How to Pick the Perfect Pair of Shoes for Different Pant Styles

Before you ask yourself “what shoes do I wear with these pants,” read on to learn which styles create the perfect pairing…

By: Niki | October 10, 2017

With fall in full swing, it’s officially ‘pants season,’ and it’s safe to say we’re spoiled when it comes to the many styles of pants out there! It can be so fun to try out new styles, but it also bears the question “what shoes can I wear with these pants?” We’re taking the mystery out of it by creating your go-to guide for which style of shoes pairs best with certain pant styles! Scroll on to see our pairings…

What to wear with… Skinny Jeans

Skinny jeans have seemed to be the go-to for many the past several years, and it’s not only because they’ve become new new “it” pair of pants, they also offer a lot of versatility and a variety of options when it comes to putting together outfits from head to toe.

  1. Booties: best when rolled or cuffed to the top of the bootie. Click here for a guide for effortlessly cuffing and rolling your pants
  2. Tall Boots: slip your skinnies right into your favorite pair of tall or thigh-high boots
  3. Heels: this creates a slender and chic look for a night out
  4. Flats: ideal for comfort, flats style extremely well with any pair of skinny jeans

Product Details: Booties from Tradehome Shoes | Tall Boots from Macy’s | Heels from Macy’s | Flats from Macy’s

What to wear with… Leather Leggings

Leather leggings have pretty much become a fall style staple, so it’s no wonder they can pair so perfectly with many different shoes…

  1. Booties: paired best when the leggings can fit nicely into a lower-ankle bootie
  2. Flats: try mixing textures by opting for a suede or velvet pair of flats
  3. Heels: paired best with pointed-toe pumps, but still works with many kind of heels

Product Details: Booties from Macy’s | Flats from Francsca’s | Heels from Macy’s

What to wear with… Jogger Pants

Joggers have been trending for a while now, so if you’re jumping on the bandwagon, here are a couple pairs of shoes that work well with them!

  1. Sneakers: especially for more of a sweatpant jogger, sneakers and tennis shoes are a great fit for a sporty or athleisure look
  2. Heels: for more of a dressy jogger, heels (both pumps and strappy) are always the way to go

Product Details: Tennis Shoes from Journey’s | Heels from Macy’s

What to wear with… Boyfriend Jeans

With their not-so-fitted style, boyfriend jeans can be harder to style. Luckily, there are a few pairs of shoes that work particularly well depending on the kind of look you’re going for.

  1. Ankle bootes: best when rolled or cuffed to the top of the bootie. Click here for a guide for effortlessly cuffing and rolling your pants
  2. Strappy heels: this look is pulled of well when the ankle strap of the heels hit an inch or so below the hem of the jeans
  3. Sneakers: styled for a more laid-back and casual look

Product Details: Booties from Macys | Heels from Macy’s | Sneakers from Journey’s

What to wear with… Leggings

Leggings have easily become a fashion favorite for their comfortable ways and endless outfit options, but what shoes work best with them?

  1. Flats: flats are a great option for leggings, and can be worn for many occassions
  2. Tennis Shoes: for a sporty look, tennis shoes are a great go-to for leggings
  3. Tall or thigh-high boots: because they cling so well to the leg, leggings are a perfect option for tall or thigh-high boots

Product Details: Flats from Macy’s | Tennis Shoes from Tradehome | Boots from Macy’s

What to wear with… Raw-Hem Jeans

Raw-hem or fringe-hem jeans are newer to the fashion scene, but have grown in popularity for the fall season. We say let your fringe fly! The shoes that work best for this pant style have to do with their ability to show off the raw hem and create a focal point for an outfit.

  1. Short Booties: for booties that don’t come up the ankle too much, raw-hem jeans can work exceptionally well
  2. Mules: this style of shoe is not only trendy for fall, it works perfectly for raw-edge jeans
  3. Pumps: pumps not only add length to the legs (while raw-hems tend to cut the length without them), they work well for when you want to dress up this style of jeans

Product Details: Booties from Macy’s | Mules from Macy’s | Pumps from Macy’s

What to wear with… Wide-Leg Pants

With all the retro vibes taking the spotlight this season, we’re seeing an increase in cropped wide-leg pants. The trickiest task is finding the perfect shoe for this style of pants… Wonder no longer!

  1. Strappy Heels: strappy heels allow your legs to be lengthened, which is really important for a style of pant that can be quick to cut leg in the wrong places
  2. Mules: Sticking with the retro vibes, mules are a great option for wide-leg pants, especially if you are taller and your pants tend to be more of a crop-length

Product Details: Heels from Express | Mules from Francesca’s


Want more style tips? Click here!


I have the privilege of being on the amazing Marketing, PR and Fashion team as the Digital Marketing Manager at West Acres. When I am not managing our social and digital platforms and brainstorming content ideas, I am the woman behind (and sometimes in front of) the camera – creating content and working with the media to create segments to introduce the latest trends! When I’m not at the mall, you can find me watching “Friends,” eating ice cream by the carton, spending time with my family and friends, feeding my Pinterest addiction or crossing off destinations on my traveling bucket list.




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