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12 of the Best Maxi Dresses in Winter Season and How to Wear Them!

Maxi Dresses in Winter Season

Maxi dresses, rather like skinny jeans, show no sign of going out of style and with very good reason.  One of the most versatile items that you can have in your wardrobe, many maxi dresses in winter season can be easily taken from day to night and will see you through your work day and straight into your dinner date – all you need is some additional accessories and a bit of make-up to completely transform your look. Maxi dresses in winter season are sure to be one of the big fashion stories.


Although most people think of them as a summer staple, maxi dresses in winter season are completely on-trend, and even when they are on the lighter side they can soon be warmed up with thick knitted cardigans and on-trend jackets to ensure that you stay stylish and warm. This year, Vogue is betting on lots of interesting trends that will help you take a plain maxi and bring it bang up to date – sportswear is one of the big winners from the big four fashion shows this year, so think about teaming your dress with Chucks or trainers for a casual look. Another big win is anything military – maxi dresses in winter season would look great with the army style great coats that were seen at Prada, Miu Miu and Burberry, and they also work really well teamed with boots. One of the many benefits of maxi dresses is that they are mostly reasonably plain, so you can make a huge statement with your jewelry and accessories – Balenciaga and Stella McCartney were both showing ultra-chunky earrings using everything from huge safety pins to acrylics.


We’ve created the definitive guide to the best buys on the market right now, and we’ve also included some helpful tips to aid you in getting the most from your winter wardrobe.  Without further ado, here is the best of the best for this season – we’ve got something for every shape, style and budget.


Best Budget Maxi Dress


1.      J.D.Y High Neck Ribbed Maxi Dress


This rust colored maxi dress from Asos is one of the best bargain buys of the season – in ribbed cotton with a high neck and side split, it can be dressed up for work or down for the weekend.  Some chunky boots and a biker jacket will create an edgy look perfect for winter gigs or shopping trips (and will keep you right on trend – see shows from Prada and Burberry for military style detailing), or it can be layered with a long-line waterfall cardigan and a thick belt for those chilly winter work mornings. J.D.Y specializes in jersey and denim, and their knits (like these maxi dresses in winter season) are well known for their softness and comfort – this is the perfect dress to take you from morning through to evening by changing just a few key accessories. Team this simple stunner with neutral make up and smooth sleek hair, as the color itself is bold and doesn’t need extra embellishment. Best of all, at just £18.00, it won’t break the bank. You could also work in some of the velvet that was everywhere on this season’s catwalks with a simple or beaded velvet scarf – think jewel colors and crushed texture to go with this one.

Best Luxury Maxi Dress


2.      Phase Eight Black Betsy Sequinned Dress (£350.00) – Next.com


This stunning black, embellished maxi dress is definitely on the pricey side, but will also definitely make a statement, whatever occasion you choose to wear it on. Sequins were also huge on the catwalks at this year’s London, Paris and New York fashion weeks, so this is another opportunity to buy something on trend, yet undeniably classic. From Next’s signature ‘Phase Eight’ collection, it is softly tailored with chiffon over dress and sequin detail from the neck line to the hem. Only minimal accessories are needed with these types of maxi dresses in winter season, as the heavy detailing speaks for its self – some simple, strappy heels in a matching or contrasting shade are all that are required to complete the look. Although there are cheaper dresses on the market, this one topped the list because of its mega-flattering cut and hand finishing – it’s also classically cut and designed so it doesn’t have to languish at the back of the wardrobe having been worn only once! This exquisite dress begs for lashings of smoky eye make-up and dramatic lashes – keep the lips nude to avoid detracting from the dress itself. It is well worth looking at the way McQueen styled their models at this year’s catwalk shows to get a good idea how best to work this look – dramatic but understated is the name of the game when it comes to heavy embellishment.

Best Work Maxi Dress


3.      Cameo Rose Blue Stripe Maxi Shirt Dress


One of the best things about this classic blue pinstripe maxi dress is that it is currently on sale for an amazing £10!  This really is the perfect work dress, and as it is a polyester mix, it won’t crease if you have to spend long periods of time sitting or travelling. It comes with a simple, matching fabric sash belt but there’s no reason why you couldn’t change up the look by teaming it with a thick leather belt to match your shoes and bag. The side splits are modest, and I’ve even seen a similar dress to this teamed with thick black tights and chunky boots, which looked surprisingly good. It definitely works best with simple heels and a blazer style jacket though – don’t mess with a classic. Team this one with a slick of liquid eyeliner and gently waved hair for a simple, put together and well groomed look. The chunky boot look was shown to perfection by multiple designers this year – check out some images of New York fashion week to see how the professionals were styling demure maxi dresses in winter season with more masculine footwear to create a dramatic but wearable look.

