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How To Style a "Tricky" Item
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How To Style a "Tricky" Item

Tips on styling that unusual piece you love.

Angharad Jones's avatar
Angharad Jones
Apr 10, 2025
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How To Style a "Tricky" Item
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Do you ever see — or try on — an item of clothing and think: “I love it but… how would I wear it?”

I posted a vest on Instagram last week and that exact question came flooding into my DMs. I asked subscribers in my chat here on Substack what they thought about vests, and there were responses along the same lines. Often, we have one “go-to” way of wearing something, especially if it’s more of an unusual piece, and we stick with what we know.

But if you’re trying to build a considered and long-lasting wardrobe, it can be hard to own (or justify buying) a piece that doesn’t get as much wear as you would like. And we’ve all had that sinking feeling when we spot said piece gathering dust.

So here are five ways I’ll be wearing the vest over spring and summer. Plus, there are a few styling “hacks” for coming up with different outfits (with little effort involved).

The vest in question*. Worn here with Tillsworth shirt, Monokel ‘Ellis’ sunglasses (use code angharad for 10% off site-wide), Toast trousers* (I wear size 6 but my ‘usual’ size in other brands is 8)

A close-up of the vest. It’s soft black cotton with a machine-stitched graphic stripe across the main body and hems that are hand-Kantha-stitched by artisans in India. It’s slightly longer at the back than it is at the front and there are two ties on each side that can be worn loose or tied. I wear this vest in a size S.

Look 1

Wearing: Toast vest*, Organic Basics top* (in size XS), COS trousers (old. Similar here), Uniqlo leggings, Zara Mary Janes (old. Similar here), Shape of Sound ring*

Whenever I struggle to come up with outfit ideas, I think about combinations that I love to wear and go from there. Wearing leggings under cropped trousers is one of my favourite ways to layer and it creates a really interesting silhouette, so I knew it would complement the unusual shape of the vest.

These trousers have a high waist so even though the vest is cropped, it fits neatly over the waistband, meaning I don’t need much underneath to cover up. I have a cropped top meets yoga bra from Organic Basics that I’ve worn underneath. It’s quite thick cotton so it makes a nice layer, it provides more skin coverage than a regular bra and it still gives me the support I need.

Look 2

Wearing: Toast jacket (last season), Toast vest*, Tillsworth shirt*, Monokel ‘Ellis’ sunglasses* (use code angharad for 10% off site-wide), Toast trousers* (I wear size 6 but my ‘usual’ size in other brands is 8), Zara Mary Janes (old. Similar here)

Days have been warm in the UK recently, so I’ve been layering with light pieces that can be shed or built on, depending on the temperature (something I wrote about more in my spring outfit formulas post).

A vest like this one is the perfect layer for this kind of temperature (17°C and sunny, if you’re wondering). It acts like a shield to cool breezes when you’re wearing something light, like the button-up shirt I have on here, but it isn’t too warm or bulky, so you can slot it under light jackets too.

If you’re ever unsure about how to style an item, look at its colour(s) and start from there. Here, I’ve picked out the black and white of the vest and reflected them in the shirt, trousers and flats. The sand-coloured jacket adds a softness and a break from the monochrome but it’s still a neutral colour so it doesn’t distract from the very classic colour combination.


The rest of this post is for paid subscribers. Behind the paywall, you’ll find ways to wear the vest with dresses, more colour combinations, and more ways to layer.


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