Away from the office
You may be a Mad Man in the office, but if you become Slob Man as soon as you step out if it you'll ruin the effect. Always look put together - without looking like you've tried too hard - whether at the tennis club, the races or the bar.
First things first. Don Draper doesn't on any account walk around with the tops of his boxer shorts showing. Go for trousers - slim fit flat fronted cotton trousers or chinos rather than jeans - with a slightly higher rise than you may be used to.
After that, polo shirts are as "now", er, now, as they were then. Sleeveless sweaters are classically preppy, and you should probably invest in a fine knit cardigan or shawl collared jumper.
"Plaid trousers or jackets will also look good - a check Harrington style jacket or plain for a more conservative look, or a check cotton blazer," says Gilfillan. "Coming into winter, look for a wool version - this can just as easily be worn with your jeans if you don't want to go for the whole look."