The Quintessential

The tall heeled boot is a classic must have for any Fall/Winter season. Characterized by pointy toes and stiletto heels, this boot goes well with pretty much everything.

Celebrity Sightings

Nicole Richie’s boots fit the bill. They hit right below the knee, are plain black leather, have pointy toes and stiletto heels. Notice she’s wearing with skinnies and a full top.

How to Wear

As I said before, you can wear this boot with pretty much anything. First, find a boot that’s comfortable for you. Make sure the calf is not too tight, but not too loose either. Also, make sure the heel is at a comfortable height for you.
With Skinny Jeans and Full Top: Take some inspiration from Nicole Richie and wear your boots with Skinny Jeans and a Full Top. If you don’t have Skinny Jeans, try a Straight Leg Jean. That will work just as well. You shouldn’t have to fold or pleat your jeans to fit them into the boot. This makes a huge lump and unwanted bagginess at the top of your boot. Your jeans should fit right in. Pair with a full top to contrast the streamlined silhouette. If you want something a little more tight fitting, try a T-Shirt style tunic and a long cardigan.
With a Dress and Tights: Wear these feminine boots with a dress and tights to dress things up a bit. Try a contrasting color or pattern for the tights to draw attention to your boots and avoid looking like it’s all one piece. Definitely opt for a full or flowy skirt. Wearing a pencil skirt or bandage dress with this style can easily make you look like a hooker.

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The Quintessential

This is definitely my favorite boot style this season. The Over the Knee boot is characterized as being tall enough to go over your knee. Some have fold down flaps that allow you to wear the boot as an Over the Knee boot or a Knee-High boot. This boot is not quite as versatile as the Classic Heeled Boot, but it is a lot more fun.

Celebrity Sightings

Kate Moss is the queen of Over the Knee Boots. She must own like 20 different pair! The biggest thing I notice about her style is that she always wears the boots the same way: with Skinnies.

How to Wear

If we learn from the pro, we know that pretty much the only way to wear these boots and not get propositioned on a street corner is to wear them with Skinny Jeans. So, what about tops?
Layer, layer, layer! You can wear a tight fitting T-shirt or fitted button up, but wear another, longer layer over that. A blazer, a cardigan, a sweater, etc.

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The Quintessential

The Riding Boot is a new trend for this season. Sure, the style’s been around for awhile, but it’s never been quite so popular as it is this season. And, it’s being worn with pretty much anything. Riding boots are flat, have wider leg openings and often have buckles or tabs to make them look a bit more rustic.

Celebrity Sightings

If you’re walking long distances or trying to stay warm in the city, riding boots are your best bet. Kirsten Dunst pairs her boots with Skinny Jeans and warm layers on top.

How to Wear

Riding Boots can be worn with a variety of outfits. Dress them up or down, depending on your mood.
With Skinny Jeans: Follow Kirsten’s example and pair your boots with Skinnies and lots of layers on top. You can also go for a tighter top and accessorize with a long scarf.
With a Girly Dress: Pairing Riding Boots with a feminine dress may seem like a contradiction, but it’s actually a nice look. It makes your dress seem more casual and wearable for everyday.

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