Best Maternity Maxi Dress


4.      Maternity Black Plisse Maxi Dress

This beautiful black plisse maxi dress ticks all the boxes – first of all, the softly pleated detailing means that as your bump grows, the dress will grow with you. It’s made of polyester, meaning that it is super-easy to care for and its simple, flattering design make it perfect for work, casual or evening wear. To dress it down, just add some comfortable boots, for work add some low mule type shoes and to take it through to evening some bold silver jewelry will add some drama to your outfit. For the chilly winter evenings, you could add a wrap or bolero style cardigan to complete the look, or for a more casual take on the style, a leather biker jacket would give this classic an edgier feel. This would look as good with no make-up as it would with dramatic eyes or lips – it really is that versatile, so you can wear it however your mood takes you. You could work in some of this maxi dresses winter season style by teaming this up with a cosy faux sheep skin coat for the ultimate in winter luxury.  As well as being warm and practical, it’s classic and stylish and will keep out the cold while you look completely on-trend.

Best Evening Maxi Dress

5.      Embellished Chiffon Maxi Dress (£55.00) – axparis.com

This stunning maxi dress from AX Paris gives you plenty of bang for your buck – it’s sophisticated lines and intricate beading make this the ultimate Christmas party dress, but without breaking the bank. As the detailing on this dress is more reserved, you can definitely have fun with your accessories, and this dress would look as eye-catching with a chunky turquoise tribal style necklace as it would with a fine silver chain. Strappy heels are the order of the day with this one – either a co-ordinates black or contrasting silver would be ideal. Complete the look with a similarly beaded clutch bag or purse, smoky eyes and a nude lip. Keep hair simple but elegant with a sweeping up-do and a diamante barrette clip for maximum impact. If you want to stay on trend with this, you could consider a velvet wrap or bolero – these were huge news at London Fashion Week, with Prada and Dries Van Noten both showing models dripping in midnight hued crushed velvet for a luxurious, film star look. If you do go down this route, you might want to think about a statement piece in crushed velvet and a jewel color (such as cyan, fuchsia or magenta). If you are less confident experimenting with color, go classic and retain some mystery with plain black and a delicate beaded fringe – you can find wraps like these in many department stores, and since these particular maxi dress winter season is very reasonably priced for the level of detail it contains, you might be able to splurge on accessories!

Best Knitted Maxi Dress

6.      Knitted Maxi Lounge Dress

This maxi dress from Boohoo even looks cosy – team it with a cute, cable cardigan, thick tights and platform boots for winter walks in the park, or dress it up for work with a tailored jacket and heeled knee highs. It’s another dress that will hold its shape for the day without creasing or looking worn, so it’s also perfect as a travel companion for any trips that you plan on taking. It comes in gray for a more casual look, or black if you’d like it to be more multi-purpose. As ever, these maxi dresses winter season would look spectacular with some statement jewelry – think gold Cleopatra collars or chunky dress necklaces and drop earrings. As with the model in this picture, the dress also looks great with a simple pair of Chucks if you fancy a day shopping in comfort. Keep make-up light and glossy and hair in a messy bun for a carefree style. If you’re looking for a way to bring this look bang up-to-date, try pairing this dress with an over-size mans blazer – this is something that Isabel Marant did to fabulous effect at this seasons shows. It’s not for the faint of heart, however – it doesn’t create a particularly sleek silhouette, so if you’re going to do it go big and go bold. It won’t work with half measures! If you’re not so keen on statement blazers, this will definitely work with a faux sheepskin and some platform boots – these are another maxi dresses winter season that is really only limited by your personal style.

Best Maxi Dress for Petites

7.      True Decadence Petite All over Lace Crochet Maxi Dress with Thigh Split

Maxi dresses winter season can be hard to wear for the petite ladies among us – get it wrong and the lines can make you look shorter and the dress can overwhelm your shape.  It’s best to stick to carefully tailored lines, and tried and tested tricks of the trade, such as the vertical lines in this absolute classic from Asos.  The lines in this beautiful dress will add the illusion of height, particularly when teamed with a pair of sleek heels, and the soft tailoring will ensure that you don’t drown in fabric.  This one is strictly one for the evening, and it’s another one that needs very little in the way of accessories thanks to the heavily ornate lace overlay – it also has a very unusual cut-away section at the back to add interest – all this needs is a thin metallic chain and some discreet earrings to complete the look.  Add height with a glamorous, sleek bun and go for classic, 40’s style make-up – cat’s eye liner and a dramatic red lip will finish this off perfectly.  You could also bring this up-to-date with a luxurious velvet wrap for a bit of additional film star glamour, and replicate looks shown this season by Prada.

