How to wear Trainers & Sneakers with Dresses & Skirts

How to wear Trainers & Sneakers with Dresses & Skirts

In the past, the only time I wore trainers was to go to the gym or to run across London (metaphorically not literally) to make the mad dash to work – where I’d then change into heels.  I did own sneakers that weren’t meant for exercising – brands such as Converse, Adidas and Puma were some of my ‘fashion’ go to sneakers however I always wore these with jeans.  I’m a ‘girls girl’ and a lover of pretty shoes and trainers/sneakers just felt a little too ‘boyish’.

Three things happened. A move out of London meant a lifestyle change (more country walks and park life than city living). I became a mum and as a mum I always seem to be in a rush – school drops offs, pick ups, piano, drama, swimming the list goes on and lets not even get into the amount of times I have to pop to the supermarket because we’ve run out of stuff. Finally largely thanks to former Celine creative designer Phoebe Philo trainers became ‘wearable’ outside of the gym and by all ages.  Phoebo would often be seen in a classic white sneakers at her shows, this did much for the likes of Adidas Stan Smiths, New Balance, Nike and many more.

Phoebe Philo 2011 A/W Celine show (Paris)


Over the last few years trainers and sneakers (there is a difference, one can be worn to the gym the other is just a fashion item) have become more and more everyday wear for me.  I feel they give my summer wardrobe an edge.  So many friends have asked me how to go about styling said footwear with more feminine wardrobe items. Whether your go to outfit is a swishy skirt, midi-dress, tea dress or playsuit, believe me you will be able to find a pair of trainers or sneakers that work with it and for you. 

The great news is that the street style look based on comfy casuals and chic fashion is just perfect for ‘trainers’.  Trainers look just as fabulous with your Spring/Summer wardrobe as they do with your Autumn/Winter clothes.  The even better news is that there are some seriously fabulous options out there to suit even the fussiest of customers. 

Not long ago I’d have said that certain styles of trainers were too boyish to pair with feminine dresses and swishy skirts,  however the oversized Balenciaga Triple S has changed the playing field and introduced a trainer that is neither dainty nor feminine but just seems to work. 

So whilst I love the oversized trainer, I do feel a little ‘mutton dressed as lamb’ in them. So it is about finding a style that you love and feel happy pairing with your dresses and skirts. There are so many trainer and sneakers out there so my advice, stick to a style that you feel comfortable in and that flatters your ankles and feet (I’ve just bought a pair of Nike Air Max, my girlfriend feels that whilst my size 4 feet look great in them her feet would not suit that style).

For those of you who are new to trainers with dresses and skirts, the easiest way is probably a simple sneaker / canvas style trainer. The workout trainers and oversized trainers are a little harder to wear and will depend on your individual style and preference. I personally love the look but appreciate it’s not for everyone.  

So with that in mind I’ll start with the SUPERGA and CONVERSE, easy to wear, fuss free and look great with all spring / summer wear.  Incredibly affordable and colour ways to suit most tastes.  The white slightly stresses me out but hasn’t deterred me from buying a pair (or two) of Converse in the past.  These brands are traditionally known for their canvas sneakers but have a great range of leather ones too (easier to keep clean!).  Alexa Chung is a fan of both brands and has collaborated on a range with Superga. 


 VANS , another affordable brand who’s range and designs are simple.  A classic style that is easy to love.  These look equally stylish with jeans as they do with dresses and skirts. 


Created by Claire Burrows former head of ALDO uk the AIR & GRACE brand are a firm fashion favourite. Sneakers that not only look fabulous but as a result of their unique patented Tender Loving Air® comfort technology, created from three different layers of memory and recovery foam cushioning are also incredibly comfortable.  

VEJA is no ordinary brand Sébastien Kopp and François-Ghislain Morillion founded the Parisian brand in 2005.  This brand places as much importance on the environment and ethically sound practices as it does on style and design.  These sneakers are made in Brazil, the only country to have organic, fair trade cotton and wild rubber.  The sleek, subtle branding and cult following help to make VEJA a brand to watch. 

