How to Select Shoes to Wear with an Outfit

Co-authored by Ashley Kahn

Last Updated: March 18, 2023

Some women get a bad rap for having shoe obsessions. With all of the endless styles and colors of footwear, to choose from, who can blame a woman for having her closet stacked from top to bottom with shoes? This guide will teach you how to select shoes to wear with an outfit no matter what the color of the outfit, the occasion or season it is. Get started at step one below.

Method 1

Method 1 of 8:

Consider the Color

1
Choose shoe colors that match your clothes instead of colors that compete with your clothes.
- Wear simple black heels or flats when wearing a dress with a bright, bold pattern. If you were to wear a more complex shoe, it would be too overwhelming in the opinion of some. Obviously, you can wear whatever shoes you like provided there is no dress code to obey or health and safety issues to consider.
- Consider neutral or 'nude' heels or flats if you have on a sparkly evening top.
2
Add zest to a plain outfit by wearing brighter shoes.
- Add a pop of color by pairing a red heel with a black or brown dress.
- Try a dressy shoe with a funky pattern, like alligator skin, if you have on a simple blouse and neutral trousers or jeans.
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3
Home in on a color found in your clothing if you’re wearing a multi-colored outfit. For instance, if you have on a blouse with a geometric pattern including the colors purple and pink, consider a deep purple shoe.
4
Avoid strict color matching. Do not wear one solid color from head to toe. If you have on a blue blouse and a blue skirt, avoid wearing blue shoes, unless you want to. Remember the fashion police can't actually charge you with anything!
5
Consider different shades. If you have a light pink blouse on, try wearing a rose-colored flat or heel instead of a shoe in the same shade of pink.
6
Select standard colors for professional settings.
- Wear brown or black leather shoes at a conservative office. Grey and navy a red good choices for the office too.
- Incorporate color only if you have a less strict office with a corporate casual dress code.

Method 2

Method 2 of 8:

Choose the Right Shoes for the Season

1
Be flexible in the spring. You can choose both winter shoes and summer shoes as your wardrobe evolves through the spring.
2
Lighten up in summer. Summer is the time to enjoy your sandals and espadrilles. Just be sure to enjoy them without socks.
3
Pull back in the fall. You can still be somewhat flexible as your wardrobe transitions to winter, but avoid the sandals and espadrilles. They don't match with the heavier fabrics and colors of autumn.
4
Choose practical shoes for winter. Choose loafers, flats and boots. Make sure that your heels are wider to avoid slippage.

Method 3

Method 3 of 8:

Selecting Heels

1
Pair stiletto heels with clothing that already helps elongate your leg, such as pencil skirts and slim pants.^{[1]
X
Expert Source

Ashley Kahn
Wardrobe Stylist
Expert Interview. 25 September 2020.} The stiletto creates the illusion of further length, making your legs look even more slender and attractive.
2
Choose low heels, like kitten heels, for a more versatile option. Kitten heels look appropriate for the office while still looking feminine enough for a night out.
3
Avoid heels with ankle straps or T-straps if you have short legs. Straps also have a tendency to cut off the leg, making it look short.
4
Avoid heels that are more than four inches tall if you have short legs. Ultra high heels make the calf muscle flex more, which leaves your leg looking less slender.
5
Wear oval-shaped or square-toed heels if you have large feet. Avoid tapered or pointy heels that may end up making your feet look even larger.
6
Avoid wearing extremely high heels or sexy, strappy designs in professional settings, depending on your profession..... A low to moderately high heel is fine, but keep things conservative. A closed-toe, low-heeled pump works best.
7
Wear heels for formal and semi-formal events. Go with closed-toe or open-toe pumps for banquets and other formal events. Opt for closed-toe, open-toe, or strappy heels for semi-formal occasions like cocktail parties.
8
Try wearing your heels with casual clothes to add a touch of style to your everyday wear. Throw on a pair of stilettos with your jeans and fitted t-shirt to give the outfit an automatic style boost.

