Best dresses to wear in winter 2021

By Ellie Davis

When the summer rears its long-awaited head and the temperature starts to increase, we instinctively swap out our jumpers and jeans for lighter floral dresses. It’s not ground-breaking, it’s just what it is.

But as the cold approaches, we can’t help but want to maintain the ease of the dress for the winter weather. Throwing on a frock simplifies the entire getting ready process and minimises last-minute morning indecision.

At the crux of it, you only really need to think about one item when you throw on your clothes in the morning. The rest just falls into place. Pair with tights, a jumper, a coat and boots and you’re ready to brave whatever the British winter has in-store. So practicality wise, it’s a win but what’s more, on the comfort level, they are unrivalled.

If you’re anything like us, layering up our wardrobe is the thing we covet most about the colder time of year. Summer fashion is a minefield so the ability to bundle up in knitwear and the season’s crop of covetable coats softens the blow of the changing of the season. Mourning the summer stops at the sartorial offering.

Warm winter dresses are very much a thing. Replacing traditional thin sheaths with long-sleeves, wool and cotton fabrics and minis with ankle or knee grazing hemlines, you can curate a hardworking arsenal of statement and subtle frocks that are demure yet chic.

With the return to office life, you’ll need these pieces in your rotation. Working from home certainly had its perks sartorially with loungewear and casual clothes as standard but there’s something about dressing up that gives a level of self-confidence that no doubt impacts productivity.

See our pick of the best dresses for the winter below.

Robin Cashmere Sweater Dress

This dress from Reformation will have you longing for the colder weather. It has a cashmere construction that is sumptuously soft with a slim fit and turtleneck design. There’s also a sexy side slit for a subtle flash of skin. It comes in black and an oatmeal hue.

Buy now £300.00, Reformation

Buttoned Polo Midi Dress

Apple green is everywhere at the moment and this midi dress from & Other Stories is an easy way to incorporate the shade in your winter wares. The midi sits just below the knee with a polo collar and a self-tie detail to enhance the silhouette.

Buy now £75.00, & Other Stories

Floral Print Dress

You needn’t reserve your florals solely for the warmer weather. With this frock, the playful print enters the realm of winter dressing with a red and white colourway set to give your traditionally monochrome wardrobe a pop of colour.

Buy now £29.99, Zara

Mel Swirl Floral

In an elegant velvet fabric, this dress is ready and waiting for the weather to turn so you can wrap up in the luxe silk blend. It has a fluted sleeve, V-neck and front leg split that give it a sensual look, while remaining covered up enough to add to your work rotation, especially when layered over a turtleneck as pictured. The swirling floral print has a 60s feel.

Buy now £325.00, Rixo

Staud Castle cutout knitted midi dress

This knitted dress from LA label Staud has a playful heart cutout at the chest to give it a fun and feminine look and make it both a work and weekend-worthy style. Sitting at a midi length, the piece also features a slim fit and high-neck design.

Buy now £245.00, MatchesFashion

Gathered Midi Dress White

In Cos’ signature aesthetic, this is a refined piece enhanced by well-placed gathered detailing that adds structure and offers a figure-flattering look while remaining easy and effortless. The dress is crafted from a soft modal and cotton with the added enhancement of puff sleeves.

Buy now £89.00, Cos

Tie Dye Rib Roll Neck Dress

With a throw-on-and-go quality, this roll neck dress features the 90s favourite tie dye print that has been given a new lease of life in recent seasons. The pared-back palette of green and black puts a more wearable twist on the traditional garish pattern.

Buy now £31.20, Warehouse

Lottie Longline Knit Dress

Fill your back to the office wardrobe with workhorse styles like this knit dress from Aussie favourite label Forever New. With very little effort required, it oozes with sophistication thanks to the figure-enhancing slim fit silhouette, tie belt and slip-on design.

Buy now £80.00, Forever New

Julius Dress

Your winter wardrobe need not only consist of neutral hues, Reformation’s Julius dress is offered in this pattern entitled Venture. The emerald green shade is muted enough for the colourphobes, but still offers a statement with the design. The silhouette is fitted at the bodice with a relaxed skirt and a belt to tie it all together. It also comes in a forest green, snow leopard and cottage floral print.

Buy now £300.00, Reformation

Mango Knitted Midi Dress, Light Beige

The Spanish high street hero nails the effortless elegance aesthetic with this hugely versatile dress in a light beige hue. The colour makes your job that much easier as it can be styled with pretty much any accessories or coat. The chic knit style is enhanced by button detailing and a scoop neckline.

