When it comes to heeled boots, this style is incredibly versatile. Whether you opt for calf hugging sock boots, daring over the knee styles or easy-to-wear ankle, block heeled boots, there’s a pair that will work for all occasions.
When choosing which style of heeled boots works best for you, there are a few things to consider. If you’ve got a busy day of walking ahead, a block heeled boot should offer a good amount of support, or, for more dressy occasions, switch to pointed stiletto styles instead of your best party heels.
It's also important to consider your frame when selecting the best boots for you. As well as pulling together 32 ways to style heeled boots below, we’ve also included advice for styling petite or tall frames. Ready to create some incredible outfits? Scroll down for all the inspo you need when it comes to styling heeled boots like a pro.
32 ways to style heeled boots
1. Tap into the boho trend
If you’re looking to build a boho capsule wardrobe, a great pair of boots should definitely be part of it. Make like this influencer and pair a floaty, floral dress with khaki heeled boots for a look that will tap into the free-spirited nature of the trend and perfectly answer the question what is boho style.
RRP: £358 | With a pointed toe and heel these uber sharp boots are a wardrobe staple that you can hold onto and love for seasons to come. The sleek fit works with dresses, leggings and jeans.
RRP: £140 | The best brown boots outfits work all year through thanks to the neutral tone. The block heel plus the wrapped buckle adds interest to the classic design that you can enjoy in any season.
RRP: £440 | A pair of neutral boots will never go amiss and a lighter grey hue is a chic piece to pair with jeans and camel and cream tones. Slip these on under wide legs or team with ankle swinging styles.
2. Play with prints
If fashion royalty Anna Wintour is a fan of heeled boots, you most definitely should be. This look is all about elevating classic shapes, she opts for interesting boots and colourways to up the ante on her maxi length coat and almond-toe-heeled boots. Follow her lead and ditch basic black in favour of bolder, brighter finishes for a FROW worthy look.
3. Stick to a colour palette
Dopamine dressing is the trend that promises to bring joy into your wardrobe by embracing fun, vibrant colours. Recreating this look is the perfect way to try out the trend, contrast different coloured pieces from a similar colour palette, like these yellow and tan tones, to easily create a fun, fresh look.
4. Try a platform style
Have a busy day of walking planned but don’t want to compromise on height? A pair of platform-heeled boots are the answer. These place the feet at a less steep angle than traditional heeled boots thanks to the blocky, platform heel, meaning you can add serious inches to your frame with minimal pain.
5. Wear with trousers and a nice top
Jeans or trousers and a nice top are a failsafe outfit formula and we think heeled boots are the perfect footwear to finish the look. Whether you opt for tailored trousers, like this look, your best straight leg jeans or wide leg trousers, a pair of sleek heeled ankle boots will ensure you look put together and stylish.
6. Give florals an autumn spin
If you’re wondering what to wear to a winter wedding, this dark floral look is a great option. The artistic print feels soft enough for romantic occasions while the dark tones make it winter appropriate. Finish with heeled boots rather than sky high stilettos to make sure you can dance all night long.
7. Make a statement in white
While black boots are a staple in most of our wardrobes, a bright white pair can actually be just as versatile. Take this look as an example, as by opting for a bold white boot, she's elevated a simple coat and neutral outfit to whole new heights.
8. Shine in a patent style
For a twist on the classic black boot, try a patent style. The high shine finish gives the boots a runway-ready feel, making them feel much more interesting and expensive. When it comes to styling, think of these as any black boot, pairing them with dark tones for a coordinating feel.
9. Go big with colour
Sometimes you want an outfit that causes maximum impact with relatively simple pieces and nothing will do that better than a pair of red, patent over the knee heeled boots. Paired with a chic mini dress, you’ve got the perfect bottomless brunch outfit idea.
10. Make them office appropriate
If you’re looking for a smart way to wear heeled boots to the office, this midi dress and knee-high boots combo should provide ample inspiration. A polka dot print midi dress feels formal enough for wearing to work, while slouchy heeled boots give a softer contrast than classic court heels.
11. Add a blazer and midi skirt
If you’re looking for a way to introduce print into your wardrobe, get shopping for pieces to recreate this look ASAP. A printed blazer is an easy way to refresh a simple vest top, midi skirt and heeled boots to give the look a more statement feel.
12. Try a thigh high style
Heeled boots come in many lengths, from ankle boots to knee high boots and also over-the-knee styles. If you’re opting for a thigh-grazing style, we’d suggest layering under a midi-length skirt or dress rather than mini lengths for a more polished finish.
13. Pair with a soft skirt
If you’re lucky enough to work in an office that has a non-corporate dress code, we’d suggest trying this look for your next in-office day. The combination of a soft, floaty skirt and more structured heeled boots come together to make this a winning look, while the high neck jumper gives a smart feel.
