The best men's smart casual chukka boots

Last week I did a webinar for some members of the Hayley Quinn Dating Academy. After discussing smart casual shoes with a couple of the guys who took part, I decided the most versatile and stylish shoes would be a pair of chukka boots. They both had completely different styles and wouldn't go for the same pair but either way they can go with jeans, chinos and some of the more formal ones look good with tailored trousers too.

If you don't have many smart casual shoes in your wardrobe (a frequent gap I find when I do wardrobe edits) then perhaps you'll find something you like in the suggestions below:

James Purdey Sons suede chukka boots - personal stylist for men

Wear these brown suede chukka boots for a smart dinner date with a pair of tailored navy chinos, a pale blue shirt and a grey blazer, or with a pair of jeans and a field jacket as they've styled them on the Mr Porter site, for a second date walk in the park.

Brown suede chukka boots - James Purdey & Sons at Mr Porter - £425

Drakes James Bond chukka boots - personal stylist for men in London

One of the questions on the questionnaire I send out ahead of a personal styling or shopping session, is "Is there a particular public figure or celebrity who's style you admire?" It doesn't always get answered, but when it does, the name Bond......James Bond, often crops up!

And guess what, you're in luck because these chukka boots are the exact ones (in chocolate brown) that Daniel Craig will be wearing in the upcoming No Time To Die. Unfortunately the film's been postponed till November, but you can get ahead of the game and get a slice of Bond style right now!

'Crosby' moc toe tobacco suede chukka boots - Drakes - £275

Oliver Sweeney brown leather chukka boots - styling advice for men

If you prefer leather to suede, then these classic dark brown chukkas from Oliver Sweeney will be the ones for you. Wear them to work, wear them on a date, wear them to the pub, wear them in summer, wear them in winter. They'll become a staple that you'll wonder how you ever lived without.

'Farleton' brown leather chukka boots - Oliver Sweeney at John Lewis - £169

Paul Smith navy suede chukka boots - personal styling for men

Already have tons of brown and tan shoes and looking for a change? Navy is a great colour for Spring / Summer with lighter coloured trousers, such as mid to pale denim, ice grey chinos, or soft khaki 5 pocket jeans. Once we get further into summer, wear with one of the many pairs or white or off white jeans that are around and a navy shirt or try out this look with a chambray shirt and sweater.

'Arni' dark navy suede chukka boots - PS by Paul Smith - £225

Grenson black leather chukka boots - personal shopping for men

Prefer to go for a sleek and classic look? Then black chukka boots are your answer. I find them a little more versatile than chelsea boots as they'll look great with some slim black washed jeans and a leather biker jacket, but will also look good with a dark navy cotton suit and crisp white shirt for an evening out to a smart bar.

'Wendell' black leather chukka boots - Grenson - £255

Struggling to get your smart/casual wardrobe together? Drop me a line here to book in a shopping trip and get your wardrobe sorted asap:

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