How To Wear Ankle Boots
Boots have always been “my thing”. I was the girl being made fun of because I wore boots with everything when it wasn’t cool to do that yet. Seriously, I wore boots with fancy dresses, casual dresses, long dresses, & short dresses. I wore boots with jeans. I wore boots with leggings. Truly I thought of all the ways to wear booties with everything…and honestly, I still do. My family would always look at me like “are you sure?” and then they’d end up loving it and a few months later everyone else did too. If you’re interested in learning a few tips for styling outfits with ankle boots that I’ve learned along the way than continue reading below.
Different Ankle Boot Styles
For a boot lover like me, we are so lucky because there are SO many different popular ankle boot styles these days. There’s different shapes, heel types and there really is something for everyone now and for every occasion. In my opinion, there are five ankle boot styles that are most popular this season: 1) rounded toe metallic or glitter boots, 2) pointy toe black booties, 3) colored ankle boots, 4) sock booties, and 5) combat boots.
Another trend with ankle boots this season is heel types. In the past, there used to be a specific type that was considered cool. For example, when 6 inch heels were trendy, kitten heels were considered ugly but now every heel type seems to be popular which I love. Not only do I personally love all different types of heel types, but that means that there really is a shoe for everybody. The important part is now though — how do you style these trendy must have boots?
Ankle Boots With Dresses
Ankle boots with dresses is a favorite of mine, but picking the right one is super important. Wearing boots with dresses is so cute to do but can be tricky — the boots can either make you look really short and not super flattering or it can be amazing and elongates the leg. I have found two boot trends to be particularly flattering for this type of a look. I love a pointed toe bootie or a sock boot.
With these two styles, I feel like you’re options for what dress to wear opens up and you really can wear anything + you can easily put black tights or patterned ones for a completely different look. I love the idea of a pointed toe flatter bootie with a mid length dress or a pair of sock boots with a mini dress. Both of these boots are interchangeable with the looks and really cute options.
Ankle Boots With Jeans
Jeans are probably the easiest ways to wear booties. This season I wanted to find a pair of colored ankle booties and glitter or metallic ones that were great for styling Fall outfits for when it’s not cold enough to pull out your over the knee boots. Both of these style of boots look amazing with skinny jeans (pricey but best fitting jeans), a dress, or a wide leg jean (affordable and so cute) like I’m wearing in the photo below.
How To Dress Up Ankle Boots
Often times people think you can only wear ankle boots with a ripped up casual pair of jeans and a t-shirt. However to me, ankle boots can be worn for so many more occasions. Ankle boots can be a more dressed up look for a slightly fancier occasion if you style it correctly and can also be styled really well for a business casual look, which is my personal favorite. When I worked “normal” or more traditional jobs, I always struggled with what to wear.
I was so sick of wearing heels everyday. Especially because my first job in retail required me to wear heels everyday and I stood in heels on marble floors for 8-9 hours a day #torture. After that, I was over it. The excitement of heels had been lost and I needed a comfortable but appropriate alternative. In that time, I learned how to dress up ankle boots. From that, I expanded and came up with ways to dress up ankle boots not only in the work space but also outside of it. I had to go to go to outfits that I came up with for each occasion.
Outfit #1: The Dressed Up Ankle Boot (General)
Styling a look with one color story helps pull an outfit together and sometimes even gives the illusion that the outfit is dressier than it is because you are so well put together and it is well thought out. This outfit is the perfect example of an easy outfit that really isn’t so dressed up but somehow seems more put together because of the brown/neutral color story I have told here.
Outfit #2: The Business Casual
This outfit allows you to not only wear jeans but it also allows you to wear a black t-shirt. By choosing plain washed black denim with no rips and a long sleeve solid black shirt, this combination already looks nice enough and appropriate enough for work. By adding a blazer and metallic booties, this outfit feels more styled complete. It shows that you tried to get ready and put effort into your look but allows you to still be comfortable and wear boots to work.
Brands That Make The Best Ankle Boots
Brands that make the best ankle boots?! This is such a hard question to answer because I truly have SO many. I guess if I looked in my closet I would see a pattern though of which brands I lean toward for ankle boots, which I guess would make them “the best” in my opinion. 10 brands that are “the best” in no specific order:
1) Steve Madden – I swear Steve Madden boots last me forever. I have one pair that is the same pair I’ve had since my senior year in high school.
3) Sam Edelman – affordable and good quality + always on trend
4) Gianvito Rossi – my love! So creative and amazing + the comfort of his shoes is incredible! I own two ankle booties from him and I live in them. The Mackay (photograph doesn’t show the color correctly…olive green in person and amazing) is my personal favorite out of the ones I’ve tried so far because I can walk miles in them and complimented everytime plus I love how he is a designer that is not overly trendy.
5) Topshop – consistent and well priced. I go up a 0.5 size in all of my boots from them but they are always really comfortable. My red boots that I’m wearing in these photo’s are actually from there and they are AMAZING. I walked 5 miles in New York in them and could have walked 5 more.
6) Chanel – who doesn’t love Chanel? Chanel definitely runs 0.5 size small, or at least on my foot, but otherwise I am a big fan! I definitely recommend trying on a pair in person before purchasing though because I know Chanel boots are not comfortable on everyone. For example, on my foot they are great but my mom can’t wear them.
7) Kendall + Kylie – one of my favorite brands right now. I am obsessed with them ever since I wore a pair of their booties to NYFW this past February when there was a crazy snowstorm. I, of course, packed the worst shoes for a snow storm and went around town in a heeled pair of velvet booties. To my surprise, these boots ended up being AMAZING. First of all, all of their shoes and line are so cute but they are so comfortable and durable. These VELVET boots were not phased by the snow and I still wear them all the time.
8) Stella McCartney – I just love her line and what she stands for. Period. Everything she does is unique and cool. Her line is super expensive but it is so awesome.
9) Stuart Weitzman – I have been wearing Stuart Weitzman in some way since I was a little kid. Stuart Weiztman is one of my mom’s favorite brands ever so I’ve been going into her closet since I was little and playing dress up with her fancy shoes. I love how timeless they are, yet they always keep up with the times in their own way.
10) Dr Martens – Dr Marten have been around forever and for a reason. They are practical, durable, comfortable, ugly but in a cute way, edgy but in an oddly classic way + they are super affordable compared to other brands. Everyone needs to own a pair of Dr Martens at least once in their life!