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Ankle boots are the perfect footwear to transition from summer to autumn or to add a more casual touch to any outfit. Since these boots are so versatile, they can be worn with any piece of clothing, including dresses. On the other hand, each type of dress requires a different way to wear your boots, to make sure that you can properly rock every part of your look.

If you have ever wondered what is the best way to pair your favourite ankle boots with your dresses, you are in the right place. We have finally found all the best secrets from the most famous influencers and fashionistas to create some of the most glamorous outfits with the pieces you may already have in your wardrobe.

From midi dresses to Western boots, here you can get inspired by some of the best ways to wear your dress and ankle boots in winter. Ready to be the star of the next Wintertime with your fabulous outfits?


How to Wear Ankle Boots with Dresses

There is no such thing as standard ankle boots. In fact, you will find dozens of types of footwear on the market, based on the shape of the toe and the length of the heel. Some of them are comfortable and cosy, while others may be more elegant but not the best choice if you intend to dance or spend much time standing on your feet.

Of course, when it comes to pairing your ankle boots with your dresses, you are free to choose the styles that you think look best together. On the other hand, there are a few tips we want to share with you to help you create the perfect look and make your life easier.

Experienced fashionistas advocate that the best boots to wear with dresses are tall shafts with a pointed toe. With their shape, they elongate your legs, making the entire look balanced. However, you can also rock your outfit with some rounded toes and shorter shafts, also depending on your silhouette.

If you are creating your work outfit, then you should try with leather booties, which usually look nicer and more elegant. Pointed-toe leather ankle boots are also comfortable when worn for many hours, and are great with any weather.

How to Choose the Right Dress Length for You

Dresses are some of the most versatile pieces of clothing, especially when it comes to pairing them with your favourite shoes. However, you cannot just pick up any dress. In fact, depending on the season and the occasion, you might need to wear a piece with a certain length.

Maxi Dresses

Maxi dresses always have that nostalgic feeling that makes them cute and lovely. However, there are several ways to adapt them to your modern style, even if you usually prefer bolder looks. For example, they are perfect when paired with a leather jacket and a pair of heeled ankle boots. For the best results, add a coordinated clutch.

Midi Dresses

Midi dresses have the power to enhance any silhouette, making you look immediately slimmer and taller. The skirt of these dresses is in a mid to heavy weight, meaning that they hang naturally on your frame and highlight your legs’ shape.

The best way to wear these pieces is with an oversized blazer or leather jacket. When it comes to shoes, experts recommend going for heels rather than flats.

Otherwise, the skirt length may make your calves and lower body look wider if not balanced adequately. The right pair of ankle boots will elongate your frame, and pull the whole look together fabulously.

Mini Dresses

Who says that you can’t show your legs off in winter? Mini dresses are perfect on any season, including when the weather is too cold. These pieces are a great option for both tall and petite girls, as they can elongate your legs if you pair them with the right shoes.

To enjoy your mini dress, you can pair it with a polo neck sweater, to layer different pieces and create a winter-proof outfit. Alternatively, pair a floral mini dress with some heeled ankle boots and a leather jacket for the perfect rocker vibes.

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Should I Wear Leggings Under My Dress?

When the weather is cold, a pair of leggings can make your life easier, and allow you to wear your favourite dress and a pair of ankle boots without freezing.

However, we shouldn’t forget that leggings are part of the accessories we use to enhance our look. This means that we should choose the best pair to match our outfit.

Besides, when worn properly, leggings can make your body look slimmer, and create another cool and colourful layer of clothing between your dress and your ankle boots.

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How to Wear Leggings with Dresses and Ankle Boots

The length of the dress you want to wear will influence not only the style of your ankle boots but also the pair of leggings you should choose to create your look.

Short to Mid-Length Dresses

Usually, shorter dresses are the ones who work best with leggings. This is the best way to show off your legs, without being too cold. If you are wearing a cute, floral mini dress then you should opt for total black leggings.

