Casual Shoes & Boots for Fall: 20 Stylish Pairs Under $100

Fall is just around the corner, and that means it’s time to put the flip flops away and move on to some more fashionable (and less beach-appropriate) fall footwear!
Last week we talked about footwear trends for fall 2009, but as we all know, trends aren’t for everyone! There are plenty of amazing casual shoes out there that don’t conform to any particular trend. Even though they aren’t technically “trendy”, the following shoes are all in style and fabulous for fall.
Here are 20 amazing fall shoes and boots you’ll want to wear everywhere: from your 9AM math class to your 10PM study date. These shoes deserve to be seen! Even better, at $100 or less a pair, they won’t kill your budget.
Ballet Flats Under $100:
The ballet flat is a total classic. Worn with skinny jeans, a pretty dress, or even shorts, it always comes off as effortlessly stylish, classy, and appropriate. You can thank Audrey Hepburn for that!
There are SO many cute flats out there right now – it was incredibly hard to pick my top 5 pairs under $100!
I finally decided upon a diverse mix of different styles to fit different tastes. Neon flats for an 80’s throwback, simple grey faux Ferragamo bow flats, printed flats in plaids and florals, and finally (my favorite pair), ultra-embellished Calvin Klein flats with a super cute metallic detail on the toes.

Product Information (clockwise from top): Patent Ballet Pumps – Newlook.co.uk, Bow Tie Canvas Flats – Charlotte Russe, Very Volatile Abbey Lane Flats – Piperlime, BKE Sole Flower Shoe – Buckle, Calvin Klein Mackenzi Embellished Flats – Piperlime
Cute Sneakers Under $100:
I’m not a sneaker fan myself but I know lots of you walk EVERYWHERE and love your sneakers. I know I’m never going to stop you from wearing sneakers, so if you’re going to wear them, might as well get yourself a cute pair!
Here are five stylish sneaker options: from classic Converse All-Stars to old-school Keds, you can’t go wrong with the basics. I also threw in a couple fun pairs of Nike Dunks because I think they’re fabulous when worn with skinny jeans and plenty of attitude. Which pair is your favorite?

Product Information (clockwise from top): Lace Up Tennis Shoes – Wet Seal, Converse OX in Teal – dELiA*s, Nike Dunks – Pickyourshoes.com, Converse All Star Chuck Taylors – Zappos.com, Nike Dunk Low – Nike.com
Mid-Calf and Knee-High Boots Under $100:
While over-the-knee boots are definitely the footwear trend of the season, boots that hit below the knee aren’t “out” by any means!
I thought it would be extremely tough to find a cute pair of boots under $100, but I was surprised to find plenty of options, many even real leather! Most of my picks are from Piperlime – they have an incredible selection right now. From suede options that would be great with a dress and tights to rocker-fabulous buckled boots, there’s an affordable pair to fit any style.

Product Information (clockwise from top): Very Volatile Date Night Boots – Piperlime, Nine West “Frolic” – Piperlime, Rocket Dog River – Piperlime, Unlisted by Kenneth Cole “Saddle Up” – Piperlime, Star Ling “Julian” Flat Boot – Nordstrom
Ankle Boots Under $100:
The ankle boot was HUGE last year, and it’s still lingering in stores. Cute with skinny jeans, tights, and even alone worn with a dress, ankle boots are fabulous, versatile, and the ultimate in comfy casual.
Depending on your personal style, there’s an ankle boot out there that’s perfect for you. Studded, buckled options in black leather or suede give off a badass vibe, while simple slouchy brown leather is very boho chic. There’s always plain black as well if you just want to keep it simple and let the rest of your look shine.

