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!
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?!