“Effortless” is hardly the way to describe the search for footwear to  match    this season’s trousers and longer skirts. I discovered this  after trotting    off to Selfridges’s new gigantic shoe world (eight  rooms, 11 individual    branded boutiques, hundreds of shoes and boots  to try on), where I imagined    I’d be in danger of spending far more  than I ought. An hour and a half    later, I was back on Oxford Street,  empty-handed, fuming over the fact that    most footwear design hasn’t  yet caught up with the leading edge of fashion.
  All I gleaned from that wasted trip was the realisation that the  monstrous    platforms and rock-chick shoe-boots slavishly worn with the  short dresses    and leggings of the past few years are still endemic.  Just looking at them    makes me nauseous. Needless to say, they’re  wrong with this season’s    trousers and mid-calf skirts, which happens  to be all I want to wear.
  
               
The stacked-heeled ankle boot, £60
 Thrashing out what’s right has taken a hell of a time. This is due,  partly, I    admit, to the wrench it takes to break a fashion addiction  built up over    years: the plus side of elevated heels was feeling six  inches taller and    skinnier. When stepping into this season’s  anti-platform, non-statement    shoes, there’s that fear to conquer;  with these new silhouettes, frumpier    and dumpier must be  circumnavigated.
  Having scrutinised all the catwalk shows that featured trousers and  longer    skirts, I pulled out everything in my wardrobe that resembled  them, plus all    the shoes I’ve accumulated over 10 years. And now I  have conclusions: when    you whittle it down, there are two types of  footwear necessary to make this    season’s clothes viable – a pair of  pointy stilettoes and some sort of    block-heeled boots.
 Trousers are the tricky part, because they come in three shapes: 
 1) Wide-legged. Footwear appears not to matter with  these pants,    because the point is that the hem covers the shoe, thus  making it invisible,    except when walking. That means you can take  advantage of the old Seventies    leg-lengthening illusion: high,  stack-heeled boots or platforms, but    roundish or squared in the toe,  not pointed. You could also wear socks with    an old pair of chunky  sandals – the point is to cover and de-emphasise    foot-awareness.  (Study: 3.1 Phillip Lim, Marc Jacobs, Dries Van Noten.)
 2) Boot-cut. This Nineties’ revival takes finessing.  It needs    streamlined, narrow-heeled boots with a slightly pointed  toe, probably in    suede. Frida Giannini at Gucci styled her revived  boot-legs with open-toed    sandals and black tights. (Study: Balmain,  Gucci.)
 3) Narrow-leg, cropped. For women who’ve been living  in leggings, these    slim trousers might seem the easiest segue into a  new look. The key is to    ditch those grotesque “statement” shoes and  invest in pointed stilettos to    wear to reveal chicly bared ankles.  The most versatile and flattering height    is around three inches, the  über-ideal being a pair of Manolo Blahnik’s    timeless spindly-heeled  suede courts. Alternatively, there’s the rockabilly    way to do it, as  exemplified by Isabel Marant’s Fifties pointed courts with    cropped  jeans – how right they are is testified by the fact that they sold     out by mid-August. (Study: Stella McCartney, Gucci, Isabel Marant.)
 What to wear with new-length skirts: 
 1) The Fifties-look circle. The obvious companion  for the belled,    petticoated skirt is the “petite stiletto” or a  1.5-inch Louis heel with a    point decorated with a bow. At the  designer end, Tabitha Simmons and    Giambattista Valli have  mouth-watering evening options, and at the other,    Marks & Spencer  has a £15 patent version and New Look, one by Giles    Deacon at  £24.99. Close study of the Louis Vuitton pumps shows they, in    fact,  have a high- stacked heel rather than a stiletto. (Study: Prada, Louis     Vuitton, Dries Van Noten.)
 2) Below-knee A-line. A skirt with which both the  pointed stiletto and    the block-heeled boot work, thus side-stepping  the frump issue. There are    subtle differences within A-line, though.  As a rule of thumb, if it’s    bias-cut, sinuous, tending towards the  Thirties, wear the stiletto. If it’s    stiff and skewing Seventies, use  the chunky-heeled boots.