Of the many style conundrums I get asked to solve, possibly the most popular besides, ‘which pair of black trousers won’t make my bottom resemble Kim Kardashian’s’, is what on earth to wear to a wedding or Ascot?

It’s not the British way to attend a Big Day Out in a sensible dress and mid-height heels. The catwalks may be awash with midi-skirts, comfy looking brogues and slim, prim skirt suits but on Planet Corporate Hospitality or a marquee sitting in a water-logged field, it’s a moot point how open to interpretation the modest “ day dress” code has become in recent years. If ever there was a lesson to be learnt from Ascots past  – when outfits reached such a low that the Duke of Devonshire was hauled in by the Queen to remind race-goers that knickers must be worn yet not seen – it’s surely not to trowel on more but go for the make-under.

Also, if you’ve already had to fork out for the hen “festivities” aka spending several hundreds of pounds for the privilege of wearing L-plates and falling into a Brighton gutter, you will understandably want to invest wisely when you attend the wedding.

Because one of the trickiest aspects of dressing for summer occasions is marrying your own style (yup, what you actually like to wear the rest of the year) with the floaty florals and saccharine pastels in easily combustible faux chiffon fabrics or the Dynasty style tailoring that women think they are expected to wear.

If you’ve always worn neutrals and your wardrobe could teach a polished, “no carbs, no dairy” New Yorker a thing or two about minimalism, then why are you thinking about a pink swirly hat and full-skirt, Fifties ensemble. Remember: looking elegant and appropriate needn’t mean looking like a frump. I say this because can there be anything more ageing than a boxy cut shift dress and matching frock coat? This familiar outfit (worn up and down the land come June) which references the Sixties tries to channel Jackie O but fails miserably. And yet for many women who mistake classic and appropriate for boring and dowdy, this dress ensemble has become the outfit of choice. Never mind that a waist ravaged by childbirth could do with a little help and definition.

The good news is that in fashionable circles these days, less is also very much more. And not looking as you’ve tried too hard is a good enough mantra to incorporate when setting off: it doesn’t mean you haven’t tried at all but that your efforts should be worn lightly. And the best way to effect this is to wear souped- up versions of the kind of clothes you feel most comfortable in.

For some women, not wearing the conventional building blocks of the “expected” formal uniform, or at least mixing them unconventionally, is key to retaining a sense of self. The mismatching jacket and skirt combo is probably a good place to start: pretty chiffon peeping out from beneath a fine-knit cardigan or a less structured jacket looks more modern than wearing a suit. Colourwise you could go for some tonal layering and mix up the prints to create take a leaf out of Jenna Lyon’s book, the creative director of J. Crew. Alternatively another way to create impact without resorting to an overload of pattern is to explore interesting textures such as embellished,jewelled applique or a chunkier weave fabric. Block colours are another way of contouring the body creating the illusion of height and slimming the waistline. Lace has been a big daywear trend for a couple of years now but it only looks good if it is good quality lace – of the thick, crunchy variety which can be tailored, which adds warmth and coverage and yet still looks light.

Personally I love monochrome, it looks crisp and sharp although instead of going 50/50, allow one shade to dominate. I’m also a fan of the tea dress. It’s a classic and for good reason: it works. Otherwise try the full skirt – find plenty of them at LK Bennett. Great places to look for any of the above are also Cedric Charlier, Jaeger , avenue32.com and Suzannah.com.

When it comes to covering up, the wrong cardigan or jacket– ie one that doesn’t work with the flow of the dress – can kill an outfit. It’s worth taking all of this into consideration when you are deciding what to wear. As a general rule cropped jackets are best with fitted dresses while blazers look better with tea dresses. And while pashminas and shawls are certainly useful, draped around the figure-hugging dress that you’ve gone to a lot of effort to get (and get into) is tantamount to swaddling yourself in a giant curtain.

Also, it’s crucial to work out how much of the day will be spent on your feet. Are the towering hooker sandals, really such a great idea? If you are wearing a wedge heel then consider choosing a formal pair rather than a raffia, espadrille style more suitable for the beach. Stilettos are wholly impractical on grassy surfaces. And stay committed. Emma Thompson just about got away with it at the Golden Globes. Chances are you won’t. Finally a word on accessories: a hat plus watch, clutch and rings, bracelets and earings and necklace equals Christmas tree. Choose wisely. Choose sparingly.

Some thoughts on hats:

Possibly I am in the minority when I tell you that I feel like a rice paddy worker when wearing an occasion wear hat but for anyone else who dreads picking a hat to wear to a wedding or Ascot they might want to get themselves down to Fenwick pronto. Not only does it do the best assortment of hats (favourites include those by Jane Taylor, Noel Stewart, Piers Atkins, William Chambers).

If you’re stumped on the outfit, then it’s also worth booking in with one of the store’s personal shoppers (such as Carolyn Lagenhoff) who offer excellent advice in what is certainly the most pleasant retail environment in London.

If you are looking elsewhere, John Lewis, Selfridges and Edwina Ibbotson are good, but how best to find a hat that complements your face?

In my experience (and many years having to report from Ascot) round faces suit soft crowns and brims in loosely woven straw or soft fabrics, while square or rectangular faces suit flatter crowns and straight brims in crisper, finer straw or lightweight felt. “Asymmetric,” is flattering on most people, and a straight or upturned brim gives your face a bit of a lift.

To accentuate cheekbones: wear an asymmetric form worn across one eye. If you’re very petite: the number one rule is to wear a hat in proportion to you. Another trick is to go for a hat with an asymmetric brim that draws the eye up when you look at the wearer. Also a brim that goes up on one side. For small heads: go for a hat that perches quite high on the head (like a pill box) or a small headpiece. Normal crowns and brims will swamp the wearer. While pill box style hats suit shorter hair.

It’s worth noting that at Ascot the dress code stipulates that fascinators are no longer permitted (no bad thing this as they often look as if a bird has just died on your head) and that the base of the hat’s headpiece should be a minimum of 4 inches in diameter.

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