My Favorite Boots To Wear With Dresses

Fall really kick starts the season for wearing boots with dresses and skirts. As the weather starts to get colder, I find myself wanting to layer my outfits with boots. Not only do boots add warmth, but they also add texture and detail to your outfits. I love how adding a pair of boots can instantly make a dress look more effortless and casual. So today I’m sharing my favorite boots to wear with dresses and skirts.

There are a few boot styles that I aways reach for when styling my dresses for fall and winter. And even in early spring. I basically think about the type of occasion I’m dressing for, whether it’s a big event or a casual lunch. This is my first step in deciding which boots to pull out of my closet.

Next, I think about the weather. I’ll save my suede boots for days when it’s not raining, and there is no snow on the ground. I’ll also opt for a block heel over a skinny heel when the weather is not cooperating. If it’s really cold, I’ll choose knee high boots over ankle boots for extra leg coverage.

Last, I think about the overall style I want to achieve. Slouchy suede boots will give off a more relaxed and casual vibe then sleek leather knee high boots. Ankle boots will also give a more effortless vibe, while shiny leather can look more elevated. Now let’s dive into my favorite boots to wear wit dresses!

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 My Favorite Boots To Wear With Dresses

Slouchy Suede Boots

Suede boots, especially slouch suede, makes a dress appear more relaxed. Not only are these suede boots super warm, but they add so much texture to an outfit. When I want to dress down a dress but still look polished, I’ll choose slouchy suede boots over leather boots.

Choosing a midi or maxi dress with a slit, like this dress, draws the eye down to the boots. Having a little bit of skin showing at the top of the boots keeps the outfit from looking too heavy. You can also achieve this with a shorter dress. I would wear this type of outfit for daytime looks where you want to look casual chic. Like lunch with friends!

Leather Knee High Boots With Dresses

My favorite type of boots to wear are leather knee high boots. They always give a polished and elevated look. You really can’t go wrong with leather knee high boots. I just added these brown boots to my wardrobe recently. Dark brown boots are always so hard to find. I’ve been looking for a good pair the last few fall seasons. They usually come in suede.

I’m very happy I found these brown boots. I actually saw them last year too, but they were sold out by the time I got to them. I’m happy they brought them back. They are so timeless, and will be a go-to for years! I took a size 7 which is my usual size in this brand (I think they run on a little large since I’m generally a size 7 or 7.5).

Brown is the color of the fall season so it’s the best time to get yourself a pair. Shoes are always one of those items I think it is worth investing in. Good shoes will last for so many years. And a classic style like these leather knee high boots will remain timeless.

Ivory Boots

Wearing ivory boots is an easy way to brighten up an outfit. They are a must for wearing with your winter white outfits. I would choose to wear ivory boots with patterned dresses, and dresses with a bit of ivory already in them. This creates a cohesive look.

This midi dress I’m wearing is a great example, since it has a lot of ivory in it. The boots really blend in well. I would also wear ivory boots with this midi dress, and this floral dress. While you can go for an all monochrome look, I like to pair the ivory with some darker colors for fall and winter. It helps to create a seasonal look with some contrast.

These ivory boots are already slouchy so you do not have to slouch them yourself. I love the mid calf height for giving just a hint of skin underneath dresses, but knee-high boots work well too. These fit true to size. I’m wearing a size 7.5. I find them to be very comfortable despite the skinny heel. Here are some more ivory boots from my tried and true brands:

Ankle Boots and Skirts

In additional to wearing boots with dresses, I apply the same theory to wearing them with skirts. For shorter dresses and skirts, I like wearing knee high boots. It gives you more coverage, and a more elevated look. For longer skirts and dresses, ankle boots can be fun! Just showing a little bit of skin above the boot really breaks up the outfit.

Choose leather ankle boots when you want a polished look. For a more laid back vibe, choose suede ankle boots. I love these western inspired boots. They have a pointed toe (that is not constricting), a welted sole, and a block heel. The block heel makes walking super easy. They are also really great shoes to wear with straight leg jeans!

These boots come in a range of sizes from size 33 to 45. That’s really incredible! In addition to that, they also come in narrow, medium, and wide widths. I find these incredibly comfortable, even with the pointed toe. They have 5mm of plush foam padding. I love that! This shoe brand has really thought of it all. Take your true size unless you plan on wearing very thick socks.

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Riding Boots With Dresses

Leather riding boots are the perfect accessory for an equestrian inspired outfit. Bringing in darker tones like burgundy sets the fall mood even more! Choosing riding boots makes your outfit appear more casual. Riding boots are a great idea if you will walking a lot since they usually have a flat or low heel.

My dress is equestrian inspired with the belt print design. It’s a great fall dress to wear to Thanksgiving dinner, fall family photos, or just to elevate your every day look. There is also a navy shirtdress version with the same print if you want more coverage.

In addition to wearing your riding boots with dresses, they also pair extremely well with leggings and a chunky turtleneck sweater. I’m wearing these boots which you can take 15% off your first order with SF-TARA-15. You can read more about the brand in this previous post.

Black boots

You can’t go wrong with classic black boots. Black boots are a versatile wardrobe staple. They can instantly elevate any dress, making them a must-have part of your classic capsule wardrobe.

While there are so many styles of black boots to choose from, I am partial to this pair of mid-calf boots. They leave a little extra room to show off the legs. This is great if you are petite, and knee-high boots usually come up too high for you. This is one of the brands I have a discount for. Use TARAFHM15 for 15% off.

Wearing dresses with boots adds a chic glamour to your looks. Pin this post to Pinterest so that you can refer to it later when you are looking for timeless outfit inspiration.