Style Guide: How to Match Shoes with Outfits

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Shoes have a special place in every woman’s heart (apart from diamonds)! However, things get complicated when it comes to matching them with any outfit. Footwear can make or break your entire style; therefore, choosing them wisely is essential.

Choosing the right footwear to wear with an outfit is an art. We are here to share a comprehensive guide so you can match your shoes with your outfit. Whether you want to match them with something as extravagant as a party gown or something as simple as a solid-colored t-shirt, we’ve got you covered.

Types of Footwear and How to Wear Them

1. Stilettos

While many women prefer wearing stilettos with dresses and maxis, they look good with casual wear. We don’t say it is wrong to wear stilettos with party wear or formals, but we have other types of heels for that. Just pair the stilettos with ripped boyfriend denim and an oversized t-shirt; it will look magical.

MSONLYDN High Heels Women Platform Heels

2. Kitten Heels

Kitten heels are a wardrobe staple if you don’t like wearing sky-high heels. These shoes go with anything, including regular dresses, casual pants, formal pants, shorts, mid-length skirts, and more. During summertime, opt for the open toe or slingback ones to provide comfort to your feet. The best part is, kitten heels won’t provide discomfort to your feet even after wearing them for a long time.

L.K. Bennett Women's Leopard Kitten Heel

3. Slides

Slides are great to pull off that effortless look. You can pair a slide with your daily casual fit and start your day. Moreover, slides are a great footwear option for your summer, spring, or early fall casuals.

YDN Women Ballet Flats

4. Peep Toes

Peep toes are always classy to wear and go well with any dress that exposes your legs till the knees, for example, a mini-skirt. If you want to make your legs look sexier, you can opt for a peep-toe pump with your knee-length dress. There are many varieties of peep-toes. If you are not comfortable wearing the ones with stiletto peep toes, then go for the wedges. Or, you can also wear flat peep toes with your full-length leggings.

Marc Defang Peep Toe Pumps

5. Gladiators

If you are a fashionista, then a pair of gladiators must be present in your shoe closet. Keep them for wearing with your boho dresses and make a style statement. Since gladiators are mostly ankle-length, they will go well with midi dresses or mid-length skirts to keep the footwear star of the show. If you have chunky feet, go for those with thicker straps. Gladiator boots are also there to save you from the muddy puddles of the monsoon. You can wear knee-length gladiator boots with mini skirts.

Women's Sandals

6. Moccasin

Compared to other types of shoes, moccasins are more loosely fitted. So, they are comfortable to wear in summers and springs. It means you can easily pull it off with your mini skirts or frocks. These also go well with boyfriend jeans or formal pants.

Twisted X Women Slip-on Driving Shoes

7. Boots

There was a time when boots were associated with winters only. But now comes a variety of different styles. Choices with boots are limitless, and you can pair them with any type of fashionable women’s clothing. With summer fits or long dresses, you can wear ankle-length boots.

Free People Boot

8. Wedges

Wedges are substitutes for those ladies who are not comfortable wearing heels but still want to wear heels. Wedges are more stable and keep you balanced than stilettos. You can wear wedges with varieties of outfits and make a style statement. They go well with denim, dresses, formals, and many more. Try to wear muted colors like black, blue, or brown with formals.


9. Sneakers

Sneakers are versatile shoes and can save your day if you are confused about picking footwear. For walking, running, traveling, sneakers are comfortable and stylish to wear. However, try to avoid sneakers with a maxi or midi dress as it looks a bit odd.

Golden Goose Slide Sneaker

10. Ballerina

Ballerina flats go with any dress and make it look even more flattering. You can hoard some neutral colors of ballerinas in your shoe closet to contrast them with any casual dress. For formal wear like pants, pencil skirts, and palazzos, you can choose glossy ballerina pumps to pair with.

