Put your best foot forward and navigate the world of boots with our ultimate guide – who says you can’t wear them in tropical climates like Singapore? From the modern peep toe to classic Wellingtons, we’ve rounded up some of our favourite designs, along with guide on how to style them.
Ankle boots are one of the most versatile styles of boots, and can be worn in any weather – even in Singapore’s tropical one. They cut just above the ankle, and can feature anything from a low chunky heel to a sexy stiletto. Simultaneously Parisian chic and Americana cool, this style of boot is perfect for all leg shapes.
Style tip: You can rock the ankle boot any way you want, whether it’s paired with skinny jeans or a midi-dress. For an urban vibe, style your ankle boots with a pair of distressed cuffed-up jeans.
Featured: Heel Ankle Boots, $89.90, Pedro
Who doesn’t love a wedge boot? Stylish and oh-so-comfortable, you could walk miles in them without complaint! Available in all kinds of lengths, ranging from ankle to mid-calf to over-the-knee, we love a pair with a pointed-toe or hardware detailing.
Style tip: The wedge makes the overall shoe chunkier, lending an edgy vibe to your look. Pair ankle-high wedge boots with a pair of skinny jeans in a similar colour to make your legs look instantly longer, or with a turtleneck sheath dress for a modern style.
Featured: Jorian Up Boot, $356.29, Schutz from Revolve
Think rubber boots that were first made popular by the first Duke of Wellington, eventually becoming an outdoor and hunting staple for British aristocracy in the 19th century. Also known as gumboots or rain boots, Wellingtons of the 21st century have come a long way (style-wise) from the chunky pieces of rubber back in the day. You can find several styles, from printed floral to a sleek matte black version that’s perfect for rainy days.
Style tip: Pair with skinny jeans and a slouchy sweater for a chic, rain and/or snow-friendly look, and accessories with scarves and beanies to pull the entire look together. To add a pop of colour, wear knee-high socks that just peek above the tops of your wellies.
Featured: Hunter Original Tall Wellington Boots, $303.99, ASOS
Exactly as they are named, cowboy boots refer to a specific style of riding boots that were historically worn by cowboys. Easily identified by the embellished leather shaft and rounded tops, this style of boot is traditionally cut off just below the knee, but modern adaptions see the ankle and calf-length variations too.
Style tip: You’ll want to show off the gorgeous design and unique cutting of these boots to the fullest, so pair them with shorter hemlines or with skinny jeans. We suggest styling your cowboy boots with a pleated skirt for an interesting juxtaposition, or with a chiffon, floral maxi dress for a boho-meets-country vibe.
Featured: Lasso Boot, 271.53, Steve Madden from Revolve
A pair of good hiking boots are a fantastic investment, as they serve the double duty of offering proper ankle support when you hike, as well as looking incredibly chic on the streets. Think Timberlands and Red Wings and their foray from actual jungles to urban jungles. Featuring stiffer leather uppers and chunky soles, these are the perfect boots for fall and winter looks.
Style tip: Definitely pair with plaid if you’re looking to capture the essence of autumn, otherwise style with a pair of leggings and a baggy sweater for that model-off-duty vibe.
Featured: Women’s Euro Hiker Boot, $299, Timberland
A variant of the ankle boot, Chelsea boots are close-fitting, ankle-high boots usually with a rounded toe and a low heel. They usually have a loop of fabric sewn on the back of the boot to allow you to easily pull them on, and feature a panel of stretch fabric on the sides, allowing a slight give despite the slim cut.
Style tip: Definitely try them on before buying if possible, as the combination of stretch fabric and slim-cut could mean a potentially ill-fitting pair of boots! When you’ve found the perfect pair, style them with skinny jeans, or with sheer leggings and a dress combo.
Featured: Rockstud M-Way leather Chelsea boots, $2,607, Valentino Garavani from Net-a-PorterALENTINO GARAVAN
Also called open toe booties, this style of boot showcases a toe-baring design and can be of any length, from ankle to over-the-knee. The peep-toe boot is extremely versatile and can be worn for both formal and party settings (while letting you show off your latest pedicure).
Style tip: We love a mesh open toe bootie with cuffed, distressed boyfriend jeans and a basic t-shirt for casual Fridays (blazer optional), or a crushed velvet style with a sleek dress that’s perfect for dominating both in the boardroom and the bar.
Featured: x REVOLVE Delilah Peep Toe Bootie, $356.29, Michael Costello from Revolve
Sexy and chic, stiletto boots are basically any length of boot featuring a stiletto heel instead of the classic block heel. Stiletto boots are a great option to instantly elevate an outfit, and are so versatile you can wear them for almost every occasion.
Style tip: If you want to rock this style even in the strictest work environments, opt for an ankle cut stiletto boot and pair it with a pencil skirt or cigarette pants, and a tailored shirt and blazer. If you’re dressing for a night out with the girls, think of a pair of stretchy sock boots and a bodycon dress.
Featured: Pointed-Toe Stiletto Heel Ankle Boots, $85.90, Charles & Keith
Traditionally designed for horse riding, riding boots are a classic that looks good with pretty much everything! They are typically knee-high in length (so as to protect riders from chaffing) and feature a distinct heel that prevents the rider’s foot from slipping through the stirrups. Even if you’re not mounted on a horse, these features come together for a distinct style of boot that is incredibly versatile.
Style tip: It only makes sense to definitely try the equestrian look, given the history of these boots! We recommend them with a perfectly tailored blazer and slim-cut jeans for a super polished look.
Featured:+ NET SUSTAIN The Riding leather knee boots, $1,296, Toteme from Farfetch
This style of boot stops 1-2 inches below your knee, typically hugging the widest part of your calf. Made super popular in recent years by the likes of the Kardashians and Kanye West, forget the myth that curvier girls can’t rock this style of boot.
Style tip: The easiest way to style calf-length boots is with a dress that cuts just above the knee, as this ensures a good amount of leg is showing to help balance proportions. If you are not into showing off your legs, then wear them under cropped, frayed hem jeans, or a midi skirt for a super chic look.
Featured: Rhys Chelsea Calf Boots, $105, Charles & Keith
Also called above-the-knee boots, thigh-high boots are extremely flattering and are so versatile, that you literally cannot run out of ways to wear them! Whether you opt for leather or suede, flat soles or chunky heels, these statement shoes should be a wardrobe staple.
Style tip: We love a good contrast, so try pairing light-coloured boots with an all-black outfit. You can also pair them with a shorter dress or skirt to allow some skin to show, if the weather gets cooler, simply don a pair of patterned sheer tights for added style factor.
Featured: Stretchadoxa suede over-the-knee boots, $3,132, Christian Louboutin from Net-a-Porter
Elegant, smart and glamorous all at once, every girl should have a pair of knee-high boots in her closet! Ending just below the knee, this style of boot is one of the most flattering, as it gives your legs a streamlined appearance.
Style tip: Pair with a flouncy skirt, tucked into a pair of jeans or under a maxi dress with front slits. If your hemline is shorter, we recommend pairing them with colourful knee-high socks while keeping the rest of your outfit monochrome.
Featured: Gabine Leather Knee-High Boots, $189, Charles & Keith