Have you ever wondered if you can wear a cocktail dress with ankle boots? Can these seemingly opposite things be styled with each other? Is it a match made in heaven or actually in hell?
Don’t know about you, but I love ankle boots. I usually wear them during the fall and winter months, but I do occasionally pair them with my spring and summer clothes. I love how they look on me, and they provide me with a sense of security.
With them on, I feel like I can conquer the world!
However, I also love dresses. Especially cocktail dresses. For me, they are a perfect balance between formal and informal, since I find it hard to fit into either of those categories.
For the longest time, I have racked my brain trying to determine whether I can wear my two loves together. Would it look good? Would people judge me?
All it took is a few Google searches and a couple of motivational conversations with my mirror image saying, “Oh, just do it already!” for me to finally step outside my comfort zone and try them on together. And once I did, I never looked back. Today, that’s my favorite fashion combination.
If you wish to learn how to style a cocktail dress with ankle boots, I’m more than happy to share my knowledge. Let’s do it!
What is considered to be a cocktail dress?
Do you remember that iconic moment in The Ellen Show when Ellen hosted the main cast of Modern Family? In that episode, Julie Bowen did an amazing impression of Sofia Vergara by retelling their conversation prior to the show.
Julie said that Sofia asked her, in her sassy and exotic Latina accent, “What are you going to wear for Ellen? (…) Is it cocktail? (…) I would wear something tight and like a dolce maybe, but it would have fruit on it or flowers, so you know it’s for the day, it’s not cocktail.”
They then proceed to talk about how Sofia always wants to know if something is considered to be cocktail or not, so she could show up in the right attire. In her words, a cocktail dress would be a dress that’s not a gown but not a sporty-style dress. So, something in between.
And she’s not far from the truth. The term “cocktail dress” was coined by Christian Dior in 1948, and it refers to a business-casual dress, which is a sort of formal piece of attire that has a celebratory feel to it. A cocktail dress is It’s made for semi-formal events which usually take place in the late afternoon or evening.
Usually, dresses that are not considered strictly formal or strictly casual, can be considered cocktail. These types of dresses cannot be too short and too revealing. They also have to be worn with some accessories, like necklaces, earrings, or bracelets, as long as it’s not overdone.
With a cocktail dress, you’re not supposed to carry a huge bag, but rather a clutch, and the footwear you opt for should lean on a more formal side.
Can you wear your cocktail dress with ankle boots?
We have just briefly discussed what actually are the characteristics of a cocktail dress, or of cocktail attire in general. Now, we have to ask ourselves: Can we imagine a cocktail dress with ankle boots? Is that a good combo? Or a bad one?
Generally speaking, you can definitely wear your cocktail dress with ankle boots. These kinds of dresses are usually paired with high heels which do a pretty good job of elongating women’s legs and making the entire outfit appear more put-together.
But, if you’re someone who likes to “think outside the box” and add a touch of rebelliousness to every outfit, then ankle boots can be a great option for you.
However, many people are very opposed to this style. They believe that, by wearing ankle boots, any type of cocktail dress gets ruined, and it loses its original fancy chic.
Those people think that ankle boots, when paired with a nice cocktail dress, make everyone’s legs shorter and stumpier. Which is not a description anyone wants to hear, right?
So, at the end of the day, whether you should wear a cocktail dress with ankle boots depends entirely on your preferences. If you don’t like it, then stick to your trusty pumps or stilettos.
But if you do, then by all means go for it! And here’s a little guide to help you achieve the perfect look.
How to wear cocktail dresses with ankle boots?
1. Consider the season you’re in
First, we’ll start with determining some rules concerning seasons and the type of ankle boots you’ll go for. Bear in mind that these rules don’t have to be blindly followed. However, they can be pretty useful in those situations when you don’t know what to do.
Starting with spring and summer, these seasons are perfect for cute and flowy midi, wrap, or tea dresses with floral or similar patterns. Opt for beige, tan, or brown ankle boots to keep things light and feminine.
Or if you want to wear black booties, make sure the dress you’re wearing is also of darker color to tie everything together.
When we’re talking about fall and winter, choose a layered, skater, or long-sleeve dress with sheer black or skin-toned pantyhose, and pair it with either brow or black ankle boots.
2. What’s the occasion?
You don’t have to have a certain evening event or a guest appearance on a talk show to wear a cocktail dress. However, you do have to think about what’s the occasion like if you want to pair your cocktail dress with ankle boots.
Many people, especially celebrities, can be seen wearing cocktail dresses on a day-to-day basis, managing to pull them off. They do this by toning the whole outfit down with certain accessories and the style of ankle boots they opt for.
If you’re going for a more casual look, you can opt for a nice knee-length cocktail dress and pair it with some western boots. Add a good-old denim jacket or a regular white t-shirt underneath (if the dress is strappy), and you’ll have your perfect casual outfit.
For more formal occasions, opt for high-heel ankle boots. These will give you the height you need while ensuring you look cool and edgy. Top everything off with some expensive-looking jewelry, a neat hairstyle, and a stunning make-up look, and you’ll be the star of the show, for sure.
3. When to opt for high-heel ankle boots?
As we have mentioned in the previous example, high-heel ankle boots are perfect when paired with more elegant and professional-looking cocktail dresses. They give your outfit both the desired edge and femininity.
Personally, I’m a huge fan of black high-heel ankle boots. I feel like they can be paired with everything, from jeans to cocktail attire. They are pretty versatile, and you don’t have to rack your brain thinking about whether they match the rest of the outfit, because black goes well with everything!
A good trick I love to use is to pair a classic arms-length cocktail dress with sheer black pantyhose and black pointed high-heel ankle boots. By doing so, I manage to embrace both my feminine and my edgy side and also make my legs ten times longer than they actually are.
Also, I ensure I’m comfortable the entire time since heels and I… let’s just say we’re not besties.
4. And, when should you go for flat ankle boots?
You’re having a daytime date and want to look innocent and cool? Or you’re going with your friends on a Sunday brunch? For both of these occasions, you’ll probably need a nice dress that’s not too showy, not too casual, and not too mom-like (sorry, mom).
Flat ankle boots are perfect in this case! They are great for your everyday outfits when you want to wear your more informal cocktail dresses with a pair of shoes that are both stylish and comfy.
Imagine this: a beautiful flowy white dress, a causal denim jacket, maybe a nice hat, and a pair of flat ankle boots. Wow! No one can argue that this is the most stylish, but also effortless outfit of them all. If you wear this to a date, you can be sure he’ll definitely call you back.
Who wouldn’t want to see what you have in stock for a rendezvous number two?!
Final thoughts
So, let’s wrap everything up. Can you pair your cocktail dress with ankle boots?
The answer is, undoubtedly, yes! If that’s something you like and if it floats your boat, then sure! Ankle boots can look good with basically anything, only if you’re able to pull it off.
Remember the old saying: “It’s not what you’re wearing, it’s the way you wear it.” These wise words by Pharrell Williams should be your mantra, for sure. Always keep in mind that you’re not the clothes you put on yourself every morning. They are just there to support your inner style and genius.
If your inner fashionista loves ankle boots, then wear those bad boys with your pajamas if you want to. No one can stop you, really!
