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I’ve Tried Them All & These are the Best Shoe and Dress Pant Pairings for Women (By Pant Style)

I’ve Tried Them All & These are the Best Shoe and Dress Pant Pairings for Women (By Pant Style)

Making sure you wear the best shoes with your pants can be tricky, considering how many styles of dress pants exist for women!

To confuse matters further, many different pant lengths and widths are trending right now!

To look stylish and put-together, I've compiled a style guide on how to wear your dress pants with the right shoes. With both heeled and flat options, I'll give you pointers on hemlines and general outfit advice.

If we haven't met yet, hi! I'm Cristina, ShoeTease's digital stylist. With over 20 years of experience in the industry, designing shoes and styling outfits for women just like you.

Collage of different styles of black dress pants with the best shoes to pair them with.

Related: Ankle Boots to Wear with Dress Pants, Shoes for Cropped Pants, Shoes to Wear with Wide Leg Pants

Shoes to Wear with Dress Pants – By Pant Style

1. Straight Leg Dress Pants

Collage of black long straight leg dress pants with 4 shoes to wear them with.

Starting off our shoe and dress pant styling post with full length straight leg pants. These are not only the most common type of dress pants for women, but they are the easiest to style with many types of shoes.

Now there are many types of straight leg pants. But the ones we're focusing on here are a mid width leg, which have far more room than slim pants and less than wider leg pants.

  • Sneakers: Classic white sneakers are great, but you can also choose platforms, high tops or retro styles. Chunky designs can also work, but only with wider straight-leg jeans, as these can overwhelm your outfit.
  •  Loafers: From slim to chunkier styles, loafers are perfect shoes for dress pants. I love black loafers with black pants, but you can experiment with off-white or even tan styles.
  •  Ballerina Flats: a great look with straight leg dress pants that hit right at the base of the ankles or foot. Very long pants that topple over your flats aren't practical. Try a trendy square toe, Mary Jane or classic style.
  •  Slides: Almost all slides look great with straight leg dress pants that end right above or at the ground. You can choose a kitten heel slide, a flat leather slide, or even one with some platform if the pants accommodate them.
  •  Heels: I love a longer pant with tall heels, where the pant leg hits the between the top or bottom 3rd of the heel. If your pants are ankle length, than a kitten heel on any shoe style can work.
  •  Ankle Boots: For cooler weather, a classic pointed or square-toe ankle boot with a 2-3 inch heel looks fab. You can also have fun with western styles or combat or Chelsea boots that have a bit of a heel or platform.

2. Shoes with Wide Leg Dress Pants

Collage of black wide leg dress pants with 4 shoes to wear them with.

There are so many great shoes to wear with trousers that have a wider fit all through the leg.

When giving advice on wearing dress pants, there are two kinds of stylists: those who recommend wearing a slimmer shoe with wide-leg pants and those who don't. 

I fall somewhat into the latter camp, as there is a time and place for both!

A full-length wide-leg pant easily accommodates a chunkier shoe, balancing the outfit and keeping your pants from dragging on the ground.

That said ankle length wide leg dress pants can look great with a finer pump or heel, as long as at least 1/3 of the heel is visible.

Sneakers: I love platform sneakers with long, loose, wide-leg pants, as they complement the look and avoid dragging the hem on the ground. Chunky sneakers work great, too, for sportier looks. Wide-leg pants falling at the ankle? Try a classic sneaker!

  • Loafers: Chunky or platform loafers are trendy and great paired with wide leg dress pants. As with sneakers, if your pants aren't so long, you can to for a classic pair too.
  • Platforms: As you've figured, all platform shoes look great with longer, wide pants! I love a 70s-style sandal for dressier outfits.
  • Clogs: An unexpected pairing with wide leg pants for laid-back looks. I love the wooden heels popping out as I walk!
  • Ankle Boots: All kinds of ankle boots look fab with wide-leg pants, but I particularly like the lightly squared toe with a 2.5-inch block heel as it balances the proportions of the trousers.

Check out all my wide leg dress pants outfits in my post speciically about wearing shoes & boots with wide leg pants!

ShoeTease Facebook Group block reading: don't know what to wear join our free facebook group for styling and outfit help beside an image of a woman organizing her shoes and another woman standing in a fashionable outfit with jeans.

3. Shoes with Slim or Skinny Dress Pants

Collage of black slim leg dress pants with 4 shoes to wear them with.

Slim pants are still a staple for many women, especially in a more corporate environment. Shoes should be refined and sleek to align with slenderness of the pants–especially if you have larger feet. No one's going to look like a clown on my watch!

Have a smaller foot size proportionately to your legs? Then you can get away with platforms, and even chunkier shoes, as they'll not be as prominent. I have a size 8.5 foot and I can't get away with slim pant and larger shoes!

  • Slim-line Sneakers: These sneakers will look sleek with your slim trousers. I love a good white sneaker, but try a black or striped pair like Adidas Samba or Puma Palermo if you have particularly long feet.
  • Classic Loafers: A Gucci Horsebit-style loafer is a classy pairing, but any single-sole loafer will do! Love black on black.
  • Single-Sole Slides: Low leather slides look lovely with tighter pants for warmer weather and won't overwhelm your outfit.
  • Kitten Heels: choose a kitten heel sandal or slide with skinny pants for a chic pairing.
  • Sleek Ankle Boots: A tight fitting ankle boot with slim pants is key. I love a matching boot color to elongate the leg. Trending boot and pant styling is all about a taller, tight shaft so the ankle boot fits over or underneath the pant hem with no ankle gap. In terms of boot shape, a mid to low kitten heel boot with a pointed toe works great, but a tapered squared-toe boot with a block heel can also work.

