Here's what to look for in classic footwear
Footwear is a very personal affair, with one woman's frumpy being another woman's practical, and one woman's sexy being another woman's slutsville. However, footwear is also one way in which to express yourself personally ('red shoes no knickers') or introduce a bit of colour or texture into an outfit.
For country wear, serious walking, riding or foul weather, shoes need to be practical first and foremost, and this is the territory of traditional footwear such as brogues, riding boots and wellingtons. All other types of women's shoes emphasise the sexy over the practical (just try running in the average court shoe if you think that's not true).
Women's shoes are generally considered to be sexier the more they differ from men's - differences might include more delicate materials such as fabric, suede or perspex, a flimsy design with cut-away sections, thin straps etc and above all, heel height - the taller the heel, the sexier it is, until at the extremes, you reach the heights of fetish wear. Sexiness comes at a price, however. Arthritis of the knee is on the rise in women, along with double arthritis of the knee, which is almost unknown in men. Orthopedic surgeons are entirely convinced that this is because women wear high heels. So if you value your long-term health, don't wear heels above 3 inches, vary your heel heights every day and spend part of each day barefoot.
In practical terms, most women need a mix of shoes, including practical footwear, everyday shoes that are attractive but wearable and sexy girly stuff for posh.
Stiletto (above left). Named for the knife-like sharpness of its heel, a stiletto is always considered sexy - perhaps rather too sexy for a conservative office in a field such as banking or law, but more acceptable in a relaxed atmosphere such as media. For evening wear, stilettos are a classic choice, in suede or fabrics such as satin or brocade. However, they can damage floors and cause strain to the back and not all women feel comfortable in them. If you can't walk in stilettos, choose stiletto-heel boots, which gives more ankle support, or try a lower kitten heel instead. You can also try a thicker heel such as a Louis or a stacked Cuban - the latter look better in boots than shoes.
Kitten heel. The kitten heel is a small stiletto or Louis heel about an inch or so high. Very useful on delicate shoes for women who don't feel comfortable in higher heels, but check your back view - a teeny tiny heel on a woman with a large backside looks terrible. If you have a large rear, choose a Cuban or Louis heel instead.
Louis heel (above right). A waisted heel from the 18th century that moves in and out of fashion. A Louis heel can be useful in a high heel because it's visually light but gives you more contact with the ground than a stiletto. It's usually combined with a pointed toe box.
Wedge. A heel where the heel is continuous with the sole, which lends more stability to the bottom of the shoe. A really good option for women who aren't comfortable in conventional high heels, and also useful in a foul-weather fashion boot. Avoid huge platform soles with wedges - this is extreme and ugly footwear that does no-one any favours - and choose, where you can, a wedge that is waisted towards the arch of the foot.
Cuban heel. Originally a boot heel and sometimes still seen on both boots and shoes, a Cuban heel is a solid, tapered heel. A classic heel for riding boots, including cowboy boots, as you can tuck it into the stirrups.
Court shoe. The classic court shoe has a narrow heel 1-3 inches high and a toe box varying from almond to pointed - de rigeur for businesswear in a dark leather such as black, brown or blue. I'd recommend buying a couple of good pairs each year and wearing them into the ground rather than having lots of different ones. Leather is easier to care for than suede, and kid leather is the most comfortable if you have the cash, but there are also companies that do cheap knock-off leather-looks such as M&S. If the tip of the toe box is cut away, the shoe becomes a peep-toe, and is a useful option for women who don't feel comfortable in sandals. For maximum sexiness in a court shoe, choose a cut-away vamp (that's the top part of the shoe) that exposes some toe cleavage.
Slingback. The classic slingback shape is the Chanel pump with with nude body coupled with a practical dark toe. However, the slingback comes in many different toe shapes from almond to pointed. Slingbacks are a very feminine option, but the back strap often lengthens with wear. If this happens, take your shoes to a cobbler, as it's an easy job to have the excess trimmed.
Mules. A mule is a backless slipper (in that you slip it on and off), which may have a heel of any height. high-heeled mules are considered to be very sexy shoes but are difficult to walk in and is best kept for at-home parties, or for going out if you've got transport. A flat, backless sandal in a mule style can be a useful summer shoe if you're prone to blisters, as there's no structure for your heels to rub against.
Escarpins. Shoes with very long, pointed toes, based on a medieval design. These have been back in fashion the past few years, in flat designs as well as heeled. The flat versions give a sexy alternative to ballet flats, but can be difficult to walk in if they're completely flat - try a kitten heel to give you some purchase. If the heel is higher, it's usually a stiletto or Louis to balance the pointed toe box.
Strappy shoes. IE: shoes held on by straps around the ankle. For under trousers, the straps can be relatively thick and supportive, but if you're wearing a skirt, stick to thin, delicate straps, as heavy straps will cut you off visually at the ankle and look very clumpy.
Ballet flat. The classic ballet flat is based on the ballet slipper - a shoe which itself is very difficult to wear because of its inflexible and narrow sole. Fashion ballet flats usually have a fuller sole and a small heel. Ballet flats are a good option for tall women with large feet, but if you have small feet they can look like a pig's trotter - instead opt for a pointy-toed shoe such as an escarpin with a kitten heel.
Brogue. The brogue is based on, and named after, an Irish shoe of the 18th century and earlier. Original brogues were designed for walking in peat bogs, and the pierced holes allowed water to run out rather than collect inside the shoe. Now, however, the holes are purely decorative and there is a leather underlay under the pierced top layer. Brogues do up with laces and are practical flat footwear to wear with trousers, particularly in the countryside, in which case the colour is normally some shade of brown. However, brogue styling (pierced leather and laces) can also be found in boots, court shoes and ankle boots.