Best Plus Size Maxi Dress

8.      Plus Kimmy High Neck Ruched Maxi Dress Winter Season

These gorgeous maxi dresses winter season have a super flattering cut, which will accentuate your curves without clinging. As with all great maxi’s, this is another one that can easily be adapted to take you from morning to evening with some clever accessories and a change of shoes. For casual daytime wear, this would look fabulous with a biker jacket and boots, but you could equally use this for work – all you need is a waterfall cardigan and some dress shoes and you’re ready to go. For evening, you could spice it up with a chunky hammered gold cuff bracelet, smoky eyes and a sleek up-do – strappy heels would complete the look for the complete day to night transformation. You could also use this smooth, sleek dress to play with texture – although it’s not good form to wear the real thing, shear-ling wraps, cardigans and jackets were massive on this season’s catwalks. There are some excellent and very convincing faux versions out there, and you can use them to recreate the look if you’re uncomfortable with the idea of wearing animal skins maxi dresses winter season. If you’re less keen on that idea, go with some military boots, or super-on-trend Chucks or trainers. This would even work with a tracksuit top, so the possibilities for this dress really are endless and limited only by your personal style.

 Best Prom Maxi Dress

9.      A Star Is Born Prom Embellished Tulle Maxi Dress


Yet again, Asos deliver with this stunning Prom dress which is demure yet sophisticated. This dress will allow you to be a princess for the evening with its full, tulle skirt and delicately detailed bodice. As you can see from the model in our picture, this dress is so much of a statement, you will barely need accessories – simple drop earrings are all that is required to complete the look. Wear hair long and flowing and finish things off with some delicate silver heels. Although you could probably recycle this dress after prom for upmarket evening events, it’s definitely one that could be wrapped in tissue and handed down to the next generation – it’s simple, classic lines are ageless and it will look as good in 25 years as it does today. Keep make-up sparing with this one – think dewy foundation, lots of highlighter, immaculate brows and lashes and nude, matte lips. These maxi dresses in winter season is right on-trend too – in fact, stunning and intricate embellishments could be found at Dolce & Gabbana, Gucci, Rochas, Preen, Erdem, McQueen, Moschino and Valentino on this seasons catwalks.  How can that many top level designers be wrong?


Best Casual Maxi Dress


10.  Women Casual Long Sleeve Woolen Blend V-Neck Full Length Maxi Dress Winter for Season


Christmas shopping? Throw on this gorgeous, cosy Maxi, a pair of leggings and some chunky boots or shoes and you’re ready to go. A fake fur jacket or cardigan and thick, knitted snood will complete the look, and you will be able to spend the day picking presents in comfort and warmth. Best of all, these maxi dresses in winter season comes in at under £8 and in multiple colors – you could easily buy one of each for less than the cost of some branded dresses. This one is definitely best for a casual style, but you could dress it up for work at a push – think sophisticated jewelry and nest heels and it could still work. This also comes in plus sizes, which is another bonus feature and (incredibly, at this price) you even get free delivery. You could have one for every day of the week! This is another look that would benefit from nude make up and just-woke-up, messy hair to complete the look. Again, throw on a pair of chunky military style boots to rock one of this season’s big trends.


Best Printed Maxi Dress


11.  R édition Printed Maxi Dress


These beautiful, sophisticated maxi dresses in winter season are perfect for almost any occasion.  Light and flowing, it’s ideal for lunch dates or work, and would look as good with heels or flats as it would with boots. There is a danger of over-dressing this though, so it’s probably best to let the dress speak for itself and keep the accessories to the bare minimum – just a simple, Oxford satchel would make finish this off, perhaps with a chunky cable knit cardigan or tweed blazer. Neutral, bare face style make up will complete the look and you will look like butter wouldn’t melt in your mouth – perfect for meeting the boyfriend’s parents for the first time! To bring this up to the season’s style bar, you could even team this with a vintage velvet blazer in a similar autumnal hue – velvet was big news on the catwalks and it’s sure to translate on to the high street, particularly with Christmas and all of those parties coming up. If you’re not a fan of velvet (and it’s not everyone’s cup of tea), try wearing these types of maxi dresses in winter season with a pair of zip and buckle army style boots – the contrast with this super feminine dress will be incredibly eye catching without being over-the-top.


Best Body-Con Maxi Dress

12.  Burgundy Sexy Backless Hollow Split Back Body-con Maxi Dress

As you can probably see, this one is not for the faint hearten – it’s tight, it’s cutaway, but wow…does it make a statement if you have the nerve to carry these maxi dresses winter season off. This is definitely not a dress that requires accessorizing, as it 100% speaks for itself. For make-up, you may want to think Kim K – mega contouring, matte, nude lips and killer lashes and brows; there is no point in going for anything other than full glamour with this particular number. If you want to adapt it to bring it on trend, perhaps the best thing to go for would be a sequinned wrap – this just won’t work with any of the other significant trends of the season, as it won’t wear well with the bulkier winter items that did so well on the Fashion Week catwalks. You may be able to work it with a faux shearling coat if you are bold enough – then just throw on some strap, platform heels and you’re ready to go with these maxi dresses winter season.

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