The Swedish trainer brand AXEL ARIGATO is relatively new to the market.  They launched in 2014 and have been creating sleek, minimal and exceptionally well-crafted trainers since launch. Axel Arigato takes inspiration from its country of origin, as well as Japanese design, to create contemporary trainers with a difference. Handcrafted in Portugal, think fine Italian leathers, calfskin linings and Margom rubber soles (I think I need a pair!).

Another relatively new brand to the market that I’m loving is CRIME LONDON.  Launched in 2012 by the Kistermann sisters, Lisa and Jessica.  The designs are inspired by the vibes of London’s underground districts. Crime London is all about being dynamic while attaining a cool lifestyle.


GRENSON, a British brand that has been around since 1866. Originally founded by William Green today the brand is owned by Tim Little who has taken the business and brand from strength to strength.  Heritage, good quality and classic are words that all spring to mind when I think of this brand. Some great classic simple styles that would work with dresses and skirts alike.

RUSSELL & BROMLEY, were first founded in 1873 and still continues to be a family owned business.  I grew up with this iconic brand and I have to say when I think of Russell & Bromley I don’t necessarily think of sneakers. A girlfriend asked if I had seen their recent range and I had to admit I hadn’t.  

I was not sure what to expect and was surprised to see how modern and fresh the range looked, definitely a contender in my books. 



The GOLDEN GOOSE Deluxe Brand was launched in 2000 by Francesca Rinaldo and Alessandro Gallo, two young Venetian designers.  The Golden Goose sneaker has a modern style with a vintage feel. I have to admit that I’m not totally sold on the look of these trainers, I like my trainers to look ‘new’ and these look ‘well worn’ – I’m guessing that is the vintage element. I have many friends who love these and look great in them.  

The ADIDAS STAN SMITHS, a classic sneaker worn by many. They are available in a variety of tongue and cuff designs so you can pick a colour-way you feel work with your wardrobe. Some may argue that these are no longer ‘cool’ I say that they are still incredibly popular and will still continue to be worn by many. 

NEW BALANCE is one of my current favourites.  I have recently just bought a pair of the iconic New Balance grey 574 and I love them.  Not only do they go well with dresses, skirts and jeans but are also incredibly comfortable.

Like all the other sports brands REEBOK and PUMA also have classic styles within their range that may appeal on both price and simplicity of style.  Clean looking sneakers that I feel would work across your wardrobe.


Moving on to the biggest trainer brand in the world NIKE.  Nike first launched in 1964 and was known as Blue Ribbon Sport. It officially became Nike, Inc. on May 30, 1971. The name Nike means the Greek goddess of victory.  I love the Nike Air Max 97 and have just bought a pair but the Nike Fly Knit also looks set to become a huge hit.


Finally the designer sneaker; BALENCIAGA, GUCCISAINT LAURENT.  If budget is not an issue there are a multitude of designer sneakers to choose from. From the oversized Balenciaga Triple S to the more classic Saint Laurent these are just some of the sneakers out there.  I say sneakers as no matter how oversized they are these trainers are not meant to be worn in the gym. These beauties are all about style and status symbol.  At some of these prices you would have to LOVE them a lot and want to have them in your collection for more than one season.  At this point it also becomes easy to see the similarities between brands and where styles and designs start to overlap. 

If you have made it this far well done. I may have given you more than you can handle. I’m sorry. I really do need to learn how to not be quite so ‘thorough’. These are some of the brands I either own, or would like to buy. I haven’t even looked at high street sneakers and trust me there are some great versions out there costing considerably less than some of these.

Whatever your thoughts I hope that I have convinced you to pair your sneakers or trainers on with your skirts and dresses. Give it a go and if you do send me a pic via instagram.

Love Chet x


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