Avoid white and other light colours, as they won’t make your outfit look dull. Similarly, with black or monochromatic dresses, you are free to play with different colours and patterns to make your legs stand out from your silhouette.

Knee-skimming Dresses

Knee-skimming dresses and ankle boots are always challenging to be paired together, as they may make your silhouette look bulky. However, with leggings, you can immediately sort this problem.

They will give your outfit a fun and bright moment while creating an additional layer to diversify your body shape. Besides, this can be a perfect overall style to update your workwear in winter and keep yourself warm, cosy, but always fabulous.

Maxi Dresses

When it comes to maxi dresses, wearing leggings or tights is usually something you would do to keep yourself warm. In fact, although they are perfect for extra warmth, they don’t add much to your outfit in terms of style, as they will most likely be hidden under your skirt.

However, this doesn’t mean you shouldn’t be wearing your leggings if you feel like it. Don’t forget that the main rule of fashion is to enjoy one’s outfit and wear the pieces we feel most comfortable with!

Heel & Toe: How to Choose

If you are a tall girl, then you should prefer a pair of ankle boots with a block heel, which will enhance your ankles and legs. However, kitten heels still have a minimalist vibe that we all love.

When it comes to the shape of your ankle boots, the square toe is a versatile style, always used by high-end designers because it gives space to add embellishments to your footwear. It is also very comfortable and makes it easier to walk even with the highest heel.

To make sure to find the best pair of ankle boots for you, we recommend trying different styles, also keeping in mind which kind of dresses you wear more often. It is vital to invest in a good pair of footwear, in suede or leather, which will last for many seasons!

Embrace the Cowboy Look

Pick your favourite long-sleeved dress and pair it with a comfy pair of cowboy ankle boots: you will have the hottest cowboy look! To make the look perfect, don’t forget to:

  • Wear a colourful dress, with a belt on your waist to highlight your silhouette
  • Avoid wearing any tights, it’s time to show your legs!

Printed Tights

Your legs can be your best accessories to complement your dress and ankle boots if you play with the right pair of tights.

  • Opt for sheer black tights with a subtle print for a glossy look
  • Go bold and rock a pair of printed leggings to create a statement outfit

Chic & Cosy

One of the best things about getting ready on wintertime is that you can layer more pieces of clothing to stay cosy and comfy. To keep your legs warm and look chic, you can wear:

  • A mid dress. Prefer natural colours, such as brown or taupe.
  • Your ankle boots.
  • A pair of warm tights, which should be the same colour as your boots.

Metallics Are Your Best Friends

Metallic ankle boots are perfect to lift darker outfits and add a touch of colour to any winter look. You can play with different shades and colours. Just try to avoid wearing other bright accessories if you want to keep your style elegant. Otherwise, if you like bolder options, you should definitely pair different metallic pieces.

Lace-Up Boots Made Simple

Lace-up boots are some of the cutest footwears you can wear, especially if you are creating a work outfit or you are looking for a chic style.

You can mix & match different patterns and fabrics, such as suede or leather, to completely change the tone of your look. Even a pair of biker boots can look classy and elegant, with the right dress!

Combat Boots and Cute Dresses

Combat boots are always the best choice when you feel like embracing a rock look. However, with the right dress, they can become pretty versatile and be worn even when spending the day at the office.

Dr Martens is only one of the many brands offering different styles of combat boots, to give you a wide range of possible outfits to suit any occasion and, most importantly, your mood.

Contrast with Denim

Ankle boots are usually paired with jeans and denim clothes. This means that they will look great with your favourite denim dress. Add some cosy tights to give the whole look a wintery vibe, and to balance your silhouette. This will great a London-girl look which will make you the star of any winter day.

Also Read:

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How to Style Denim Dresses (Women’s Edition)

Faux Fur & Animal Print

No look is too bold if you love it and you feel comfortable when wearing it. If you like to experiment with different patterns and textures, then you should go for snake and other animal prints. Make it a statement outfit by layering a faux fur coat, in a contrasting colour. Everybody will be staring at your fabulous style!

