulous. You should try on different styles, textures, colours and patterns to see what makes you feel fabulous and confident. Just because one particular style looks good on one body, it doesn’t make it the right choice for you. Try out mini dresses, midi dresses or even maxi styles with different boot combinations and see which style you prefer. Don’t be afraid to move away from the skinny jeans and high boots outfit choice that the fashion industry had everywhere last year. A pair of knee-high boots simply paired with a black mini skirt, midi skirt, maxi skirt, pinafore dress, feminine dress, or longer dresses can give you the wardrobe staple you’ve been looking for.
Some of the combinations are better for everyday wear, and some you’ll find will be perfect for evenings out with your other half or friends. Buy yourself a few boots and dresses and see which ones make you feel fantastic. I’d suggest mixing textures, playing with layers, and trusting that your style is yours and totally valid. Try your outfit with black tights, sheer tights, leggings or footless tights. Wear what you love the look of. Don’t just stick to black knee high boots, experiment with your boot style, heel height and colour. Brown boots look fabulous and offer a timeless look. Not a fan of brown knee boots, why not try red boots or something with animal print? Stiletto boots with animal prints and gold accents are the perfect way to take a casual look and pair with the latest fashion trends.
Sometimes the plainest dress can be layered with a fabulous jacket or blazer and the best boots, and you’ll find that this look becomes one of your favourites. Try something new this winter and see which style of dress suits you and your boots. Arm yourself with an autumn and winter look which will see you right through to spring. You’ll be warm, stylish and loving every minute of your fantastic boot and dress combination.
Feeling confident in what you’ve paired together is key. You’ll look radiant and chic with a confident smile on your face. Everyone will notice, and you’ll feel wonderful!