This season calls for a whole new set of winter dresses – from cosy knitted midis to glam going out dresses for those work parties and Christmas drinks – but I want to focus on the ones that’ll make you feel fabulous.
There’s something extra uplifting about finding that perfect winter dress and let’s face it, we all need something to cheer us up every now and again, especially in winter.
These are the best dresses on the high street right now for under £100 that you’ll wear all season long,
Winter dresses edit
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What do you need to go with your winter dresses?
When temperatures drop, we all have different looks we turn to, whether we’re fans of jeans and trousers with our favourite knits, or our daily go-to is a dress with a winter coat thrown over the top.
If you’re the latter, or you’d like to try out a winter dress occasionally and need some ideas for making an outfit as stress-free as possible, now’s the time to invest in some winter boots to style with your winter dresses – we’ve got your chunky boots, ankle boots and knee-high boots covered.
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It’s also worth looking at where to find the best tights for winter. Wear a sheer pair underneath a midi with knee high boots for extra chicness or try a pair of polka dot tights with a sequin party dress for an extra pop.
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Finally, the only thing left to think about is the best coats for layering over the top of your winter dresses. If in doubt, turn to long coats that fall below your knee for a flattering look – if you’re wearing a midi dress, the fabric will flutter out just below the coat, or if you’re wearing a mini dress, you’ll have enough coat to wrap around you.
Otherwise, look to the other extreme and wear a cropped coat with a hem above your bottom. My favourite styles right now are big fluffy faux fur coats and oversized aviator jackets with cosy faux shearling linings. Shop them all in our winter coats guide.
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But now onto the main event – this season it’s all about the best winter dresses:
1. Short knit dress
This H&M dress comes in khaki, dark beige and cream – and I love them all! Wear them with stompy boots and sheer tights with a teddy bear coat wrapped around you.
2. Midi knit dress
If you’re looking for a knitted dress that’s more figure-hugging, then this French Connection dress has a flattering ribbed texture, pulling you in at the waist and flaring out at the hem.
3. Knitted Skims dupe
There’s a reason those Skims dresses (and dupes!) are so good, and this COS knitted tube dress ticks all those minimalist, flattering, and versatile boxes.
4. Silky midi dress
A do-it-all dress, this Never Fully Dressed midi (in sizes 6 to 24) can be worn day to night, just pair with long boots, a longline coat and lots of jewellery.
5. Floral midi dress
There’s not-so-groundbreaking floral dresses, and then occasionally there’s some that stand out from the crowd. This M&S dress is one of those, with its black lace detailing at the yoke and hem, long sleeves and tiered midaxi fit that makes it great for winter. The soft viscose fabric that drapes in a more expensive looking way than your average (especially when belted in at your waist!)
6. Floral puff sleeve dress
For an easy look, you just can’t go wrong with throwing on a dress with some chunky biker or Chelsea boots. The floaty smock silhouette of this Nobody’s Child dress is perfect in a lime green print that’s pretty, but punchy.
7. Sequin mini
Bright barbiecore pink + sequins + mini = your ultimate party dress for only £35.99.
8. Sequin midi
If you’re looking for festive sparkle, but on a dress in a flattering midi length, this M&S one is a winner and is reminiscent of those coveted Vampire’s Wife dresses.
9. LBD
If head-to-toe sequins aren’t your thing, add just a touch of sparkle to a classic LBD.
10. Colour pop mini
One for your inner 80s disco diva, this purple mini dress with exaggerated puff sleeves and a high neck would look amazing with a pair of polka dot tights and knee-high boots for a winter night out.
11. Black maxi dress
If you’ve got a smart black-tie occasion in winter, you can’t go wrong with a classic black maxi dress. For a new season update, look at fringing and extra detailing like this dress from Ghospell.
12. Cocktail dress
Shopping for a cocktail dress code? Read all the dos and don’ts in our cocktail dressing guide. This River Island bow midi dress has caught my eye.
13. Reformation dupe
We love a Reformation dress dupe here at Eliza and this Oasis dress is a serious contender.
14. Alessandra Rich dupe
Here’s a high-street alternative to Kate Middleton’s iconic Alessandra Rich polka dot dress, a perfect winter option in burgundy.
15. Velvet mini dress
We can’t get enough of velvet dresses for winter and top of my wish list this year is this one from Sister Jane.
16. Velvet slip dress
We keep an eye on Zara’s new it-dresses, and my prediction is that this is a new contender for the list. This midnight blue velvet slip dress won’t be around for long.
17. Cut out silky dress
This high-neck dark brown satin dress from Nobody’s Child gives the cut-out trend a sophisticated spin for winter.
18. One shoulder slip dress
Asos has elevated the noughties slinky slip dress for a black tie occasion with this asymmetric draped style.
19. Organza midi dress
The dreamy combination of velvet shoulder ties and floral organza make this dress look extra special – no one will believe it’s under £99!
20. Organza mini dress
For a statement-giving and mini organza dress, Asos have delivered. Wear with over the knee boots and sheer tights by day or party heels and statement jewellery by night.
21. That red dress
A winter edit just wouldn’t be the same without a little red dress.
22. Leather pinafore dress
The cutest leather dress around, layer this pinafore with your favourite statement blouses for work and drinks out after.
23. Denim dress
If you love a midi, this is one of those comfy but smart styles you know you’ll turn to all the time when it’s rainy, cold and you have no idea what to wear.
24. Shirt dress
I’m loving this gathered shirt dress from COS for a classic winter work wardrobe investment. It’s suitably minimalist so you could get away with wearing it every week, but with the expensive-looking ruching and tailored fit, it’s not a dress you’d get bored of quickly either. Shirt dresses are big news this season, too.
25. Cord dress
For the ultimate cosy feel in winter, I love anything made from corduroy.
26. Tweed dress
This tweed dress from Reserved will look chic and keep you cosy from wearing on workdays to dressy weekend events, especially if you layer it with a fine knit roll neck jumper underneath.
27. Under £30 party dress
This dress is universally flattering and looks incredible on. Dress it up with XXL statement earrings and metallic platform heels.
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