How to Wear a Dress

Co-authored by Susan Kim

Last Updated: December 28, 2022 References

Dresses are great, simple outfit choices, and there are many ways that you can wear them. Choose a dress in a style and length that works for the occasion, such as a shirt dress for casual days or a maxi dress for more formal events. Add coats and jackets to transform the dress into a dynamic outfit, and finish off the look by adding accessories such as jewelry, scarves, and belts.^{[1]
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Expert Source

Susan Kim
Professional Stylist
Expert Interview. 30 April 2019.}

Method 1

Method 1 of 3:

Choosing Dress Styles and Lengths

1
Pick out a shirt or wrap dress for a versatile option. Shirt and wrap dresses are perfect for day-to-day life, such as for running errands, lunches out, or working around the house. They come in tons of different colors and fabrics, and they’re comfortable and stylish.^{[2]
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- Keep a little black wrap dress on-hand for almost any occasion—you can dress it up with jewelry and heels, or you can dress it down with a jean jacket and sneakers.
2
Wear a maxi dress for leg coverage. A light, colorful maxi dress is perfect for warm weather—you can even choose one with slits down the side for better breathability. During chillier months, wear a jacket over a maxi dress in more muted tones for a nice autumn look.
- Wear a jean jacket over a gray maxi dress in early autumn.
- Put on a spaghetti strap floral maxi dress on a warm summer day.
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3
Select a summer dress made of lightweight materials. In hot weather, you’ll want your dress to be able to breathe. Choose fabrics that won’t trap heat and are lightweight, such as cotton, silk, polyester, and rayon.^{[3]
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- When it's hot, stay away from fabrics that stick to your skin, such as spandex, as these won’t allow air flow as easily.
- Short summer dresses look great with sneakers, flip flops, or wedges.
4
Put on a form-fitting dress to show off your figure. If you’re going out or just want to show off your curves, select a dress made of spandex or a similar material. You can also look for dresses that only hug a certain part of your body, such as your waist, and flow over the rest of your body.
- Wear a chunky leather jacket over a form-fitting dress to create a more dynamic look.
- Select a dress that hugs your chest and waist with a skirt that flows out to accentuate your features.
5
Layer clothing underneath a sleeveless dress to wear in chilly weather.^{[4]
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Expert Source

Susan Kim
Professional Stylist
Expert Interview. 30 April 2019.} If you don’t have any long-sleeve dresses and want to wear a spaghetti strap or sleeveless dress in colder weather, throw on a T-shirt or turtleneck underneath the dress. You can also put on tights or leggings to protect your legs, making your outfit winter-ready.^{[5]
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- Put on a cream turtleneck under a corduroy overall dress for a fall look.
- Wear black tights or leggings under a red dress with black boots for a warmer outfit.
6
Add clothing over the top of a dress to turn it into a new outfit. You can alter your outfit by adding skirts over a form-fitting dress, turning the dress into a top, or add a T-shirt over the dress for a casual look. Flare skirts look especially nice over fitted dresses, as do maxi skirts.^{[6]
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- If you put a T-shirt on over the dress, you can use a belt to create a cinched waistline or use an elastic to tie the shirt to one side.
- If you don’t have an elastic and the shirt is long, try knotting it to create a shorter top.

Method 2

Method 2 of 3:

Selecting Outerwear

1
Create a more casual look by wearing an oversized button-down. An oversized shirt, made of a fabric like cotton or flannel, can make an outfit look less-dressy when worn over it. If you’d like to wear a dress that’s a bit fancier than the occasion calls for, wear an oversized long-sleeve shirt overtop.^{[7]
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- Long-sleeve button-down flannels are a popular option to wear with dresses.
- Wrap the button-down or flannel around your waist if you get too warm, keeping your outfit casual.
- A pair of boots or sneakers would look great with this outfit.
2
Wear a sweater over a dress to turn it into a skirt. This works well with dresses that have a waistline, but you can also create a waistline using a belt. Throw a warm, over-the-head sweater over a dress for colder months, or wear a button-up sweater with a few of the bottom buttons undone.^{[8]
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- Wear a dress with a collar under a long-sleeve button-up sweater, pulling the collar over the sweater for a put-together look.
3
Wear a leather jacket over a dress for an edgier look. Leather jackets, no matter the color, do a great job of toning down a super feminine dress. Pick out a leather jacket that could go with lots of your dresses or tops, and wear it on your next night out.^{[9]
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- Wear a black leather jacket over a frilly red or blue dress.
- Put on a light gray leather jacket over a black knit dress.
4
Choose a denim jacket to wear over a dress for a go-to outfit. Denim jackets are warm, comfortable, and come in many different styles, making them a great jacket choice. Pick out a denim jacket in a certain wash or color, or find a unique jacket with embellishments.^{[10]
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- Wear a denim jacket with roses embroidered on it over a black dress.
- Wear a black denim jacket over a green or purple dress.
5
Select a long sweater with your dress for a cute fall look. Comfy cardigans, whether they’re oversized, long, or more form-fitting, look great with many different dress styles. If you’re wearing a form-fitting dress, consider balancing it out with a more flowy sweater, while a cotton cardigan looks great with dresses with more form-fitting tops.^{[11]
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- Wear a patterned or striped shirt dress with an oversized, soft sweater.
- Put a white short-sleeve sweater on over a summer dress.
6
Make your outfit office-ready by adding a blazer. Blazers instantly make your outfit look more professional, especially if they’re well-tailored. Match a blazer to a dress you’d like to wear to work, to a meeting, or just to create a more put-together look.
- Leave the blazer open to show off the front of your dress, or button a few buttons for an even more professional look.
- Wrap dresses, A-line dresses, and dresses with a straighter skirt look great with blazers.

