How to be dapper but not a dandy, what to wear to a beach wedding and how many times can you get away with that jacket?.

OK, we’re in a rhythm now, so you know how this works: each week we invite you to submit your style-related questions via your chosen medium of communication. We collate them, discuss them internally, then each Friday select a few to answer.

This week we deal with the issue of how often you can get away with wearing the same outfit and what you can do mix and match your wardrobe in order to freshen things up. Plus, we deal with the fine line between dapper and dandy; lastly, we offer some practical advice on what to wear to a beach wedding.

Keep your questions coming.

Is there some hidden rule that you shouldn’t wear the same outfit within a certain time frame, or does it really not matter? I try to mix and match my outfits but I’m running out of ideas.

From lifebyzach, via Instagram

There’s no rule about this kind of thing unless you’re a celebrity who appears in gossip magazines, in which case repeating an outfit is a heinous crime punishable by catty picture captions.

The truth is, we all tend to fall back on tried-and-tested favourites, whether it’s a signature dinner-party dish or a winning outfit. There’s nothing wrong with that, per se, but you can overdo something, particularly if it’s a standout piece. Wear a snazzy jacket once, people will notice. Wear it twice, people might think, “Oh, he’s wearing his snazzy jacket again.” Wear it three times in as many weeks and suddenly you’re “Snazzy Jacket Guy”.

So here’s an idea when you’re running out of your own: use MR PORTER for instant inspiration. Say, for example, you’re looking for different ways to mix and match your denim shirt. Type “denim shirt” into the search box on the home page and it will throw up a sizeable number of different options – 72 at the time of writing. Hover over each option and you’ll see 72 different but successful ways of wearing such a shirt, at least some of which you’ll be able to approximate using similar items you already own. This way you can freshen up your look without having to buy loads more stuff. Though naturally, our employers would probably like us to point out that buying loads more stuff is also definitely an option.

How do I wear Italian tailoring (soft shoulders, light colours, etc) without looking like a dandy?

From theraging_bull, via Instagram

It’s interesting how the word “dandy”, like “hipster”, has gone from being a compliment to a pejorative descriptor in recent years. A dandy used to be seen as dapper, now it connotes a try-hard.

I have a similar issue when it comes to hats. I quite like the idea of them, I often like how they look on other people, but whenever I try one on it seems a bit “fancy dress”, like the hat is wearing me rather than me wearing the hat.

On the one hand, it’s a question of comfort and confidence level, and sometimes you just need to be bold and give it a go. As the Dr Pepper tagline used to run: “Try it, you might like it.” But it’s also about styling. Just because you’re wearing Italian tailoring doesn’t mean you need to dress like a Pitti Peacock. The important thing is to keep the rest of your outfit pretty low-key and casual. A dandy tends to throw everything into an outfit and overdo the accessories: bracelets, pocket square, lapel pin, sunglasses, sockless loafers – and yes, a hat.

My suggestion would be to dial it right down and either wear a plain collared shirt or a simple T-shirt with the tailoring. Wear with minimalist, clean, white tennis shoes. Limit yourself to one or two accessories only.

What’s appropriate to wear for a beach wedding?

From Adam J, via email

Test-drive your outfit first. Linen tends to rumple too easily, especially if it's been folded in a suitcase, so I’d suggest a seersucker suit such as this one from Officine Generale, which won’t crease. Or chinos with an unlined jacket. Definitely a white shirt – pastels show up sweat. Wash it beforehand: packet chemicals can be scratchy and give off an unpleasant smell. Take a tie (plain navy) for the photos. Leather sandals are far preferable to flip-flops on the beach. The man from Del Monte, he say “yes”.