How to dress like Rory Stewart

    4 October 2019

    You can tell a lot about a gentleman from his choice of tie and the same is true of our politicians. If there’s one man from whom we can all pluck our seasonal flair, it’s Rory Stewart. He was one of my sartorial favourites from the leadership race and, as he prepares to throw his hat into the ring to become mayor of London, it’s time to take notes on his approach to winter dressing.

    Rory recently won politician of the year at the GQ awards – a plaudit made even more profound not because of the whip withdrawn that very day by the PM, nor the fantastic tartan double-breasted waistcoat and trousers, but because he was almost certainly the only person at the entire tuxedoed affair who wasn’t wearing a pre-tied bow tie. I wasn’t invited, obviously.

    The first time I came across Rory’s style inclinations, which are admittedly subtle, was during Ian Hislop’s documentary on the stiff upper lip. Rory spoke of how, during mortar attacks and riots, he placed high importance on putting on a well ironed white shirt and jacket every morning. Be still my beating heart.

    Since that time, Rory hasn’t exactly blazed a trail but he has done all the simple things well, which is enough for the ears of the sartorially-minded to prick up in curiosity. We can take the quotidian navy suit look for granted: generous lapels, perfect fitting over the shoulders and flattering shape at the sides. He also has a rather fun affectation of wearing shirts that are far too long for the jacket sleeve so the amount of cuff on show is substantial, a nuance that he has told me is not on purpose, but I don’t believe a word of it. It is his mufti that will be of most use to you for October. In absence of knowing exactly where he buys his clothes, I have taken artistic license to present a full, Autumnal Rory Stewart look.

    The coat

    Rory Stewart, Getty Images

    On his walking tour of the Conservative leadership race, pretending to record himself and being otherwise considered and reasonable, he wore a light, unstructured raincoat. These are becoming ever more popular especially for commuters, who would need to faint once they got onto the tube in wool overcoats or trendy (depending on your animal rights outlook) Canada Gooses. His had a raglan sleeve – where the sleeve ends at the neck rather than the shoulder – but that puts stress on any structured shoulder you may have on your jacket so this version from Hancock would work perfectly.

    The Jacket

    New & Lingwood country sports jacket

    A country sports jacket is his go to when door-knocking in Penrith, he can be found wearing a tweed sports coat with muscular check patterning. October is after all an important month for country sports, with the pheasant season starting, so there’s more than one excuse to stock up on a jacket like this one from New & Lingwood.

    The shirt

    In all fairness he has declared his fondness for white shirts, but I don’t think the countryside calls for one. If you insist in following in his footsteps, opt for a two-fold cotton, which is a little heavier and offers a bit more structure an insulation. Not to be a snob but somewhere like TM Lewin may not know quite how many folds their cotton has so go to a specialist shirt shop on Jermyn Street, Emma Willis or Hilditch and Key do really tremendous white shirts.

    If you want something really special, ask for cashmerello, a cashmere and cotton mix fabric that is luscious and comforting to wear. The aforementioned brands do stock these but from personal experience, the one I had made at Turnbull and Asser, with a pink base and light blue check, was a masterpiece and I can be confident you’ll be happy with them.


    The Barry tan antique, George Cleverley

    Rory likes his wellington boots, but his chukka boots are also a favourite and their well-worn patina gives away his affection for them. Chukka boots aren’t a personal favourite, a bit rugged and inelegant with my size 12s in them, if I were to choose a semi-boot it would be the Chelsea boot from Gaziano & Girling, which is unusually impressive as it is whole cut rather than two cuts of leather joined underneath the elastic. Wear with denim or heavy moleskin trousers.

    If you want to stick with the chukka then the Barry by George Cleverley is the thinking man’s version with a rather beautifully squared-off apron (stitching at the top of the upper).