Choosing shoes to go with your dresses can be trickier than selecting the best shoes to go with your pants. That’s because if you get it wrong, you risk looking frumpy or making your legs look shorter or your ankles look wider. While there are no hard and fast rules, there are shoe choices that will be more flattering with your dresses. That’s why we’re looking at shoes to wear with dresses in this article.
What to Consider when choosing shoes to wear with dresses
Before we get into some specific shoes to wear with certain styles of dresses, let’s think about what to consider when making your selection.
How formal is your dress?
If you’re heading to a formal event and you’ve chosen a formal dress, your shoes should be at that same level of dressiness.
Jas @thefashionstylefile above chooses ankle strap sandals with her button-down dress. Of course, you don’t have to choose heels, but if you are opting for a formal look, make sure your flats are also dressy. There’s inspiration in this article on low heel party shoes.
Recreate her outfit with this similar dress, sandals, clutch and earrings.
hem-length
Think about how your shoes work in balance with your hem length and how much leg you are showing off. For example, if you’re wearing a short dress, you may want to play down the ‘sexiness’ of that by opting for ballet flats or pointed loafers. A knee-length dress looks great with heels; a midi will go with anything, and a maxi dress can look good with heels or flats, depending on how formal it is.
Jess @elegantlydressedandstylish above (read her style interview here) shows how a pair of wedge-heeled sandals are a good choice for a more casual maxi dress.
Get her look with this similar maxi dress (another option here), sandals, clutch, belt, scarf, earrings and sunglasses.
how full is your skirt?
If you’re wearing a dress with a full skirt, you could balance that fullness with chunkier shoes like sneakers or wedges.
Emms @beautifuleveryday_uk above shows how to wear your sneakers with your tiered dress. Or, if you are choosing a more retro style of full skirt, then heeled or flat pumps would work well. Pumps also look good with slimmer pencil skirts.
Steal her look with this similar dress (another option here), sneakers, shoulder bag and earrings.
which part of your legs do you like best?
The shoes you choose to wear with your dress can help to draw attention to the part of your legs you like best. An ankle strap, for example, will draw attention to your ankles.
Claudia @glamupyourlifestyle above (read her style interview here) wears strappy tan sandals.
Recreate her outfit with this similar dress (another option here), sandals and necklace.
Activities and Climate
It goes without saying that the majority of your outfits will need to combine both style and practicality. Consider the weather and whether you will be walking for any length of time.
Eugenia @theeageofgrace above (read her style interview here) opts for knee-high boots that will keep her legs warm while looking stylish.
Check out this similar sweater dress, puffer vest (another option here), boots, tights, bag, earrings and sunglasses.
Shoes to wear with dresses
Let’s start with some shoe choices. Then, we’ll show you which of those shoe styles will go best with each type of dress.
Below, you can see a good choice of shoes from flats to heels, rounded to pointed toes, ankle straps, wedges, peep toes and menswear-inspired styles. Plus, of course, you don’t have to stick to shoes, booties and boots will also work well with lots of your dresses.
BERNARDO FOOTWEAR Faryn Pointed Toe Pump – Sam Edelman Tarra Pump – Sam Edelman Tahira Pump – BERNARDO FOOTWEAR Square Toe Ballet Flat
Nine West Pruce Ankle Strap Sandal – Franco Sarto Korie Sandal – Fly London Yuba Wedge Sandal – Aerosoles Pastel Wedge Sandal
Paul Green Cayanne Peep Toe Sandal – SARTO by Franco Sarto Calista Kiltie Loafer – U-lite Perforated Oxford Shoes – Naturalizer Morrison Sneaker
Sam Edelman Usha Pointed Toe Bootie – Sam Edelman Laguna Waterproof Lug Sole Chelsea Boot – LifeStride Gracie Knee High Boot – Naturalizer Jessie Knee High Riding Boot
SHOES TO GO WITH DRESSES
We’re concentrating on dress styles here, but the same guidelines apply to skirt shapes. Below, you will find the main dress styles, along with some shoe options that will look good with them.
wrap dress
Wrap dresses are so versatile. They flatter all figures, they can be dressed up or down, and most shoes will look great with them. Because the wrap dress is a classic style, classic shoes such as heeled pumps, slingbacks, and ankle strap sandals will work well. However, you could also add an edge to your wrap dress with peep-toe booties or wear with knee-high boots.