Also Read:

How to Style Leopard Leggings…

Sweater Dresses

Sweater dresses are lovely and cute. However, you should always pair them with some accessories to enhance your silhouette and avoid the pyjama-like look. We recommend:

  • A mid sweater dress. Go for warm fabrics, such as wool or cotton.
  • A pair of ankle boots.
  • Your favourite leggings. You can either choose a natural colour or rock a bolder style.

Also Read:

How to Dress a Sweater and Skirt Outfit This Fall – Outfit Ideas & Styling Tips

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Update Your Office Wear

Bring your favourite ankle boots with you even at your office, with a classy and easy look. All you need is:

  • A mid or long dress. You can go for total black, or add a few details to make it more colourful.
  • A pair of cosy tights or lightweight leggings.
  • Your ankle boots. Make sure they are comfortable enough, especially if you have to spend some time on your feet.

Also Read:

How to Look and Feel Like a Boss: The Office Styles of the Eighties (Women’s Edition)

Bold Leather to Rock your Wintertime

Leather (or faux leather) is the perfect fabric to embrace a rock outfit. Most importantly, it will keep you warm and it looks perfect with any type of ankle boots.

Also Read:

How to Style Leather Jackets (Women’s Edition)…

Go Black, or Go Home

Total black is a timeless classic, which looks good in any situation. Mix & match all your black pieces for the perfect classy look. Don’t forget a pair of big sunglasses and a long necklace to make your outfit brighter.

Layering Is the Key

Even in winter, you can wear your favourite sleeveless dress if you layer it with a warm jumper or shirt underneath or over it. Just a few recommendations:

  • Play with different fabrics and patterns, so your silhouette won’t look bulky
  • Choose a pair of tights which colour matches that of your dress.

Match Your Accessories…

The secret to creating the perfect outfit is to match all accessories. This means that you should try to match your ankle boots with your bags, belt, jewellery, and any other piece.

…Or Play with Different Styles

On the other hand, you can express your creativity by playing with different fabrics and patterns. If this is your favourite look, just avoid wearing too many pieces of accessories, as you want to focus the attention on your boots and your dress.

Rock Your Best Accessories

Winter is the perfect time to rock your favourite scarf or beanie hat. When you pair your dress and your ankle boots, you can decide to wear a single piece of accessory in a bold pattern or colour, to focus the attention on it. For example, try with a bulky red scarf.

Highlight Your Shoes

If you want your ankle boots to be the protagonist of your outfit, you should go for a bold pair to be worn with a simple, natural-coloured dress. Of course, you can add a pair of cosy tights and a simple belt, to build a slimmer silhouette.

Long Dress, Slim Silhouette

Long dresses are underrated. With the help of a pair of ankle boots and a long coat, they can immediately make your silhouette slimmer and taller. Try to match all dark and natural colours for a better result, and don’t forget a bulky bag to make them look bolder.

dailymail.co.uk - Gigi Wearing black long coat with black sunglasses, black dress and black ankle boots
Source: dailymail.co.uk

Black and Blue? The Perfect Match!

Many believe that black and blue pieces of clothing should never be worn together. However, this isn’t true. In fact, a pair of black ankle boots will highlight the blue of your dress, making all colours brighter and giving you a classy and chic aura.

Don’t Forget Your Hat!

The best way to make your look bolder is to play with your accessories, including hats. A wool fedora hat, especially if it matches the colour of your ankle boots, will immediately make your outfit more stylish, and keep you warm.

Also Read:

How to Wear Hats – What Hat to Wear With Your Coat – Women’s Edition

Make It Bright and Colourful

The best thing about ankle boots is that they match perfectly with any colour. To embrace your wintertime vibes, you can wear a yellow sweater dress or a colourful wool coat. Keep your accessories neutral if you want to look chic and classy.

Also Read:

How to Wear Neon Colours…

About The Author

May is totally crazy about the 80s and everything the decade inspired! Having grown up in a household that was totally taken over by 80s music and fashion its only natural that May lives and breathes the 80s!

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