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I spent it all on clothes by the looks of things...

Six casual trouser-based outfit ideas

I was going to do shorts this week, but literally every time I write about what I think might be ‘weather-appropriate’ clothing for the days ahead, the heavens opens and the clouds roll in. So I’ve decided to play it safe with six casual trouser-based outfit ideas instead. Maybe this means there’s a heatwave on the way. We can but live in hope.

I’d like to take this opportunity to welcome some new readers to the group. Last week’s post was quite popular, so I hope some people have returned for this one. Just to bring you up to speed, here’s a little bit about this blog and how it came about. I started writing it almost six years ago, mainly just to share my love of fashion and putting outfits together. Back then, I said that I wouldn’t feature anything that I wouldn’t wear myself, and that remains true to this day.

I’ve always loved fashion, ever since I was a small child. I still remember pestering my mother to get me those suede pixie boots from Dolcis for my 9th birthday, and that ribbon-trimmed ra-ra skirt from Chelsea Girl to go with them. As soon as I had my own money, I basically spent it all on clothes (hence the name ‘Wears My Money’). I only got a paper round because I saw a white jersey parka jacket in Miss Selfridge that I wanted to buy. Obviously a white jersey parka jacket is completely impractical which meant my parents weren’t going to buy it for me, so I had to earn my own money.

Later on I went to London College of Fashion to study journalism and promotion but ended up getting a work experience role at a music PR firm. £50 a week actually felt like a lot in 1994. From there, I fell into a full-time role doing radio promotions at a small music PR company in an office above a factory in Hayes (and they say the music business is glamorous). Four years at a heavy metal record label followed (this time above a warehouse in Acton), and I still have the tattoos to prove it, although they are slowly being lasered off now. 

In 1999 I got a job at EMI Records (later to become Warner Music) doing TV and radio promotions and I stayed there for 21 years, 21 years I tell you! When I started, I was a lithe 26-year-old wearing crop tops and Maharishi combat trousers. When I left in 2020 to go freelance, I was perimenopausal with two teenage children and a couple of extra chins.

Sorry, I didn’t mean this post to basically be my CV, but I know I always find it interesting to hear about people’s routes to where they are now. I started with a love of fashion and it’s come full circle. But enough about me, let’s get on with the outfits…


If Dorothy Gale were a modern-day, grown-up woman, living in a city in the UK, I feel she would be wearing this outfit. The heeled, glittery ruby slippers would have been replaced by more practical flats. The puff sleeves would remain in a more subtle form and she’d need a nice pair of chinos to wear while riding her bicycle.

casual trouser based outfits

1. & Other Stories printed frill blouse 

2. The Drop Addison soft volume handbag 

3. Whistles Ella denim patchwork jacket 

4. Arket linen blend barrel leg chinos

5. La Redoute leather ballet flats 


I’ve said it before and I’ll say it again, always check out the men’s department when looking for sweatshirts. Or knitwear, but sweatshirts in particular. There’s always more choice, better styles and, for me, they often fit better too. No one wants a slim-fit sweatshirt. I am a UK 12 and usually go for men’s medium when buying jumpers. Also, how cool is this weekend bag? 

casual trouser based outfits

1. H&M short sleeved linen blend shirt 

2. Maison Kitsune grey printed sweatshirt (on sale) 

3. Cos barrel leg mid waist jeans 

4. Free People New Horizons weekend bag 

5. Timberland Greenstride Ray city sandals 


Kirsten Dunst doing the wide leg high waist jeans in style

I’ve stolen this look again from Rose from ‘The Split’. Also inspired by Anne Hathaway’s character in ‘We Crashed’. Both fans of high-waisted, wide-leg jeans paired with a nice blouse. I bought these M&S jeans last week and they are just perfect. Add a cute tweed jacket and some gold accessories to make it a bit more on the smart-casual end of things.

casual trouser based outfits

1. Warehouse lace insert yoke detail top 

2. Matalan gold woven cloud clutch bag 

3. Mango tweed jacket with jewel buttons 

4. Per Una high waist wide leg jeans 

5. La Redoute plaited flat sandals 


Anine Bing showing casual sweatshirt style

Want to wear trousers that feel more like joggers? Then how about this linen pair from H&M. Would also look good with a white shirt and sandals on holiday or if the weather perks up over the next few weeks. 

casual trouser based outfits

1. Anine Bing Paris sweatshirt 

2. Whistles LF Markey puff sleeve jacket 

3. Sandro tan leather belt bag 

4. H&M linen joggers 

5. Vans Old Skool SK8 low trainers 


Excellent trousers from Finisterre

My friend Arlene literally dragged me into Finisterre to try these trousers on as she proclaimed them to be the best-fitting trousers ever. I have to agree – they are great and it’s not a brand I had ever thought of or had tried before. Needless to say I bought them and have since ordered them in another colour. Made from a heavyweight cotton twill fabric, they are high waisted, but not too high, perfect ankle length and a great fit. I got size 30 and I’m a 12. 

casual trouser based outfits

1. Boden woven frill sleeve t shirt 

2. Free People Leslie leather tote bag 

3. The Great colour block chore jacket 

4. Finisterre Yarrel canvas trousers 

5. Adidas Forum 84 low trainers 


Stripe top from Sezane

Because I don’t think we’ve had a stripe-based outfit for a few weeks and I need to balance out the equilibrium so we all feel in our safe space again. On any given day at home you’ll basically find me wearing a version of this. 

casual trouser based outfits

1. Cos boxy fit stripe top

2. Warehouse chunky flare cat eye sunglasses 

3. H&M embroidered terry towel tote bag 

4. NRBY Betty tapered barrel leg jeans 

5. Nike Blazer mid 77 trainers 

So, next week is either shorts or white dresses and denim jackets. I’m not quite decided yet. Still worried about killing the start of summer if I do shorts…

K x

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