Maggy London Abstract Print Wrap Front Midi Dress – BERNARDO FOOTWEAR Faryn Pointed Toe Pump – Nine West Pruce Ankle Strap Sandal – Sam Edelman Tarra Pump – Paul Green Cayanne Peep Toe Sandal
asymmetric
If you’ve been following 40+ Style for any time, you’ll know we’re big fans of asymmetry. Because an asymmetrical hemline gives your look an edgy style, choose an edgy pair of shoes to go with it. Look out for chunky heels, cage styles, and shoe boots. Or, choose to mix styles and add a more formal style to your asymmetrical dress. Wear heeled ankle strap sandals and a clutch bag for a night out.
COS Asymmetric Gathered Satin Midi Dress – Nine West Pruce Ankle Strap Sandal – Franco Sarto Korie Sandal – Fly London Yuba Wedge Sandal – Paul Green Cayanne Peep Toe Sandal
shirtdress
Another great, versatile choice is the shirt dress. Since a shirt dress tends to be more casual, it goes incredibly well with more casual shoe choices such as flats, wedges, and sneakers. But, again, you can always mix casual and formal in any outfit, so you can also choose pumps and a tote bag to dress up.
Caslon Utility Tie Waist Shirtdress – Sam Edelman Tarra Pump – Aerosoles Pastel Wedge Sandal – U-lite Perforated Oxford Shoes – Naturalizer Morrison Sneaker
midi dress
Midi dresses go with so many shoe styles, making them a great addition to your closet as you can dress them up or down for any occasion by simply switching your shoes and bag. If your midi dress has edgy elements like the zip on the COS dress (below), it will work well with edgier shoe choices like chunky sandals. Wear it with wedges for your vacation, with pumps for dinner, or sneakers for casual days. Midi dresses also look good worn over knee-high boots or with ankle booties.
COS Flared Zip-Up Midi Dress – BERNARDO FOOTWEAR Faryn Pointed Toe Pump – Fly London Yuba Wedge Sandal – Aerosoles Pastel Wedge Sandal – Naturalizer Morrison Sneaker
maxi dress
Unless you are wearing a very formal style of maxi dress, perhaps because you’re at a wedding or event that calls for a formal dress, then you can really wear your maxi dress with anything from heels to sneakers. To dress up your maxi dress, wear it with block heels or heeled booties. If your dress is more on the casual side, you could wear with your flat sandals or sneakers.
Karen Millen Abstract Print Pleated Wide Sleeve Maxi Dress – Sam Edelman Tarra Pump – Nine West Pruce Ankle Strap Sandal – Franco Sarto Korie Sandal – Sam Edelman Usha Pointed Toe Bootie
pencil dress
A pencil dress is a particularly great choice to flatter hourglass curves or to create the illusion of curves if you have a more athletic figure. Since a pencil dress has a certain old-fashioned, retro appeal, your shoe choices work best if they are also on the classic side. Look for heeled pumps, slingbacks, Mary Jane styles, and ballet flats.
GRACE KARIN Pencil Dress – BERNARDO FOOTWEAR Faryn Pointed Toe Pump – Sam Edelman Tarra Pump – Sam Edelman Tahira Pump – BERNARDO FOOTWEAR Square Toe Ballet Flat
A-line dress
An A-line dress works for all ages and figures. It is particularly good for pear shapes because the a-line style of the skirt skims over the thighs and hips. Because an a-line style has a certain ’roundness’ to it, it works well with round-toe styles. But there are no hard and fast rules in fashion. You can also add a contrast to your outfit by wearing with menswear-inspired chunky loafers or with pointed heels or flats.