4. Shoes with Full-Length Flare Dress Pants

Collage of black long flare dress pants with 4 shoes to wear them with.

Flared dress pants are incredibly flattering and come in many fits. Most flared styles fit slimly through the leg and widen from the knees down. Others are more roomy in the thighs, making the flare less prominent.

The wider the base of the flared pant, the more a substantial shoe like platforms and chunky styles pair well. The longer the flare trouser, the higher and chunkier the heel should be, making the legs appear long and lean.

  • Platform Sneakers: Platform sneakers are best with long flares, which really elongate the legs. A classic white sneaker can never fail if the flares aren't overly long.
  • Heeled Loafers: Great for a casual or business look. Try trending chunkier loafers, too!
  • Platform Shoes: Wear a taller, chunkier platform with wider/longer flared pants. For shorter full-length and less flared and styles, choose a slimmer platform. Wedge heels are a great option for flared pants in the spring.
  • Block Heels: Block heels are perfect for long flared trousers. Try a sandal, bootie or pump.
  • Pumps: Speaking of pumps, a sleek pointed toe or squared toe pump will complete a flared pantsuit or elevated evening look!
  • Heeled Ankle Boots: Classic ankle boots with a block heel, pointed or tapered squared toe look great with flares with fall to spring outfits.

5. Shoes with Cropped Dress Pants

Collage of black slim cropped dress pants with 4 shoes to wear them with.

Slimmer cropped pants are dainty, and the shoe choices should reflect that. Think single-sole options, pointed pumps and kitten heels.

The pant hem usually falls right above the ankle bone, so you can show an ornate heel, shoe motif or strap around the heel or ankle.

  • Classic Sneakers: Keep these slimline and simple not to overwhelm the pants.
  • Classic Loafers: Chic and versatile, this combo will look great with business casual outfits. With this trouser styling, you can have some fun with socks and loafers!
  • Simple Slides are easy shoes to pair with slimmer cropped pants. For height, you can even rock a kitten heel or low block heel.
  • Kitten Heels: A great way to elevate your cropped trousers for work or a night out on any style of shoe like a sandal, pump or bootie.
  • Slingback Pumps: These are my favorite shoes to wear with dress pants. They are slimmer and are the perfect opportunity to show off a slingback strap!
  • Tall Ankle Boots: A tall shaft ankle boot is a must, preferably with a slim low to medium heel and a tapered toe. A visible gap between the top of the boot and pant hem will look dated.

A note for petites: I recommend styling high-waisted cropped dress pants with a medium heel to elongate the legs.

Looking for more cropped pant styling advice? Check out my dedicated post on pairing your shoes with cropped pants and capris, which includes full outfit advice, too!

6. Kick Flare or Wider-Bottom Cropped Pants

Collage of cropped black flare dress pants with 4 shoes to wear them with.

Cropped dress pants that are flared (aka kick flares) or wider at the base can go with so many shoe and heel styles. 

The wider hem allows for even chunkier shoes, while the shorter fit complements even the daintiest shoe!

  • Retro Sneakers: All sneakers (albeit not very chunky) will look great. However, my style choice is a retro sneaker: a good cross between a slim and chunky shoe, like these New Balance ones.
  • Slides: minimal leather slides or even puffy and athletic slides can work. The sportier versions obviously for more casual looks.
  • Block-Heel Sandals: The flares on these cropped trousers balance out a block heel. I prefer a 2.5-3 inch block heel on a slide or strappy sandal.
  • Kitten Heels: Low-heeled stilettos, block pumps, and sandals look great with cropped flares or wider cropped pant styles. They are great for showing off straps at the ankle or heel.
  • Tall Ankle Boots: A tall shaft ankle boot hiding under the hem is a great look for cropped slim dress pants. A block heel with a square toe will give a retro vibe, while a sock boot with a stiletto heel and pointed toe will look chic and elegant. You can even wear a calf boot with this pant style.

Now that you know what shoes to pair with different dress pant styles:

As you've learned, there are many different shoes to wear with dress pants and women's trousers. Footwear with dress pants is very dependent on the pant style.

Larger, wider pants can accommodate chunkier shoes, while slimmer pants tend to pair best with sleek shoe and heel styles.

In the end, it really depends on the style of outfit you are looking to create and your personal preferences! I hope this post has given you some guidelines to style your dress pant outfits, which you can always choose not to follow.

My number one styling rule is that the shoe and pant pairing you choose should make you feel great in your clothes and in your skin!

Confidence is the gateway to your most stylish self!

Need styling help? Join my FREE FaceBook Group, where I share style tips and tricks and members post photos and questions for fashion feedback or fun!

ShoeTease Facebook Group block reading: don't know what to wear join our free facebook group for styling and outfit help beside an image of a woman organizing her shoes and another woman standing in a fashionable outfit with jeans.

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