11. Slip-Ons

Slip-ons were once considered backdated and boring in the world of fashionable shoes. But it is proved wrong, and now slip-ons are stylish, comfortable, and versatile. They are great for casual wear and even go well with dresses. There are multiple colors of slip-on, so you should collect a few. Slip-on is a blended choice of comfort and style for your airport look. In addition, you can wear slip-on during summers as they are open-ended, so air can flow easily through them. You can also wear them with your winter outfits paired with socks.

XYD Women Pointed Toe Flats

12. Chelsea Boots

The best thing is, Chelsea boots are great to wear with both formal and casual dresses. Unlike other boots, these types of boots have a clean look for which they complement various kinds of outfits without looking uncoordinated. Based on the weather, Chelsea boots should be avoided during summers as they can get uncomfortable and hot. Other than that, they get along well in other seasons.

Frye Women's Chelsea Boot

13. Loafer

Loafers are a blessing in the world of shoes. Loafers can adapt themselves to both luxurious and boring outfits. Be it ladies’ blazers, suits, pencil skirts, end your look with a loafer, and you won’t regret it. These are great for cocktail events and make you look dapper. You can wear loafers with your casual fits as well.

Mona Women's Classic Penny Loafer

14. Platform Heels

Platform heels go well with mini skirts, denim, or even party dresses like gowns. These shoes can elevate any of your boring looks. Moreover, platform heels are more comfortable than any other type of heels as they keep the angle of your feet in an upright position.

SCHUTZ Women's Platform Sandal

15. Flip Flops

If you live in a hot and humid climate, flip-flops can be your best friend to wear with any type of casual outfit. Slide on your flip flop for quick grocery shopping, or visit a shopping mall, etc. Flip flops are not meant for formal wear or events.

Tory Burch Women Thong

Color Combinations to Choose with your Outfits

  • Plain Black: a plain black color shoe goes well with any kind of outfit, whether formal or informal. You must have a good pair of black shoes in your shoe closet. Try to have a few variations like sandals, silhouettes, wedges, pumps, etc.
  • Skin Nude: Invest in a pair of classic nude heels. The nude color should be close to your skin tone. Such plain colors pair well with blingy and gorgeous outfits.
  • White Sneakers: a pair of white sneakers is classy and versatile. They match any western outfits of any color and are great to wear regularly.
  • Printed: printed shoes can elevate any boring outfits and work amazingly as a style statement. When you wear printed shoes, it will be an attention-grabber. So, keep your outfit a bit neutral.

Do’s and Don’ts with Shoes

Before you plan to pick the next shoe with your outfit, you have to maintain some cardinal rules. Since footwear is the real deal-breaker, so you need to follow some of your tried and tested do’s and don’ts with footwear.


  • Although we have mentioned a bunch of shoes that go with various kinds of outfits, time and place matter. Do keep in mind why you are wearing the outfit. Of course, you can’t choose to wear blinky shoes or high-heels if you are going to the office.
  • Know the season when you are picking shoes. If it’s the wet monsoon season, go for boots. There are many kinds of boots that go well with various types of dresses, such as bondage boots, gladiator boots, wellington boots, cowboy boots, etc.
  • Always pick the right shoe size to prevent unwanted discomfort.
  • Contrast shoes with your dresses. For example, if you are wearing a black dress, you can pick red heels.
  • Go for nude colors with glittery, sparkly, or sequined dresses.
  • Always prefer comfort over style.


  • Say no to sneakers with maxi or gowns
  • Don’t wear sparkly shoes with sequined dresses
  • Don’t completely match your shoes with your dress. It is quite old-fashioned
  • Avoid wearing white shoes during monsoon
  • Avoid eye-catchy colors or printed shoes for formal occasions

Final Thought

I bet you also secretly dream of owning an entire room of shoe closet like the Kardashian/Jenner sisters. But let’s be honest, you don’t need that many. Work with whatever you have currently to bring the best in you. We hope our guide was insightful enough to ‘guide’ you through picking the right shoes with every outfit. At the end of the day, always pick comfort over style!

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