I wish I had a dollar for every time I have been asked “What shoes should I wear with this?” It never fails, we find the perfect outfit to wear and we get so excited! Then we start to think about what shoes will complete the outfit!

I hear this all the time from clients. I can’t possibly cover the right shoe for every outfit in one blog post, so I’m going to start with trousers and jeans.

As with all of my styling advice, the first question I ask is where will you be wearing this? It’s important to think about the setting when considering my suggestions below. Once you know where you’re going, you can decide on the level of dress and heel height.

Then we pick the shoes!

For Cropped Skinny/Tapered Leg Pants…

I would suggest any of the following shoes for this style. Be sure to wear your cropped pants right at, or just above, the ankle.

The cropped skinny pant is one of my personal favorites because it is so versatile. If your crop pant is denim or a more casual fabric, sneakers, ballet flats or even “loafers” are great options. You can also choose a wedge, ankle boot (closed or open toe) or heel if you want the height. If you choose a boot or wedge, I would stay with a simple style so you don’t disrupt any look that would elongate. I would steer away from ankle straps for the same reason. Be sure, when wearing a boot, that your pants and boots don’t touch. When your pant bunches up against the top of the shoe it draws your eye right to that point instead of elongating.

Here are some suggestions for the cropped ankle pant/jean.

Suggestions for the Crop Ankle Pant. Everything here works well with denim and casual pants. For a dressier look opt for the suede mule, snakeskin or leather options. — **Suggestions for the Crop Ankle Pant.** Everything here works well with denim and casual pants. For a dressier look opt for the suede mule, snakeskin or leather options.

For Full Length Skinny/Tapered Pants…

If your skinny pant is full length, shy away from the flats and definitely no sneakers. I would also suggest a simple heel. It doesn’t have to be high. If you opt for a boot, try something that hugs the ankle like the one below.

Suggestions for Full Length Skinny Pant… If you must do a flat keep it very simple! Again, ankle hugging boot to elongate the leg. — **Suggestions for Full Length Skinny Pant…** If you must do a flat keep it very simple! Again, ankle hugging boot to elongate the leg.

For Crop Boot Cut…

A simple sneaker with this crop boot cut works, just remember to keep the colors similar.

Make sure the flare is just above the ankle bone. If it’s too short you will look like you have “cankles” and if it’s too long it won’t look right with any shoe. I recently had a flare crop jean that didn’t work with any shoe because it was too long. I finally had it hemmed and I was able to wear it with quite a few shoes in my closet!

I often choose a more simple shoe for this look. Choose a ballet flat or a basic sneaker. A wedge, mule or block heel could also work. If you opt for a shoe that has more detail along the vamp, try to keep the colors similar between shoe and pant. (See photo at top of post)

Notice how the tip of the boot is the only part of the shoe that shows!

For Full Length Boot Cut…

No flats here. This cut needs a heel, even if it’s just an inch. I always keep my boot or flare pants a little longer so that I have more shoe options. I made the mistake of cutting one of my favorite jeans too short and now I can only wear them with a 1” cowboy boot. When choosing a heel height you want the pant to skim the top of your shoe like in the picture to the right.

For Wide Leg/Palazzo Pants…

For a more casual wide leg you can try a platform sandal or sneaker.

I would always choose something with height! If it’s a super casual pant like the “sweatpants” to the right, then a platform can keep the look casual but still give you height. It doesn’t have to be super high but should give you a lift to compensate for the flowy fabric.

Any of the shoes shown above for Full Length Boot Cut would work for Wide Leg Palazzo Pants too!

For Boyfriend Jeans…

With my favorite boyfriend jeans and one of my boyfriends ;)

I love Boyfriend jeans because they are also pretty versatile! I prefer to always wear my boyfriend jeans rolled. At some point I’ll offer a video on my “rolling techniques”! Pair these with all sorts of fun sneakers, ballet flats, heels, wedges and ankle boots. Remember to roll enough so the jeans and boots don’t touch!

I know this is a lot of information so I’d love to offer a Free Consult. Sign up to receive my weekly emails and I will contact you to make some suggestions for a pair of pants that have you stumped. I will work with what you have in your wardrobe. If we can’t find something there I will make some suggestions! If you’re only interested in the links to some or all of the shoes in this blog I can send you those too! Even if you’re on the email list sign in below. I’ll make sure you don’t double up!

Fashionably yours,