I know, sounds like a kinda random blog post, but it’s definitely one of those things I get asked about by blog readers and styling clients quite a bit.

One gorgeous reader sent me a message the other day asking what the deal is with lengths of Winter pants, and how to wear different shoes (mainly ankle boots) with them – so I told her I’d answer in a blog post! (this one’s for you Kirstyn).

It can be tricky trying to get the length of your pants right, and matching the right shoes to not only keep you warm, but to look great too!

I’ve put together some times (along with pictures – because who doesn’t love pictures!) to give you some guidelines on how to mix and match your pants and shoes this Winter.

Tip #1  – Pick your pants length

We’ve seen quite a resurgence in the 7/8th look for the last few seasons and my tip is that it’s here to stay.

This length generally sits just on the ankle, which is a super-flattering length (yes, even if you are short) as it exposes the slimmest part of the leg – the ankle – therefore drawing attention to that slim part, therefore making the rest of your leg appear as slim.

Even though we’ve seen an appearance from wide leg pants and culottes this Autumn, they are generally in a lighter fabric, so you won’t see too many in the height of winter – maybe this is a leg shape to leave again until Spring.

Tip #2 – What is your heel height?

Also, the other simple rule I often follow is if you are wearing HEELS, you can wear your jeans full length, if you are wearing FLATS, try cuffing your pants/jeans, exposing that lower part of your leg, showing off that slender ankle of yours.


Tip # 3 – Combining the two!

So! Here’s my beginners guide to pants + shoes for the cooler months.


Skinny jeans + flats = cuff your jeans


Skinny jeans + ankle boots = cuff your jeans

Ponte pants/leggings (even though they aren’t pants) + flats = leave them long


Ponte pants/leggings + ankle boots = leave them long.


Basically, if you aren’t sure if you need to tuck or not, then cuff your pants so they sit just on top of your ankle boot. Yes, your legs will still be warm! (invest in some merino socks y’all) and you won’t be constantly tucking your pants back into the tops of your boots all day! Yay!


Again, these are just guidelines! If you want to wear a long top and cuff your jeans then go for it! Hey, I’m sure I do it all the time!

So I hope that helps answer your question a wee bit Kirstyn! But remember everybody, just guidelines – do what feels right for you.

Until Next Time, In Style & Love Always

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