Method 4

Method 4 of 8:

Selecting Sandals

1
Select a pair of low-heeled sandals for a versatile, feminine look. Wear low-heeled sandals with virtually any skirt length or pant length.
2
Consider a pair of strappy, high-heeled sandals the next time you wear your little black dress or similar evening wear. Higher heeled sandals make your legs look especially long, thanks to both the heel height and the extra skin showing on the top of your foot.
3
Save flip-flops for short-term casual settings. Limit them to the beach or, if necessary, for running errands.
4
Wear walking sandals with casual outfits. Shorts, capri pants, and some dress-down sundresses work with walking sandals, but avoid wearing them with dressier clothes.
5
Use heeled-sandals to make casual clothes look a little nicer. For instance, try matching a pair of kitten-heel sandals with a casual denim skirt and fitted blouse to make the outfit a little dressier.

Method 5

Method 5 of 8:

Selecting Flats

1
Wear flats with knee-length or above-the-knee skirts, capri pants or Bermuda shorts.
- Avoid flats with long skirts. In many cases, though not all, flats worn with maxi-skirts can make a woman look dowdy.
- If you do wear ballet flats with mid- to maxi-skirts, consider a less-than-flat ballet flat with a slightly elevated heel.
2
Select a pair of decorative flats to dress an outfit up. Select a pair of less decorative flats for casual occasions.
3
Also avoid flats with skinny pants unless you have narrow hips. Otherwise, you risk making your legs look disproportionate.
4
Avoid casual flats at the office or in other professional settings. You may choose a formal style, such as a simple flat made of black or brown leather.
5
Consider flats for some semi-formal occasions. For example, try matching a decorative pair of flats with a nice sundress for a garden party or other outdoor dress-up occasion.

Method 6

Method 6 of 8:

Selecting Boots

1
Save your boots for autumn and winter. Boots evoke images of colder weather and prevent airflow from reaching your foot, making them warmer.
2
Wear a pair of short, skinny-heeled boots with a boot-cut or straight-legged trouser or dark-wash jean. The heel of this boot makes it sexy and helps it to elongate your leg, while the boot style makes it appropriate for heavy fabrics.
3
Consider a pair of wide-heeled fashion boots when you want to look stylish but are afraid of slipping on icy sidewalks. While they do not elongate your leg quite as well skinny-heeled boots, they do dress up an outfit.
4
Select a pair of fashion boots that does not cut off your leg at its thickest point. Knee-high boots work well because many women's legs are narrowest directly below the knee. Knee-high fashion boots also make an excellent choice for skirts and dresses.
5
Wear snow boots for snow and rain boots for rain. Switch to your fashionable boots when you're comfortably inside.

Method 7

Method 7 of 8:

Selecting Oxfords and Loafers

1
Consider a pair of oxfords or loafers for the office. As a conservative style, loafers are appropriate for nearly any professional setting. They can go brilliantly with trousers as well as with dresses and skirts.
2
Select a pair of low-heeled loafers to wear with knee-length pencil or A-line skirt.
3
Wear either flat or low-heeled oxfords with trousers.

Method 8

Method 8 of 8:

Selecting Sneakers and Athletic Shoes

1
Wear athletic shoes designed for your sport. If you are a runner, for instance, wear running shoes with supportive insoles.
2
Match athletic shoes with athletic clothes. If you have workout clothes on, wear workout shoes.
3
Stick with low-key sneakers for non-athletic clothes. Avoid running shoes or other obviously athletic shoes for everyday wear.
4
Wear pseudo-athletic shoes that slip on with an open back for daily errands or for work in the garden.

Community Q&A

Question

What color should I wear with a white blouse and grey pants?

Community Answer

If you want to give it a funky look, opt for a vibrant color like red or magenta. If you want to give it a formal look, go for brown or purple or maroon. Heels always give a dressy look to an outfit, but heels should also suit your personality, enhance the overall look, and make you feel comfortable.
Question

I have very colorful shoes - what do I match to them?

Community Answer

Colorful shoes will usually go well with neutral colors like black, white, and gray. If you're wearing a more colorful outfit, you can also match shoes to one of the colors in the outfit, or to your accessories (necklace, purse, etc.).
Question

Can I wear sneakers with a fitted short gown?

Community Answer

It depends on the occasion. If it's relatively casual, sure. If it's formal, no.

Warnings

Extremely high-heeled shoes and flip-flops have both been known to cause foot damage when worn excessively. Limit these shoes to their proper settings—formal and evening for high heels, and short-term casual for flip-flops—to avoid causing permanent damage to your foot.

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