Method 3

Method 3 of 3:

Adding Shoes and Accessories

1
Wear belts to cinch your waistline.^{[12]
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Expert Source

Susan Kim
Professional Stylist
Expert Interview. 30 April 2019.} Belts turn shapeless dresses into more form-fitting outfits by showing off your waist. Hook the belt over your dress to show off your curves, or simply to add an embellishment to your outfit.^{[13]
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- Wear a chunky brown belt over a denim, shapeless dress.
- Pair a thin, black belt with a dress that has a form-fitting upper half and flowy skirt to accessorize.
- If you’d like to shorten your dress, cinch a belt around your waist and roll extra fabric in the dress over the belt to hide it.
2
Put on a scarf to add a pop of color. During colder months, scarves are a great way to keep yourself warm while also accessorizing. Pick out scarves of varying thickness, patterns, and colors to go with any outfit. You can also opt to tie small, thin scarves around your neck during warmer months, adding a tiny pop of color while eliminating the need for a necklace.^{[14]
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3
Choose jewelry that complements your dress. Match the neckline of your dress with a necklace in an appropriate length, or put on a pair of earrings that complement your outfit’s colors. Jewelry is a great way to add a bit of flair to your outfit, often making your dress even dressier.^{[15]
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- Wear a black choker with a halter dress or a dress with a high neckline.
- Accessorize with gold bangle bracelets or hoop earrings.
- Pair a longer necklace with a dress that has a deep V-neck.
4
Pick out heels or wedges to dress up your outfit. Heels will make any dress look dressier, and they come in so many different styles, colors, and fabrics. Wedges are more of a spring and summer trend, but they tend to be a bit more comfortable than some heels. Wear a dress with heels or wedges to work, out with friends, or to an event.
- Pair a flowy summer dress with white wedges.
- Put on a pair of black heels to go with a blazer and dress.
5
Add sneakers to your outfit for a sportier look. Sneakers can be a great way to make a dress look more casual. If you’re running errands, meeting up with friends, or exploring the city, pair your dress with a comfy pair of sneakers.
- Put on a pair of white Converse with a striped shirt dress.
- Wear Keds (canvas shoes) or a similar style of shoes with a maxi dress.
6
Show off a pair of tall boots or booties with your dress. This combination is a great options for the fall and winter months. Invest in a pair of neutral-colored boots to go with any outfit, such as brown or black. Wear tall boots with dresses of shorter lengths, or wear booties with dresses of varying lengths.^{[16]
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- If you’d rather wear the boots for comfort, put on a pair of booties underneath a maxi dress.

Expert Q&A
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Question

What are some flattering dress styles for a plus-size body type?

Susan Kim
Professional Stylist
Susan Kim is the owner of Sum+Style Co., a Seattle-based personal styling company focused on innovative and approachable fashion. She has over 5 years of experience in the fashion industry, and received her AA from the Fashion Institute of Design & Merchandising.

Susan Kim

Professional Stylist

Expert Answer

Support wikiHow by unlocking this expert answer.

Dresses with an empire waistline are a good choice. Dresses with sweetheart necklines and deep v-cuts are good for plus-sizes as well, as they accentuate the bust.
Question

I am a man. Is it ok if I wear dresses? If not, why?

Community Answer

Yes, you can wear a dress. First, just don't care what anyone thinks. Second, men all over the world wear dress-style clothing in a range of styles. Third, many people wouldn't care less if you wore a dress. And if they do, they're not worth being bothered by. Gravitate to those who like you for who you are, not what you wear.
Question

How do I find the confidence to wear a skirt to school if I’m a boy? I get bullied sometimes but I really want to wear matching skirts with my friend. Any thoughts?

Nico

Top Answerer

Try to disregard what anybody thinks about you wearing a skirt. The key to your situation is to boost your self-esteem. Give yourself compliments everyday, use positive affirmations, and don't criticize yourself. Ignore what others think about you. If other students bully you for wearing a skirt take a deep breath and walk away, or tell a teacher.