What Shoes Go With What?

Flat Shoes

Not matter what season, women everywhere are constantly wondering, what shoes should I wear with this outfit? Whether you’re dressing up for an office presentation, in a wedding, or just trying to impress the man of your dreams, this blog is perfect for you, because we’re going to break down the various types of shoes, and what looks good with them! Simple & easy and you can refer back to it at any time!

Let’s dive in!



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Wedges are very comfortable and fashionable. They can go with nearly every outfit.

They vary in height, material, and texture just in the heel.

Wedges add definition and shape to heavy ankles, making them appear thinner.

It goes with casual dresses, trousers, and knee length dresses.

Wedges can look a little clunky, especially when paired with very tight-fitting clothing.

Kitten heel

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Kitten heels have a shorter thinner heel usually, and so they are easier to wear for a longer period of time.

This is practical alternative to the pump works with both office attire and eveningwear, and the shorter heel makes them super-comfortable.

Kitten heels also look great with uber-feminine retro looks a la Audrey Hepburn.

They are completely workable and very trendy.


The Stiletto

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Stilettos — the ultimate in sexy — make your legs look amazing. Wear these shoes with pencil skirts or slim pants.

Stilettos are the most hunted of high heels when it comes to prescribed events. It works much better with long and voluminous full length dresses.

You can also wear them with palazzo pants or a nice full skirt.

Skinny heels are slimming, but can look disproportional on thicker legs; choose a more substantial heel to balance everything out.



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This Roman inspired footwear is best paired with a long tunic dress or maxi-style halter dress.

Most gladiator sandals are versatile, and look good with either plain or trendy dresses, mini or maxi.

Ballet Flats

Flat Shoes

Ballet flats are a classic that never goes out of style, ballet flats lend a trendy yet ladylike touch to an outfit.

You can wear them with almost anything, and depending on the style of the flat, it will either help dress it up, or tone it down!



No shoe closet is complete without a great pair of knee-high boots, and no fashionista is complete without a good pair of thigh-high boots.

Pair with leggings to extend the boot, nice pair of denim jeans, better yet right before it gets too cold pair it with some shorts and moto jacket.

Also, equestrian boots look great over skinny jeans. Booties with a heel make a run-of-the-mill knee-length skirt into a fashion statement.

Even cowboy booties get new life when paired with a cute sundress and cowboy boots with jeans.

Final Thoughts…

What you wear on your feet can totally transform the rest of your look. The right shoe can elongate and slim your legs, dress your gown up or down, make you flirty or business-like, and basically make or break your entire look.

I know it sounds complicated, but that’s why we are here! If you’re stuck on a pair of shoes to go with your outfit, let us know! We can help! Leave us a comment below with your favorite shoe choices!

14 thoughts on “What Shoes Go With What?”

  1. Ballet flats are an all time favorite and during the winter of course the boots. Great selection of what to wear and when.

  2. I love wedges more than any other height lifting shoe because they’re actually comfortable to wear. I hadn’t paired my gladiators with dresses before for some reason. Thanks for the idea!

  3. Such an awesome guide! I always wear flats or sneakers when I have a busy day of running errands and shopping. But when it’s time to dress up, I love putting on some heels or boots.

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