Product Information (clockwise from top left): Xhilaration Kandace Ankle Boots – Target, Bamboo Tinker30 Ankle Boots – Cutesygirl, Rocket Dog Rosebud – Piperlime, Gambia Slouchy Boot – Forever 21, Black Suede Studded Ankle Boot – Dorothy Perkins
Your Thoughts?
You’ve seen my picks for casual fall footwear. Now I want to know what you think!
What’s your favorite pair of shoes to wear during the fall semester? Are you a ballet flat kind of girl or do you prefer to wear boots in the fall? What do you think about sneakers? Leave a comment below!
Posted on on August 25, 2009 / Filed Under: Shopping / Tags: Boots, Flats, Flip Flops, Neon, Shoes, Shopping, Sneakers, Trends
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melanie
LOVE those neon yellow flats! as rachel zoe would say, “i die”!!
Brittany
I love the ankle boots. I like that that the studded and buckled ones give off a bad ass vibe like you said. I would definitely buy the ones from Cutesygirl.
Anna
I wear boots throughout the fall. Last year I wore black leather boots every day pretty much, and I just bought a pair of brown faux leather boots (only $50 at 344) that look cute with jeans.
Meghan
great post. i need some new boots to pump up my wardrobe for the Fall. just got darling booties from charles david though!!
anthea
Great post! I wear ballet flats a lot but love a great pair of boots. I wore cowboys a lot last year but am on the look out for something a little different this year. Perhaps some ankle booties!
www.abbie-thewriter.blogspot.com
I want some slouchy ankle boots!
Annie
I’m such a sneaker person because I walk so much, but come winter, I wear knee high boots almost every day. It’s raining/snowing all the time here in Canada, and if not there’s water/snow on the ground anyway.
I’m a real big fan of oxford booties, hope those are still in, they’re like an amazing heel/ankle boot combination! Hard to find a good quality pair that’s closed toe (otherwise it’s impractical) and a good price though…
Btw I love those white/flower/print flats!
Erin
I LOVE the ankle boot trend, however I’ve been waiting out the past couple years for the right pair. I think I finally found them from the brand Blowfish, of all places. My biggest requirement was that it have about a two inch heel (leg lengthening but I can still walk everywhere) and for some reason that seemed impossible to find!
Anyway, for any of those girls having trouble with the ankle boot heels, check out Blow Fish brand for some pretty ankle boots. I got the Willis in black, and they’re available at DSW for $70 and free shipping at the moment.
http://www.dsw.com/dsw_shoes/catalog/product.jsp?index=2&category=&prodId=179292&brand=300058
Luinae
I have a pair of falt below the knee boots almost exactly like that pair from Nordstrom, but mine were from a charity shop. And I’ve finally found the PERFECT pair of ballet flats, really comfy and cute and stylish. I love Audrey Hepburn, she was so right about so many things!
Jennifer
I’m buying at least one of the flats, sneakers and ankle boots – though not too sure about the other boots. If only I could afford more than one pair of each though . . . one day when my college education gets put to use through a good job!
Alana
The ones from Forever 21 are totally sold out I tried buying them a few days ago. I’m still trying to find a pair that I love just as much.
Charlotte
I can never find ballet flats that are comfortable for walking a lot! None have enough arch support for me- flat shoes–> fallen arches and flat feet!
ReneƩ
Great post again ! Love all of’ them but especially the ballet flats and knee-high boots ! I’m looking for them everywhere in these days hope I’ll find my perfect pairs :)
Hazy
I love those neon ballet flats, but the website doesn’t ship to Canada :(
Has anyone noticed a similar shoe that might be available in Canada?
Alesha
Hazy I saw a similar pair at Forever 21 a while back.. Zephyr talked about them on her Twitter! Maybe they still sell them??
Ashley
I really love ballet flats, but they are kind of painful to wear all around campus. I did like your sneaker selections, but I LOVE my kangaroos! (Neon, slim profile, and oh so hot!)
Personally, I don’t like ankle boots because the ankles are the smallest part of my leg, and if I cover that up, I’ll look like I have tree trunks for legs!
stephanie
just to add something. i was recently in k-mart and i sw some extremely cute piper and blue flats for 9 bucks! and kohls has the ankle booties for like 15 bucks. just wanted to let people know
Kate
i love the neon ones!
on and anyone looking for shoes, at Charlotte Russe there’s a buy one get the second pair for $10 sale going on, and lots of cute flats and boots!
shreyashi
i loved the boots i would love to buy them
Maxine
With my big calves, boots are just trouble waiting to happen. I’m a sneakers type gal, I love flats but being 5′1 I need some height. My top choices would be the nikes and the knee high boots. I’ll wear them with skinny jeans.
Nat
& what about skirts? in the list they were after dresses..
Ashley
Hi Z, this is a good post but i was wondering if you could write a “How To Wear Ankle Boots” feature. I just got 2 of them from cutesygirl and i could use some help. please and thankyou.
Veronica
I agree with Ashley! I just got a pair of ankle boots from target and am not sure how to wear them! With winter right around the corner I think a “How to wear Ankle Boots” article with outfit ideas would be great! Thanks!