Many of us are asking the question, how to wear winter dresses? As the days are getting shorter, and the warmth of the summer really seems a thing of the past.

Does all this cold weather mean giving up our dresses?

We all know that being cold in winter is really rubbish, it seems to somehow hit your bones and keep you slightly shivery all day. 

This fear of being cold often leads many of us to stick with the same types of outfits in the winter months. The old reliable woollen jumper and thick dark colour trousers. 

woman standing on street holding her hat in the air smiling. Black winter coat, black winter dresses, black hat.

The thought of wearing winter dresses usually brings with it two concerns. Either you spend your whole morning searching for your old, slightly tattered thermals. Or you spend the whole day trying to warm up after leaving the house in the morning. 

But, we think that just because the weather has turned it doesn’t mean that your dressing should too. Our advice will show you how you can feel both comfortable and stylish and confident in the cooler months. 

We have found you some great advice to make sure you are feeling both warm and stylish this winter season. 

Roll necks can make any dress a winter staple

blonde woman standing against a wall wearing a grey turtle neck jumper

Turtle necks are a classic chic look on their own, but when wearing a long-sleeved roll neck under a shift dress, it can be ‘cold-weather-appropriate perfection.’ 

Or for some extra warmth try a turtle neck under winter dresses with long sleeves.

Stylish ways of wearing winter dresses with black tights

woman standing under arches in a pink coat and black boots and tights.

Okay, so we do know that this isn’t a particularly revolutionary trick here. You have probably been wearing tights since your mum would dress you in your very first school uniform. 

But, there are a few ways of styling winter dresses and tights to take this from a more basic to fashion-forward look. 

Emma Spedding from Who What Wear describes how we can achieve this look. ‘The easiest way to look great in tights is to go with all black, for a classic look. But if you want to stray from black, make sure the colours are still winter colours (aka no brights or neons) and that there’s some black in the top half to match the tights’

If you are still worried about the warmth aspect, try fleece-lined tights. Although they are a little more expensive they will really lock in a layer of heat for you so you will want to wear your winter dresses every day. 

Wearing winter dresses with boots 

woman wears a pink coat, skirt and bag and grey jumper and over-knee boots. Stands against white wall.

We know there are some people who simply can’t stand tights. Everything from the feel of them on your skin to their ability to keep falling down throughout the day. Whatever reason you have, we know that for some people, tights just aren’t for them.

If this is you, fear not, we are here to help, making sure you can wear your winter dresses. 

A very stylish way of wearing winter dresses without tights this season is by pairing your dress with over the knee boots. 

woman wearing a black swing dress, with another image of black over the knee boots. Woman wearing silver earrings. Images arranged on a pink background.
To get this gorgeous night outlook yourself check out the Stella Bardot Drape Dress, Over the Knee Boots and Earrings. Click here for some more beautiful dresses.

Styling a pair of over the knee boots with a midi-length skirt means you are able to go tight free. As the skirt length of this style of winter dresses cover the tops of the boots ensuring no skin is on show. 

If you are a fan of tights this can also be a great look to wear with a shorter skirt. As Santi says ‘wear a dress that hits just above the top of the boot, and top with a jacket or coat that’s a similar length (and colour!) of the dress for extra sleekness.’

Wearing winter dresses maxi 

woman wearing grey headscarf, blue coat, maxi dress, pink belted bag and white boots. Poses in front of a Cathedral. Pigeons fly to one of her hands.

We know that maxi dresses are often associated with the warmer months, making us think of breezy beachside living. But, this doesn’t mean that you should be afraid of wearing some winter dresses maxi. 

Wearing a Maxi dress with a matching colour leather jacket or cropped peacoat looks great. As Josie Santi says ‘channel your inner mary Kate and Ashley with a look that’s just as boho-chic as it is warm.’

Just try and avoid coats that are too long as they might make you look more on the bulky side. If you are worried about being cold, why not add a turtle neck under your dress?