Buy now £49.99, John Lewis

Voluminous Tiered Maxi Dress

While this frock from & Other Stories has a voluminous, loose fit, the Scandi minimalist design still looks sophisticated and put together. This is the kind of piece that acts as a sartorial stepping stone from your cosy loungewear. You only need to throw it on and you’ll be ready and raring to go in a few seconds flat.

Buy now £95.00, & Other Stories

Whistles Wool Blend Collar Knitted Midi Dress, Oatmeal

This dress from Whistles may resemble an oversized jumper and yet it sheds all the informal connotations of the casual wear staple. At just below knee-grazing length, it has a smartened up aesthetic with its collared neckline. Comfort is also key with the wool blend construction.

Buy now £139.00, John Lewis

Ganni Puff-sleeve ripstop wrap midi dress

One of fashion’s favourite labels, Ganni is injecting a bright green hue into your cold weather wardrobe with this frothy frock. It has puff-sleeves with a V-neck design as well as button embellishments. The fabric is a lightweight ripstop that is made up of small checks.

Buy now £225.00, MatchesFashion

REMAIN Birger Christensen Joy ribbed-knit midi dress

You can count on the Scandi labels for their ability to up the style stakes even when temperatures drop - and REMAIN Birger Christensen is leading the pack with this sophisticated ensemble. It has a ribbed knit construction with an all-over white hue given an interesting detail with tonal blue at the collar and trims.

Buy now £190.00, Net-A-Porter

Poplin Panelled Midi Dress

Modern iterations of the pouffy tiered dress have taken on many forms in the last few years but Zara proves its still front and centre of the trend with this black midi. Smocked detail, puff sleeves and most importantly of all, pockets make for a dress you’ll wear time and time again throughout the winter.

Buy now £29.99, Zara

Belted Shirt Dress Beige

Utilitarian aesthetics are a surefire win when it comes to boardroom dressing and this version from Cos has style in spades. This is another dress with pockets and if that alone doesn’t win you over, we don’t know what will.

Buy now £79.00, Cos

Floral High Neck Midi Tea Dress

Don’t sleep on M&S’ ever-growing selection of dresses this season as the brand has a stellar selection that includes this tea dress in a few different patterns. The flattering style sits at a knee-length with a high collar and empire-line bodice. Alongside the red, blue and yellow floral print pictured, there’s also a black and white and pink. We’ll take all three.

Buy now £39.50, M&S

Dolly Romantic Rose

Wedding guest dressing made easy, this piece from Rixo with the Romantic Rose floral print can also be dressed down by throwing on a jumper. With a sweetheart neckline, the bodice is crafted from a luxe velvet that cuts at the empire line to reveal a stunning rose pattern.

Buy now £295.00, Rixo

Roll Neck Maxi Dress Blue

The graphic print of the piece speaks for itself, and when combined with this construction, makes the ideal winter dress. It has a very welcomed stretch that adapts to the contours of your body that flows into a pleated A-line skirt. The long-sleeves are made all the better with thumbholes to keep your fingers warm throughout the winter. The Tencel fabric is also sustainably sourced, made from the eucalyptus tree where all the chemical and water are recycled.

Buy now £69.00, Cos

Tamara Sheer Maxi Dress

If you’re not familiar with hush, the brand specialises in wearable everyday essentials with premium constructions - and no premium price tags. With an all-over ditsy print, this piece is sure to be an MVP in your dress arsenal offered in a semi-sheer chiffon that is helpfully lined.

Buy now £119.00, hush

Printed Gathered Sleeve Open Back Midi Dress

Warehouse is another label that is nailing its dress offering this season. The brand may have been recently acquired by the boohoo label but it’s maintained its signature refined aesthetic with pieces that look and feel far more expensive than they are. This maxi dress has a pretty floral detail with bold tones of pink, red, white and lime green - a colour spotted everywhere at the moment. It has an open back design with a tie fastening.

Buy now £29.50, Warehouse

Low turtleneck ribbed dress

When the inevitable sartorial indecision arises, you’ll be glad to have a dress like this midi from Monki. It’s just easy. The playful colour combination and ombré effect makes it appear like you’ve taken far more thought and care to put it on than the reality as you don’t need much else to create a chic look. It’s also a win in the practicality department, the piece had long sleeves complete with thumbholes.

Buy now £30.00, Monki


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