14. Wear with leather trousers
In our opinion, leather on leather is always a good idea. Matching shades will always look chic, but we love the way this street styler has opted for different tones for her leather trousers and heeled boots for a look that doesn’t match yet still feels co-ordinated.
15. Try a square toed shape
If you're looking for a heeled boot style with a vintage look, square toed styles are the way to go. Alongside the boxy shape, the tan brown colour of this pair also gives a nostalgic feel, which will only get better the more they are worn for a lived in look.
16. Try a utility look
The utility trend is a look that comes around season after season and it’s the perfect pairing when it comes to how to style heeled boots. Whether you opt for a button detail shirt dress, like this stylish street styler, or a jumpsuit, simply pair with either pointed or square-toe leather boots for a smart, sophisticated look.
17. Wear block heels for comfort
If you’re looking for heeled boots that you can still wear for a full day of walking, a block heel style will be your new best friend. Unlike stilettos, which cause pressure to build up on the balls of our feet, block heels distribute the weight better for a more comfortable wear.
18. Refresh your little black dress
There’s nothing quite like a little black dress during party season to ensure we feel our best. If you’re bored of pairing your favourite style with platforms or stiletto heels, why not rework it with a pair of heeled boots. An over-the-knee chocolate brown pair, like this, is a great option but it'll also work with most heeled boots due to the dress's simple style.
19. Try a classic colour palette
A white skirt may seem best suited to spring summer outfits, however this stylish fashion week guest proves it can be autumn and winter-appropriate too. When paired with a chunky grey knit and black knee-high boots it feels cosy and comforting.
20. Wear with top-to-toe colour
While we’re big fans of a top-to-toe tonal look, where you dress in all one colour, it can be a bit overpowering, especially if you opt for a bright hue. Break up your look by pairing it with contrasting coloured accessories, like black heeled boots and your best tote bag, for a slightly more wearable finish.
21. Try a two-tone style
If printed boots feel too much for you, a chic two-tone style like these is a great way to add some fun to your look without the need to go all out. For a cohesive ensemble, follow this guest’s lead and mirror the tones of your boots in the rest of your outfit and accessories.
22. Wear with a jumper and slip skirt
Three wardrobe staples combine to make this a powerhouse look that’s still incredibly easy to wear. Simply combine your best jumper, a satin slip skirt and a pair of heeled boots, for an outfit that can be worn everywhere from the office to after work drinks. When styling, always leave your jumper untucked for an effortless finish.
23. Be bold in snake print
This look most definitely isn’t for the faint hearted but even if you don’t fancy wearing top-to-toe snake print there are some key takeaways that can make it much more wearable. The contrast of a smart suit and knee high boots is a look that always looks great, so why not switch to classic black and allow the snake print boots to make a statement.
24. Wear with sequins
For a glam look for your next night out, you can’t get much better than a sparkly sequin suit and heeled boots. For extra coverage, add a black bodysuit under your blazer or try a satin camisole for a chic texture clash.
25. Go chic in kitten heels
Kitten heels have a bad reputation, but this boot trend is one that is here to stay for the foreseeable, and if you like a low heel but still a little height, these are for you. Pair them with tailored separates, like this street styler, for a modern take on the nostalgic style.
26. Try a bold boot
If you need proof that a brightly printed boot can totally transform your outfit, save this look to your outfit planning Pinterest board. We love how the influencer has paired street-ready basics, like an oversized t-shirt with a glam flattering midi skirt and statement boots to create a look that feels different and cool.
27. Go tonal in chocolate
If you invest in one colour for the season ahead, make it chocolate brown. We’ve pulled together the best looks that prove brown is the colour of the season, but this look alone should convince you to add a brown midi dress and matching heeled boots to your wardrobe ASAP.
28. Keep it chic and simple
Sometimes the most simple looks can look the most elegant as this back to basics outfit proves. A chic high neck maxi dress will go far in your wardrobe, easily re-worked for relaxed day events and also elegant evening affairs. To finish, a heeled boot is a great option, offering both style and comfort.
29. Wear with a floral dress
For an easy everyday outfit, a floral midi dress and heeled boots make the ideal combination. While ankle boots, like this, work great for sunnier days, a knee length or over the knee style will keep you extra warm in cold weather. Don’t forget to top it off with a chunky cardigan for extra cosiness.
30. Pair with tights
Need to make your heeled ankle boots cold weather appropriate? Layering a pair of tights under them will keep the cold at bay. We’d suggest sticking to the same colour tights as your boots for a leg lengthening effect.
31. Avoid basic black
If you opt for a classic heeled boots shape, like this square toe block heeled style, you can afford to push the boat out when it comes to choosing the colour. We love this influencers cherry red tone for a style that feels unique yet still wearable.
32. Add height to a maxi
While maxi dresses undoubtedly look great and make a smart style choice for effortless dressing, if you’re petite you may often find they’re too long and drag along the floor. Rather than opting for uncomfortable heels, pair your dress with heeled boots for added height without compromising on comfort.
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