Nordstrom Zip Front Sleeveless Ponte A-Line Dress – Sam Edelman Tarra Pump – Sam Edelman Tahira Pump – BERNARDO FOOTWEAR Square Toe Ballet Flat – SARTO by Franco Sarto Calista Kiltie Loafer
t-shirt dress
Another casual style is the t-shirt dress , This style from COS (below) should come to just above or on the knee, depending on your height of course. Choose casual shoe styles like chunky-sole sandals, sneakers, lug-sole boots, and knee-high boots. Or team casual and dressy by wearing over-the-knee boots.
COS Oversized-Fit Wool T-Shirt Dress – Fly London Yuba Wedge Sandal – Naturalizer Morrison Sneaker – Sam Edelman Laguna Waterproof Lug Sole Chelsea Boot – Naturalizer Jessie Knee High Riding Boot
shift dress
A shift dress has a 1960s feel to it in shape, so it works well with other retro shoe styles like ballet flats and Mary Janes. You can also team with heeled pumps, sandals, and a clutch bag for an evening out.
Eliza J Bow Shoulder Shift Dress – BERNARDO FOOTWEAR Faryn Pointed Toe Pump – Sam Edelman Tahira Pump – BERNARDO FOOTWEAR Square Toe Ballet Flat – Nine West Pruce Ankle Strap Sandal
shoes to wear with dresses: a halterneck
The halterneck dress is a great choice for inverted triangle body shapes as it helps to balance out wider shoulders. Wear it with a huge choice of shoes, from block heels or wedges for a more casual feel to pointed flats or pumps for a dressier look.
COS Pleated Halterneck Dress – Nine West Pruce Ankle Strap Sandal – Franco Sarto Korie Sandal – Aerosoles Pastel Wedge Sandal – Sam Edelman Usha Pointed Toe Bootie
sweater dress
Just as the t-shirt dress is a casual style for warmer months, the sweater dress can be the perfect choice for colder weather. Opt for chunkier, casual styles of shoes that will complement the dress, such as brogues, loafers, lug sole booties or knee-high boots. Team with opaque tights for winter and Fall.
ZOE AND CLAIRE High Neck Tie Belt Sweater Dress – SARTO by Franco Sarto Calista Kiltie Loafer – U-lite Perforated Oxford Shoes – Sam Edelman Laguna Waterproof Lug Sole Chelsea Boot – LifeStride Gracie Knee High Boot
cocktail dress
A cocktail dress is a dressy option for a party, an event, or dinner. You can choose formal shoes to go with it. Pumps, heeled sandals, and Mary Janes will work well for your heels. Or look for ballet flats or pointed flats for a lower, more comfortable party choice.
Eliza J Mock Neck Lace Sheath Dress – BERNARDO FOOTWEAR Faryn Pointed Toe Pump – Sam Edelman Tahira Pump – BERNARDO FOOTWEAR Square Toe Ballet Flat – Nine West Pruce Ankle Strap Sandal
sundress
A summer sundress pairs well with casual sandal styles. Choose flat sandals, block heels, or wedges. You can also opt for sneakers and a denim jacket for a casual look. To dress up your sundress for the evening on vacation, wear it with heeled sandals and a clutch bag.
Treasure & Bond Apron Sundress – Franco Sarto Korie Sandal – Fly London Yuba Wedge Sandal – Aerosoles Pastel Wedge Sandal – Naturalizer Morrison Sneaker
shop the shoes to wear with dresses below:
What are your favorite combinations when it comes to shoes to wear with dresses? Tell us in the comments below.
Continue reading:
- The Best Dresses To Hide Your Tummy
- What Shoes To Wear With Different Styles Of Pants
- The Most Flattering Dresses For Women Over 40, 50, 60 Or Any Age
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Feature image by Jas @thefashionstylefile
Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.
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