How to wear trainers with a dress is a style question I get asked a lot! And if you follow along with my #everyday style posts over on Facebook and Instagram, you’ll know this is a favourite look of mine!

It’s feminine, but it’s also practical and comfortable (I’ve got my trusty Kmart (nike-look-a-like) trainers on right now under the desk as I type this!

Thank goodness for the “sport-luxe/activewear” resurgence, it means that trainers + frock is not longer a look reserved for 20-something emo-chicks (no offence 20-something emo chicks!).

But how do you get the look right without looking like you’ve just forgotten you’re heels to change into after the gym? Here’s a couple of tricks to help you get the look right.

Start with a classic trainer.

Ladies – meet Chuck Taylor. He is the quintessential trainer that goes with everything. If “runners” trainers aren’t your thing, then Converse trainers in classic white are the perfect place to start.

chucks with a dress_ChasingCait_How to wear trainers with a dress

Here’s how you can get the look yourself right now!

Classic Chuck taylor Converse trainers_How to wear trainers with a dresss_ChasingCait

SHOP THE LOOK: Witchery off the shoulder dress $139.90 | Glassons straw fedora $24.99 | Converse Chuck Taylor trainers from The Iconic $100.00


Think about your hemline.

Remember that old french woman rule I’m sure I’ve told you before?

If a hem finishes above the knee, a flat shoe is fine, if it finishes below the knee, you need a heel.

This is the basic rule I apply to trainers and dresses (although, as you can see above, I also break that rule occasionally haha!)

shorter_hem_with_trainers_ChasingCaotImages courtesy of Pinterest – find them on my board here

BUT for trainers + dress 101, let’s stick with that rule to start. It’s all about proportion. You want to have as much of your gorgeous legs exposed as you can to make them appear longer and slimmer because you aren’t getting any elevation.

So! Stick to frocks that sit above your knee (and that can be a little, or a lot, depending on how comfortable you are with that)


Slimline trainers work best

If you’re still un-sure about what trainer to go for, look for something a little slim-line. You don’t want to look like you have giant bricks on the end of your feet right? I LOVE my K-mart trainers, I have them in 2 colours, and I actually went down a size to get a more streamline fit (always try a few sizes in everything!)

Kmart trainers in black and white. perfect with a dress

You don’t need a big budget (especially if you aren’t buying them to actually run in!) so this is definitely a look that everyone can get onboard with! Here are a few of my faves (besides the Kmart puppies) that are floating around at the mo.

Trainers with a dress_Chasing Cait

SHOP THE SHOES: (top left) Adidas trainers from $80 | (bottom left) Grey marle “Jodi” trainers from Rubi Shoes $29.95 | (right) Sara sneakers from EziBuy $59.99

So does that give you some tips on how you can rock this look yourself? Let me know if you have any questions about it in the comments below! I’m here to help!

Until Next Time, In Love & Style Always,


one on one iconStill stuck on how to wear your trainers with dresses? Why not book me for a 1-on-1 personal styling session and we can get this look (and heaps of others!) nailed in just a few short hours! Click here for more info!