Styling Dresses For Winter

Styling Dresses For Winter

You definitely don’t have to wait until summer to wear dresses during the day in my book. As a lover of all things feminine, I love wearing dresses; and as a lover of swirling and spinning & prancing around, I am definitely not one for giving up on my love affair during the colder months.


I love how effortless dresses are, it’s whole outfit in one. You look like you’ve put a whole lot of effort in when really you’ve not even given it a second thought. It’s happened to me so many times, people will say to me “oh I wish I had time to dress like that” or “I wish I could be bothered”. My reply? Something along the lines of… are you joking? I literally threw this over my head in 2 seconds without even thinking and didn’t even have to waste time putting an outfit together or hunting for “those jeans that go best with that top”.


To me, dresses are effortless, a key component of classic style and a vital part of my wardrobe. Not everyone as big a fan as I am which is understandable, but if I had to pick something to epitomise my style as a whole, it would most likely be a dress.







So, I thought I’d share my top tips for styling dresses during the colder months for those of you who share in my passion and the belief that one can simply never be overdressed.



I believe in overdressing. You never know where the day will take you.


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                                 *Boots & Bag ~ Both Zara




Photography by @bella_ivanovaa


Midi Dresses & Ankle Boots

Midi dresses are a personal favourite of mine all year round for daily wear. I love how midi dresses give such a classic and sophisticated look, allowing you to look well put together but are still super stylish. A floaty skirt with a pinched in waist on a midi dress creates a great silhouette.

In winter, I swap my summer heeled sandals for heeled boots worn with midi dresses. Recently I’ve been obsessing over sock boots, but I especially love how they look with a dress. By clinging to your leg they create a sleek look, keep in line with the femininity of the dress, adding a little sass but without looking clumpy or overbearing.

OTK Boots

Love a mini dress? Over the knee boots are your answer! Keeping your legs tucked away from the bitter winds with just the right amount of thigh on show = the perfect outfit. And again, this is the most effortless combination. I’m still in love with pairing my grey All Saints dress with my OTK boots, it’s a style thats carried me right through from Autumn and will continue to Spring (and probably summer in Glasgow, lets be real).

OTK boots allow you to continue wearing your cutest dresses all year round without freezing your little legs off, and the best part? Your legs don’t even have to be perfectly shaven since their tucked away inside your boots? emmm WIN.

I invested in my over the knee boots (linked below) due to my genuine NEED to wear dresses all year round, I love how they look with literally every single outfit I throw on and investing in quality really does pay off. But if you’re not ready to invest – there are so many great options out there for all budgets! I’ve even linked some below, you can click on the image to go directly to the shopping site. You’re welcome!

Jumper Dresses

A cosy jumper…but as a dress? A fashion peak in my opinion, does it really get much better than this?? A jumper dress is a way to look snuggly and stay warm while also still channelling your love of dress wearing! My favourite way to style is a jumper dress with my OTK boots and a big coat.

They’re are so many types of jumper dress, from super chunky to much lighter fabrics. I’ve definitely bought my fair share and I’m always on the the hunt for a good ol’ jumper dress, so please lemme know if you have seen any good ones lately! In the meantime, I’ve linked some below for you to have a browse.

Tights vs. No Tights

Finally, the big debate. I sit kind of in the middle on this controversial topic. On one hand, I do absolutely think tights are the secret thief of all style, if worn badly that is. I do however, still love a little pinafore, roll neck and chunky black tights. I think it looks super cute.

It can be a tricky thing to master if tights have become best friend, they can definitely make or break an outfit. The trick is to think of them as a last resort. You definitely don’t NEED them just because it’s Winter. It’s not illegal (well here anyway) to have a little bit of thigh or ankle on show in the winter months, use the tips I’ve mentioned to keep a sophisticated look.

But if your outfit it looking super cute with some chunky black tights, or super sassy with a sheer pair and a leather skirt ~ then go for it! It’s your style, do what you think looks best on you!


I hope you’ve enjoyed this light-hearted fun fashion post, leave me a comment with any other fashion blog post ideas you’d like to see!


Lots of Love,

A|W x

This post is not sponsored. I use affiliate links via shopstylecollective to provide you with the best shopping experience as a reader. This simply means that if you purchase via one of my links, I receive a very small amount of commission as a way of thanks. This however, does not impact the price you pay for shopping in any way, the price is always the same regardless. I always appreciate your support.

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