Fall is around the corner, are you looking for ideas on how to wear flat booties? I’ve got you covered with the best styling tips for flat booties, cute styles to shop now and tons of outfit inspiration on how to wear your flat booties for the season.
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As a petite woman, I typically opt for shoes with some sort of heel as I like the elongating effect. However, since I have had kids, I have opted for more flat styles as they are just more practical and comfortable for my day to day activities with my girls.
I look forward to the Fall and Winter simply to style boots, and over the last few years I have learned from tips and tricks on styling flat ankle boots that give me the flattering, elongated look I love without the heel height. Here are my expert tips and some current flat boot styles I absolutely love below!
Tips to Styling Flat Booties:
#1 Height Matters – When it comes to wearing a flat boot, you are losing the flattering aspect that a heel brings to the leg. Be mindful of this when choosing the shaft height of your flat boot. A higher shaft boot works well for dresses and skirts, a lower shaft boot works best for straight leg jeans.
#2 Choose the Right Jeans – When styling flat booties with jeans, you want to be aware of the inseam. If you jeans are too long and start to puddle into your booties, it looks very messy and not put together. Finding jeans that hit you on the right spot on your ankle will create an overall more streamlined, cleaner look.
#3 Chunky Soles – Chunky soles add a bit of height and a semi “platform” effect without actually being a heel. This is great if you are on the petite side or still looking for a bit of height to complete your look and elongate
#4 Go Monochrome – When styling flat booties, opt for the same colored bottom to match your boot (example: black leggings and black booties) or even all neutral colors to create an elongated effect
Different Types of Flat Booties:
Black Ankle Boots
Black ankle boots are an ultra classic that can be styled an endless amount of ways.
If you are looking for the best bang for your buck, I would get a pair of classic black ankle boots as you will reach for them often! Suede is always fab but black leather booties are a wardrobe must have!
Brown Ankle Boots
Brown boots always feel more casual and very easy to wear. I love the suede styles but also love a cognac leather style for a classic brown ankle boot.
These are the best ankle boots to style with a cute floral dress and a suede moto jacket for a lunch date outfit!
White Ankle Boots – White boots are trending and I absolutely love the suede styles as they feel a bit softer and can be worn day to night.
Stark white boots are fun and I also love more earthy white boots in a bone colored hue that feel effortless to style. With this color they even work for warmer weather and summer dresses!
Combat Boots
Combat boots are some of my favorite flat boots to wear! I love the edgy feel they offer to any outfit and how comfortable they are.
You can style them with dresses just as easily as you can with denim. There are so many options when it comes to combat boots today, they have them in black, brown, red and even bejeweled options.
Chelsea Boots
Chelsea boots are a specific style of boots with an elastic sides and ankle height shaft. They are extremely comfortable due to the stretch with the elastic and the common chunky heel detail.
Chelsea boots are not only comfortable but they are a very neutral style that works well with all different kinds of outfits and styles. You can pair a floral dress with Chelsea boots or black skinny jeans, and both look great!
I love these nude suede Chelsea Boots!
Cowboy boots
Cowboy boots have started to become more trendy in the recent years and although they may not be your day to day boot, they are a fun style to mix things up and you can find some really great flat/low heeled styles that are just as functional as they are fashionable. I love the color of the option below as it pairs nicely with all different colors.
Knee High Boots
Knee high boots are another classic favorite, such as the riding boot style I linked below! They have a bit of a preppy aspect to them that I think looks really chic and clean paired with a cute dress or a great pair of denim.
Knee high boots also look great with maxi skirts and dresses that have higher slits on the side for a really chic and effortless polished look.
Over the Knee Boots
Over the knee boots are one of my absolutely favorite styles of boots! I love the heeled versions but the flat versions are just as good and are extremely comfortable to wear.
The over the knee boot hits on the thigh and is perfect to extend the wear of your shorter skirts and dresses in the colder months. I love them paired with black tights and faux leather leggings and an oversized sweater for Fall.
Shop these flat over the knee boots here
Pointed Toe Boots
A classic pointed toe ankle bootie is one of the most flattering boots you can wear! The pointed toe really elongates your leg, and especially if you style it monochrome (example: black boots and black leggings) your legs instantly look longer and leaner.
I opt for pointed toe styles in most of my boots as even when they are flat in height they are still so flattering.
Wardrobe Essentials To Wear with Flat Booties
Boyfriend Jeans
Boyfriend jeans are a go-to for me year round. I love the effortless feel, the distressing and the comfort level is key. I love styling my flat boots with boyfriend jeans and a blazer to run errands, grab lunch and go to meetings during the week.
This is an easy outfit that is so comfortable that also looks SO chic and put together. Opt for a boot with a lower shaft height so that you don’t have to tuck the excess fabric at the hem into higher boots.
