I know, it sounds like kinda a weird topic, but I get asked ALL THE TIME which socks go with which shoes, or boots, and tights are completely confusing too!

So I thought I’d nut it all out for you, and put together some little combos that I find useful when working out how to get your sock-length vs shoe height just right! (it’s al about the big issues here on Chasing Cait).


Let’s start with my favourite shoes in the whole world. Ankle boots. So versatile, and easy to wear with almost anything. BUT the age-old question, what socks do you wear with them? Well ankle socks of course….

Ankle boots+socks

SHOP THE COMBO: Envie ankle boots from Hannahs $179.95 + Simon De Winter chevron liner sock (3pk) from Farmers $19.99

This week combo will work if you want to wear your ankle boots either with a dress and bare legs, or with rolled up jeans or pants. Basically any time where there is a potential exposure of some skin. The socks will sit low enough so as not to be seen, but still give you the warmth (and, lets face it, odor protection) that socks give.

Ankle boots + tightsSHOP THE COMBO: Alias Mae boots $169.95 (on sale) + Max fleece-lined tights $20

If you want to rock your ankle boots deep into winter, particularly with a frock, then tights become your friends. This combo basically is your Winter “skin” to keep you warm, but also it helps elongate your leg.


Hands up if you are loving the Sport Luxe trend right now! Comfy AND fashionable, sign me up! (get some extra Sport Luxe inspo from THIS BLOG I wrote a few weeks back). One of the cool things about this trend is that trainers pretty much go with EVERYTHING! But how do you get the no-socks look, without the no-sock smell….. Invisible socks!

Now not all invisible socks at the same (if they are not good, they slip down off your heel before you’ve even left the house!). So after extensive research from both The Husband and myself, we’ve found what we think are the best on the market…..They are from FOOTLOCKER, yup, the sports shoe store – but sadly they don’t have any online.

These are a good option too (the boys always get better socks!)

trainers and low-cut socksSHOP THE COMBO: Rubi Shoes “jodi” trainers $29.95 + Hallensteins “no show” socks $9.99

If you feel the cold in winter, then you CAN wear a longer sock under you jeans and with your trainers – these socks are more if you want to roll up your jeans or pants and show off some ankle.

Cut-out shoes

If you follow along with my #everydaystyle posts you’ll know I LOVE my cut-out boots and shoes. So what socks do you wear with these? None. It’s commando all the way for any cut-out shoes and boots so I just make sure I give them a good airing out once I’ve worn them all day and before I put them back in their box.

no socks with cutoutsSHOP THE SHOES: Alias Mae “Camille” bootie $249.95 | KO fashion cut out boots from Styletread.co.nz $89.95 | Mr W & Me “factor 35” cut out brogues $139.00

To sock, or not to sock, that is the question. and that, my friends, was the reason for this blog – is WAS a question that a few people have had, so please don’t be scared to ask!

In fact, tell me in the comments below, what little style queries do YOU have that you want sorted on the blog?

Until Next Time, In Love & Style (and socks) Always,


Socks and shoes pinterst image