Gather round, my friends. My years spent overthinking clothes have been rewarded with a few nuggets of genuinely useful wisdom, and I am about to share one of them with you. Ready?

Here’s the thing. When your desire to wear an item of clothing is driven by wanting to look the way one specific person looks in that item of clothing – and that one specific person looks nothing like you – stop right there. Take a step back from the checkout. Close down the online shopping tab. It just doesn’t work.

You see, in an ideal world I would look like Jane Birkin in blue jeans and a white T-shirt. But I don’t look anything like Jane Birkin, and not even the perfect jeans nor the ultimate T-shirt will change that. Same goes for looking like Naomi Campbell in a bikini. The best swimwear in the world will get me precisely nowhere on that front. See?

Anyway, I have this thing with dungarees. In the aforementioned ideal world, I would look like Alexa Chung in dungarees. With, like, a messy bob and cool trainers. So into that look. But I don’t look like Alexa Chung, and therefore I won’t look like Alexa Chung in dungarees, I will look like me in dungarees, which is less style-icon-playing-down-her-intimidating-beauty-in-utilitarian-workwear than fashion-editor-dressed-as-children’s-TV-presenter. So. No dungarees for me.

The good news for those of us who are not Alexa Chung, in or out of dungarees, is that pinafore dresses are now a thing. Pinafore dresses have the breezy, nonchalant aesthetic that I like about dungarees minus the vaguely comic crotch area and the terrifying back view.

However, even at my high level of enthusiasm, I don’t think the pinafore is a piece you are going to want to buy several of, so I suggest you look for one in a more grownup fabric than denim, and then you can wear it to work as well as at the weekend, without looking like you belong on the railroad. You want something weighty, so it doesn’t crease badly when you sit. Crepe or wool, maybe, or I am really rather taken with the Kitri dress I am wearing here. A pinafore works well with a smart silk blouse, or a fine-knit sweater. Sleeves to the elbow or longer will look more elegant than T-shirt-length or cap sleeves.

You know who you will look a tiny bit like? You. It suits you.

• Jess wears Pinafore dress, £115, kitristudio.com.Blouse, £175, bimbaylola.com. Heels, £49.50, marksandspencer.com. Jewellery, Jess’s own. Styling: Melanie Wilkinson. Hair and makeup: Claire Ray at Carol Hayes Management.