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  • Writer's pictureKyrstyn Hokey

7 Pairs of Shoes You Need to Get through Fall (Too Many?)

Updated: Sep 18, 2020

1. Ankle Rain Boot

There's no getting around the rain in fall. Where there's rain, there's mud. And where there's mud...there's a broken heart over ruined shoes you shouldn't have been wearing in the mud. Do yourself a favor and get these rain boots! They're so cute and go with so many things.

I personally have the Sam Edelman "Tinsley" ankle rain boots in black, and I practically live in these every fall. They're getting worn out from all the use, so it might be time for a new pair this year! The best thing? When they get muddy, I throw them in the shower and rinse them off with the shower head. They dry in there, too!

2. Over The Knee Heeled Boot

Color suggestions: Black AND Taupe, but black first.

These make your legs look a mile off the ground when worn the right way. If you can, get them in black and taupe. If I had to choose one color, I'd have to go with black as much as it hurts my heart to have to choose. The best thing you can do for your height is to wear black leggings or skinny jeans with these.

My dream pair of over the knee heeled boots come from Stuart Weitzman, but if you're not wanting to spend $400-$800 you can find so many others that will fit the bill.

But please, please, please...don't get a cheap looking pair. You don't need that kind of negativity in your life, honey.

Invest in boots that stay up when you walk, that have sturdy shafts, and that don't fall to your ankles when you sit down and get up. You'll be pulling those boots up all day long, and, frankly, we're tired of seeing it. Try them out before you buy. And if buying online, return those bad boys if they're not behaving. You'll have some slipping with any boot, but whether that's a small slip or an avalanche is up to the quality of the boot itself.

3. Heeled Ankle Boot

My color suggestion: Taupe

I very much think they're a staple. You can wear them with so many things, and they'll fit the bill for weekend casual.

Not only do they add that length to your leg with the color, but also with the pointed toe. Ladies, I nearly always suggest a pointed toe on whatever boots or dress shoes it comes on. It adds length to the legs. Sometimes almond, but never ever rounded (I might make some enemies saying that). We 5'5"ers need as much leg length as we can get, and rounded toes just aren't doing it for us! If you're tall, sorry, I still don't like rounded toes. But again, that's just my opinion. Kill it in whatever toe style you like the best!

4. Riding Boots

My color suggestion: black AND brown, but brown first.

The heel height is up to your preference. I personally like to have a little extra height, but I also would wear riding boots with little to no heel. This is left to you to decide what works best for you, where you live, etc...

Obviously, if you're actually going to be riding in these, then opt for the flat ones!

Make sure that you get them in a tone that matches a belt and bag you have. It won't look nice to be wearing brown boots, a taupe belt, and a cognac bag all at the same time. Know your colors, the differences, and what looks best on you.

5. Pointed Flat or Loafer

Color suggestions: nude AND black.

For those occasions when boots are too casual and heels are too cumbersome, these flats have your back. I have my eye on "The Point" flats in Ecru by Rothy's right now!

Flats are some of the easiest shoes to buy affordably without looking cheap. A $20 pair of flats, if in good condition, can easily look as good as designer-made flats. However, when they start looking worn, time to replace! Nothing looks worse than a worn out pair of old flats. Shudder.

6. Pointed Stiletto High Heel

As classy as they come! Make sure to get them in black.

Girl, if you don't have a pair of pointed black heels, you go get you some right now. And do those sweet things justice. If you're awkward walking in heels, look up some YouTube videos on how to do it confidently. Good posture, shoulders back, shoulders relaxed, and walk!

Okay, side note. Is anyone as obsessed with "Barbie: Princess and the Pauper" as much as I am? If so, you'll know what I mean when Julian sings "shoulders back, tummy in, pinky out, and lift the chin". Umm yeah. That little, plastic man knew how to give heel-walking advice. Good Gracious. I just realized how much good advice is in that song he sings. New blog post idea. Be there.

I'm not saying to go splurge on Louboutin, but you can if you want of course. I personally have some amazing black patent pointed stiletto heels that cost less than $30, and they still look new after a few years of wear!

Elegance tip: Make sure the heel isn't too high. 1-3 inches is a great length. Mine are three, but I wouldn't go any higher than that. I'd also be careful with how much of a platform they have! Platform heels are starting to be a thing of the past, and classic heels have a timeless vibe anyway.

7. Leather or Faux Leather Sneakers - White

Note the "leather". Not canvas.

We all need a pair of plain, white, leather sneakers. I say leather because white canvas sneakers will break your heart. End of story. They get dirty after a few wears and are never the same again. I've gone through 4-5 pairs of white canvas sneakers, and even with washing and whitening they didn't last very long.

But, boy, when I got my first pair of faux leather ones! Shoot! Those clean up really nicely every time. I have a special whitening paste I make and apply with an old toothbrush, and those get treated after every few wears. They still look brand new, and I've worn them way more often than my others. (On faux leather sneakers, you can also use a magic eraser on the non-rubber parts. Who knew!)


So in short, basically keep it to blacks, browns, and beiges. Keep it quality over quantity. Remember, we're going into the cold months, so it's almost time to put away the open toed shoes and sandals for a while!

If you liked this post, I've got more coming!

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