How To Dress Well

How to dress for your first day in a new job

A foolproof guide to bossing it in your new office
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It was Tom Ford who famously said "dressing well is a form of good manners". Never is this statement more true than on the first day in a new job. Opinions are formed and judgements are made in those essential few moments when you first walk into a new office, and as important as a sharp haircut, a non-sociopathic smile or a firm (but not too firm) handshake may be, it's the outfit you choose to wear that will really make the difference.

So here, on my first day on the job as the new Style And Grooming Director of GQ (pray for me and my many shades of navy: see point 2), is my guide to getting your first day look on point, whatever the office or role.

1) The start-up

This really depends on whether it’s your start-up or somebody else’s. If it’s the latter: a pair of wide-leg Craig Green Core Collection chinos, some Converse high-tops, an artfully untucked Oxford shirt from JW Anderson x Uniqlo and a knitted-by-nanas crew neck sweater should do the trick. If it’s the former: your pants.

2) The established media hive

Tricky this (due to the fact that I’m now a worker bee in the world’s most established and respected media hive), but personally I would recommend keeping things simple. As a keen advocate of navy blue and clothes which fit, I’d opt for a simple Bengal striped shirt (collarless or collared: your call), a pair of slim, single-pleat charcoal trousers with a turn-up and a fine gauge cashmere sweater in navy.

A pair of desert boots (Prada, ideally), some socks in a slightly lighter or darker shade of grey than your trousers and a midnight-blue blazer with a pattern that contrasts subtly to the shirt will also work wonders. The key here is to make sure the shades of blue are complementary; too much yellow in one and too much red in the other has the potential to ruin everything. Check your outfit in daylight before you leave to avoid disasters.

3) The financial behemoth and/or magical circle law firm: entry level

Ignore the fact that JP Morgan, Price Waterhouse Coopers and the House Of Commons have all decreed that employees/members need not encumber themselves with ties and jackets. On your first day in a serious financial, legal or political role (particularly one where you’ll be representing your company externally) you must wear an impeccably cut suit, a sharply ironed shirt and a perfectly tied neck tie. It doesn’t matter which level you’re entering the business at – junior clerk or senior analyst, legal secretary or barrister – you must dress appropriately for the role.

For those at the shallower end of the budgetary pool, I would advise heading to J Crew, where you should buy a single-breasted Ludlow suit in a dark shade before getting it cut to fit (by fit I mean that it should frame your frame, rather than cling to it) by a tailor. Team the suit with a white cotton shirt (not a button-down or shudders "muscle fit") and a tie in a lighter shade than your suit. The simpler your outfit, the more elegant it will look. Shoe-wise, opt for a pair of black lace-up Oxfords from Grenson or Crockett & Jones.

4) The financial behemoth and/or magical circle law firm: high roller

If you have more cash to spend, head to Anderson & Sheppard, Richard James or Gieves & Hawkes on Savile Row and have a made-to-measure or bespoke suit cut to your frame. Team with a white collared shirt (save colour and pattern for later, when you’ve established yourself), a pair of deep-brown Oxfords from Berluti or Gaziano & Girling and a pair of perfectly round tortoiseshell glasses from EB Meyrowitz. Nothing says "I'm just an unassuming master of the universe, how about you?" like a pair of eye-wateringly expensive tortoiseshell glasses.

5) Anything outdoorsy

This is quite a broad one, but the key to working outdoors is to come prepared. The main thing to remember is that you should wear items of clothing which are actually designed to do the job, rather than ones which merely look like they are (your colleagues will be able to tell the difference). A pair of Redwing or Timberland boots (functional ones like the Pro range from the latter, or the DynaForce range from the former) will last an entire career if cared for properly. Clothing-wise, a pair of heavy-duty selvedge jeans from Levi's will go on forever (there's a reason why denim was originally used to make miners' overalls), likewise an oiled tin cloth jacket from heritage brand Filson will keep you both warm and dry at a surprisingly reasonable price (around £250).

6) The barista job in a bike shop

Anything but a beard.

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