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What to wear with your hi-top trainers

First up, I’m not sure if it’s hi-tops or high-tops, but you know what I’m talking about, so today we are running with hi-tops for the sole reason it’s two letters less for me to type. You may also think at this point, ‘Hold on, I’m too old for this kind of shoe caper’, but I say, ‘No, no you are not’. I also say that hi-top trainers are the sportswear equivalent of a nice pair of winter boots. If only because they will keep your ankles slightly warmer than regular trainers. Ok, I’m clutching at straws here; I’m basically writing this post for my own benefit as I just really like wearing hi-tops and I shall never grow out of loving them.

I can chart my love of a hi-top back to the school French exchange trip when I was 13. It was in a shop in Paris that I bought my first pair of Converse. I got a green pair and my friend Tansy got black. We also wore jeans with braces and smoked our first cigarettes on that trip. You would have thought a filterless Camel would be enough to put any 13-year-old off smoking for life, but no, it was the 80s, and we persevered with our smoking practice until it became a habit. On our return to the UK we moved on to 10 ‘Benny Hedgehogs’ or “Silky Sluts’ if we could persuade the local newsagents to sell them to us. If not, we settled for ‘Honeyrose’ herbals, which for some inexplicable reason you could buy at any age from Holland & Barrett, the health food shop. How times have changed.

I digress. This isn’t a blog about my teenage exploits, it’s about what to wear with your trainers, but they remind me of those times and I don’t feel like I’ve ever really grown up that much. Happy to say that I did give up the fags once I got pregnant 18 years ago though*…


A pair of loose-fit boyfriend jeans and hi-tops are always a go-to casual look for me. Do you have outfits that you put on and that are just ‘you’? That you return to time and time again? I feel most like myself when I wear something like this. Nike Air Jordans are one of my current favourite trainer styles – they are supremely comfortable but they can be scarce. The Nike Dunk is a good alternative and a very similar style.

1. Bella Freud oversized 1970 merino wool jumper 

2. Abercrombie quilted liner jacket 

3. Agolde Wyman straight leg organic cotton jeans 

4. Rock and Ruby matilda cotton socks 

5. ALS gold leather Shaw sling bag 

6. Nike Dunk high 70 trainers 


This is one that could take you from day to night. A great jumpsuit, trainers, blazer and cool clutch bag, this is another of my go-to looks when I can’t be bothered to think about what to wear on a not-too-dressy night out. We’ve already established that this type of night out is my favourite. I tend to walk a lot even when I go out of an evening, so heels are rarely an option. Comfort will always come first, but it doesn’t have to be at the expense of style. Look for metallic or embellished hi-tops as an alternative to a heel.

1. By Iris Colby utility jumpsuit 

2. Zadig and Voltaire Rock Wings clutch 

3. Loel & Co silver spiral twist bracelet 

4. Weekday Luciana wool oversized blazer 

5. DATE Sport high top trainers 


This look really should have been on last week’s blog, but it works for today too. Usually I find the classic Veja trainers a bit overrated and not very comfortable, but their hi-tops are actually really good and need no breaking in at all. Trainers, in my opinion, should never need breaking in; they are essentially sportswear, so they really should be comfortable from the get-go. Also, this Matalan jacket is reversible – I have it in green from a few years ago (two-for-one and at a great price).

1. Arket cable knit responsible wool jumper 

2. Matalan Mink reversible jacket 

3. Genevieve Sweeney Samar merino wool stripe socks 

4. Toast barrel leg organic cord trousers 

5. Veja Roraima suede trainers 


Converse. Still the most classic hi-top there is. I recently replaced my VERY old pair with these off-white vintage ones I featured in the French girl post, and they literally go with everything. I forgot how useful they are. I’ve kept this look monochrome because I feel that’s what stylish French ladies would do.

1. M&S Mens extra fine merino wool roll neck jumper

2. Loewe small black leather puzzle bag 

3. Tu mono herringbone jacket 

4. Levi’s ribcage straight ankle jeans 

5. Converse black and white Chuck 70 high trainers 


This is really another version of outfit number 1 and something I wear all the time. The Nike Blazers are also a VERY comfortable pair of trainers; I wear mine when I do my (now twice-weekly, what have I become?) strength training because they give great ankle support when you’re attempting your best Geoff Capes impression at the gym. The only downside – and this goes for all hi-tops, really – is that, in the words of my 15-year-old, ‘They take a million years to get on and off’. Slight exaggeration.

1. Thought recycled polyester puffer jacket 

2. By Pollyanna vintage white boyfriend fit T shirt 

3. Levis 501 straight crop jeans 

4. Mango button knit cardigan 

5. Nike Blazer Mid 77 trainers 


This is to give you an option for a party look that you can wear with trainers. They go best, I think, with longer, wide-leg trousers. Pair with a bit of sparkle up top and a simple fitted top, or even a body if you feel brave enough to attempt an evening negotiating the popper situation.

1. Monsoon animal sequin velvet jacket 

2. Louise Wade Bowie flash sterling silver earrings 

3. Cos long sleeve bodysuit 

4. Per Una velvet side stripe wide leg trousers 

5. La Redoute Soho leather trainers 

I had a request to do a round-up of my favourite designer and high-end handbags, so I might do that next week. I will also try to add purse-friendly options too. 

K x

*unless I’m really drunk and someone has a menthol on offer.

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