Oxford. A flat lace-up shoe without the pierced leather detailing of a brogue. Oxfords are classic men's shoes and lend a similar butch practicality to a woman's wardrobe - best in dark leathers such as black and oxblood for wear with trousers or jeans. Like brogues, Oxfords also make the transition to heeled shoes and boots, especially ankle boots - the telling detail is the lace-up front.
Mocassin. The mocassin is a slip-on shoe worn by Native Americans. The originals were soft-soled and made from buckskin, but modern versions are usually made from suede or sometimes leather. A mocassin is characterised by its construction - the sole wraps right around the foot and is fastened to the tongue of the shoe, with raw edges and all stitching visible. Modern versions, however, also have an extra plastic sole attached to the bottom. Fashion mocassins are good everyday shoes for wear with trousers, and often feature as designs for slippers because they are very comfortable: they are occasionally available as boots, where they result in a very ethnic look. Don't go too far with that or it looks like fancy dress.
Loafer. The loafer is a modified mocassin without the raw edges and visible stitching. The loafer is a very practical walking shoe and a useful option for under trousers, but looks very frumpy with a skirt.
Trainer. The trainer, or sneaker if you're American, is based on a sports shoe design. Supportive at the ankle and usually featuring high-tech soles that cushion your weight, they are now ubiquitous wear under jeans and casual trousers such as chinos. The attraction of trainers is not how they look (unless you're a label freak) but the fact that they are extremely comfortable - the reason some New Yorkers wear them outside the office, only changing to court shoes once they reach work. If you favour wearing trainers outside the gym, look for ones in dark colours that mimic a conventional shoe and don't make your feet look enormous. For sports activities, buy the best you can afford and discard them annually before the soles deteriorate.
Pump. This word denotes two kinds of shoe - one, a slip-on or lace-up sports shoe (also known as a plimpsoll) in rubber and canvas, the other a low-heeled or flat court shoe, usually in leather. The former are useful and cheap summer shoes to wear with trousers, summer skirts or shorts, while the latter, popularised by Diana, Princess of Wales, are a good option for tall women who don't want to wear heels. What Americans call pumps the British would often call court shoes.
Espadrille. A cheap, near-disposable slip-on shoe with a sole made from coiled string and an upper made from canvas. They may be flat, or have a heel (usually in a wedge). Espadrilles are a comfortable, casual summer option for the beach, holiday and lounging about in the garden, but don't usually survive more than one season. Buy, use and discard.
Sandal. Sandals come in many designs, including 'Jesus' sandals and 'Scholl's', but the word is usually taken to mean open, strappy shoes with a flat sole (increase the heel height and a sandal becomes a shoe). Flat sandals are useful in summer for casual situations but are not suitable for businesswear - wear a good leather court or peep-toe shoe instead. Wear your sandals with bare feet - if you like to wear socks, choose a loafer instead.
Riding boot. The classic riding boot is based on British Victorian male sportswear and has a flat sole, small heel of up to an inch, and pulls on over the leg. They usually come in brown or black, or black with a chestnut top and the good ones are in leather. Traditionally they were polished with a piece of bone to bring them to a high shine. The riding boot is a very useful boot for both country and city wear, and a stylish foul-weather option for getting to and from the office. The majority of fashion boots are roughly based on the riding boot, with the addition of higher heels and sometimes a zip running up the inside leg.
Ankle boot. A useful boot to pop on when you don't want a full-length boot, the ankle boot works well with jeans and trousers but is best avoided with skirts. If you do like to wear your ankle boots with skirts, stick to monochrome or tonal schemes such as black skirt, black thick tights, black boots, and make the boot leg as long as possible.
Wellington boot. Based on the boot popularised by the Duke of Wellington, this waterproof, pull-on rubber boot is designed for maximum protection in foul weather. Modern fashion wellies come in plain black or a range of fun prints and are usually pretty cheap, while real wellies are more expensive, are usually in shades of green and may have very sturdy, non-slip soles and heels, and linings in materials such as neoprene or leather. If you live in the countryside, real wellies such as those made by Aigle or Hunter, are invaluable, but fashion wellies are a good buy if you have to negotiate city streets in winter. Choose fun ones - they're never going to look stylish anyway.
Cowboy boot. This tooled leather boot - the starting point for many types of fashion boot - is based on the footwear of US cattle herders and is characterised by a degree of intricacy and a Cuban heel. The original colour was probably a mid-tan or rust, but cowboy boots now come in every colour under the sun. The leather may be plain or figured, and the boot may have fringing up the back or sides. Many cowboy boots are slightly cut away behind the calf, so they don't cut into the back of your knee when you sit down, and they are generally shorter than the English riding boot. They also often zip, rather than pulling on, though both styles are available. Cowboy boots always, always carry a western flavour with them, and the usual accompaniment is jeans, tucked in, though they can also be worn with a long skirt. Keep the details classy and subdued for the best look, and avoid fringing, pompoms and whatnot.
Uggs. Uggs are now so ubiquitous that I'll make a case for them being a classic. These thick, sheepskin-lined, soft boots originated in Australia. Uggs have a flat sole and only marginally raised heel, thick treads and come in a wide range of plain colours. Good as an indoor/outdoor boot if correctly waterproofed, but they won't stand up to immersion or really filthy weather. As slippers they're perfect and keep your ankles warm. Uggs come in a range of leg lengths from bootees to knee-length.