Ask a Stylist: can I wear shorts to work?

I like the idea of smart shorts in the city, but I’m not sure how or even if I should wear them? I also like the idea of shorts suits

Ah, the smart short. Casual ones are oh so easy — denim cut-offs for beach days and picnics, soft towelling or silk for lounging, and cotton boxers for pretty much anything else. But as is often the case, once we need to make something into a smart casual outfit, we are flummoxed.

Shorts can seem challenging but they offer a relaxed ease when done well, so it really is worth trying. Plus, it is always good to give your look a bit of a shake-up every now and then.

Let us address the length straight away. People often assume you need to go longer for something to be flattering but this is not always the case. In fact, with shorts (the hint is in the name) it is often better to go slightly higher. I am not advising that you rock up to the office in a hot pant but do try rolling up once, or even twice, to see if the short looks better. My guide is to look for that sweet spot on the leg where it starts to narrow.

A great way to check this is the “towel trick”. Stand bare-legged in front of a full-length mirror (if you don’t have one — get one!). Hold a bath towel in front of you from hip to toe then slowly raise the towel up to reveal your legs. Look at the area around the knee: where is the narrowest part? For most of us it is just below the knee, for some it is bang in the middle of the kneecap and for others it is just above. Next, check between the knee and the upper thigh. Again, where is the narrowest part? Remember this spot so that you know exactly where your shorts should sit when you are shopping. 

Bermuda shorts (the longest version of a short before you get into dangerous Capri pant territory) are traditionally knee-length and tend to work best on taller, longer-legged women. These can look incredible for the office, assuming your work would not frown at a tailored short. Once you have ascertained if they are for you, ignore any paper-bag waists or excess pocketing. Pleats can work, just check that they don’t balloon out when you look at yourself side-on. The beauty here is in the simple silhouette. 

Tommy Hilfiger’s white version (£91 on sale, uk.tommy.com) is crying out for a clean black T-shirt, silky black vest or dark shirt. You could even try a sporty V-neck knit — Margaret Howell’s collaboration with Fred Perry is just the ticket (£135, margarethowell.co.uk). You could wear it with or without the matching jacket on top (£189 on sale, uk.tommy.com). I would add a heeled sandal like Soeur’s classic brown look (£235, soeur.co.uk). Or you could choose a slingback with attitude, such as this furry pair from Acne Studios (£294 on sale, acnestudios.com).

If you are curvy, look for a softer fabric. Try Vince lyocell (this fabric is absolutely magic in the heat, by the way) shorts in caramel (£325, vince.com). I’d add Tibi’s smart polo top (£375, net-a-porter.com) and a sandal or court shoe. 

Now, shorts suits. You cannot dispute that the Duchess of Sussex does tailoring awfully well, especially when it comes to a shorts suit. She wore a delicious pink version in April for a baseball game, and a billowy white pair for a polo match in May in 2022. And who can forget Julia Roberts in that brick-red shorts suit in Pretty Woman? It is etched into my fashion memory — so smart yet feminine, so pretty yet powerful. That is the look I am after.

Don’t be scared by a shorts suit — it is the obvious alternative to a trouser or a skirt suit in summer. In fact, you could argue that it is infinitely easier than a skirt suit, as you run less risk of flashing too much thigh.

Max Mara’s linen suit is very easy. It comes in pink, ivory and yellow (shorts, £140 on sale, gb.maxmara.com, and blazer, £256 on sale, gb.maxmara.com). If you cannot face the whole suit, you could wear the shorts with a navy jacket shirt or simple tee instead. Gant has a great stretch linen classic suit in navy — comfortable and cool (shorts, £140, gant.co.uk). Pop on a white tee and a sandal and you’re good to go (£55, gant.co.uk). 

If you want something a bit more “fashion”, then choose Raey’s pitch-perfect oatmeal style. Size down if you don’t want it loose (shorts, £295, matchesfashion.com, and jacket, £595, matchesfashion.com). Imagine how beautiful any of these suits would be for a wedding or dressed up with statement heels and jewellery for an evening out.

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