I am always looking for ideas to style different wardrobe essentials as I love creating capsule wardrobes and streamlining my closet.
Most of these outfits are based around items you likely already have in your closet that will look SO cute styled with flat booties or really even booties with a stiletto heel if you want to have more options!
Neutral sweater
You can actually wear this outfit in a number of ways, with skinny jeans, leggings or even a skirt! It’s a cute and simple way to pair with booties and one of my go to looks for fall!
Black Tights
I absolutely love pairing black tights with flat booties as they work with every single style of flat booties. You can style black tights with ankle booties or with over the knee boots and it looks so flattering and is weather appropriate for the colder months.
Related Post: 15+ DRESSES TO WEAR WITH KNEE HIGH BOOTS
Mini Skirt or Mini Dress
Mini skirts are a favorite of mine although I understand a personal preferences if you are taller or have longer legs. For me, the shorter length always works well on my petite frame.
I love to pair flat boots with a mini skirt as I don’t necessarily like a higher heel height with a shorter length skirt/dress, the lower height makes for a more comfortable outfit overall and can really flatter the leg.
Chelsea boots or pair of ankle boots paired with a mini skirt but also love the look of over the knee boots with a mini skirt or a mini dress like I’m wearing below.
Black Leather Jacket
A black leather jacket is a true staple in my wardrobe throughout the Fall/Winter and I can’t wait to bring it out once the temps drop!
A black leather jacket is a no brainer when paired with flat booties, as they both bring an effortlessly cool element to any outfit. For a different ways, pair it over a dress or with a white-shirt and jeans with a killer pair of combat boots for a total chic look.
Puffer jacket
Living in the pacific northwest, I’m a huge fan of the puffer jacket and they totally work well with ankle boots! And if you know me, I live for mommy and me outfits so I got matching boots and jackets for me and my daughters!
Pencil skirt
Pencil skirts are flattering on all body types and a great classic look. You can even style them for the work environment with a flat bootie.
When it comes to pencil skirts, you want to be mindful of the flat boot you choose and the shaft height, as the midi length of the pencil skirt can clash or cut the leg if it does not hit in the right spot.
Black skinny jeans
Black skinny jeans are the best way to go casual and chic. Skinny jeans and black jeans are always flattering and work well for so many different occasions. Whether it’s classic ankle booties or knee high boots, I think flat boots paired with black skinny jeans looks so sleek!
This is a definitely an outfit where I would pair black boots with the black skinny jeans to really elongate the leg. This also works with blue skinny jeans if you don’t have black jeans in your wardrobe.
Oversized Sweatshirt
This is my easy mom outfit for all our outings! A cute sweatshirt, skinny jeans and flat boots. These are a bit higher up on the ankle so they provide a lot of support especially when I have to carry and chase after my little one!
Black dress
A black dress is a classic wardrobe essential that you likely already have in your closet! Whether its a body hugging black dress or a cute shift dress, flat boots are an easy option to style it up! It’s classic when worn with high heels, but a pair of black booties make it an updated twist!
I love the look of cool combat boots with a simple knit black dress for day, or a chic black shift dress with suede over the knee boots for date night.
White Blouse
A white blouse for the fall is so easy to style and look so pretty for all occasions! A classic white sweater can pair with all different kinds of bottoms, which makes for the perfect pairing to flat booties!
An easy outfit idea is to have your sweater tucked into the plaid skirt or a flowy blouse like this paired with skinny jeans.
White T-shirt
You can never go wrong with a crisp white t-shirt! You can pair them with jeans or faux leather leggings and a great chic blazer as seen below.
This is the perfect canvas to pair with your favorite pair of flat booties or different types of boots! You could also pair a simple white t-shirt with denim and cowboy boots for a more casual look.
Midi Dress
Midi dresses are super flattering and are another great option to pair with your favorite flat booties. I really love the look of knee high boots with a midi dress, and I also think combat boots are a fun contrast!
When it comes to styling a midi dress, if you are choosing a flat boot with a higher shaft height, I would opt for a pointed toe style.
Floral Dress
Floral dresses are another piece for me that I wear year-round, and styling them with flat booties instantly makes them Fall appropriate!
You could easily pair a summer floral dress with tights and combat boots, or a maxi floral dress with knee-high boots. The options are endless and I love the contrast between the feminine florals and more masculine/edgy boots.
I love to look at Pinterest for outfit inspiration (if you are a fellow pinner, follow me here!) The amazing outfit ideas above are some that I have found on Pinterest and am definitely planning to recreate this Fall/Winter.
Here’s a look that I wore with a floral dress and tall flat boots. I find that long dresses are great for so many shoe options!
If you love these ideas, pin the image below to your board to refer back to this post!
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