How to Wear a Dress to School

Last Updated: September 6, 2019

If you're someone who enjoys putting together cute outfits for school, you may be getting tired of the classic pants and a top combo. Although wearing a dress can be a super cute and easy way to spice things up, many people have a lot of trepidation about wearing a dress in a casual situation for the first time.

Part 1

Part 1 of 3:

Choosing the Right Dress

1
Choose your stores wisely. The key to wearing a dress to school or college is to make sure you don't look like you're walking around ready for prom. Stay away from expensive formal stores, and instead look where you would normally shop for jeans and T-shirts. This is an easy way to find casual, comfy dresses for day to day wear.
- Look online in stores you'd never expect. No matter what a store specializes in, they probably have at least one casual dress.
2
Pay attention to details. Certain details can really ensure that your dress is appropriate for day to day wear. Remember that you'll be wearing this to school, so make sure that it fits your dress code comfortably.
- Length - Shorter dresses are typically thought of as more casual. Although you can make certain longer dresses work, you would usually want to look for a dress that's mid thigh or past your knees. However, keep in mind the activities you'll be doing at school that a short dress may get in the way of, as well as dress code and wardrobe malfunction issues. A dress at least as long as your knees is a safer bet.
- Pattern - Stay away from glitz and sparkle. Despite this looking a little fancier, this kind of glamour is a little loud for school. A plain colored dress, or one with a smaller floral pattern is a great place to start.
- Fabric - Stiffer, more structured dresses can look very formal. Plus, they're pretty uncomfortable to sit in, and you'll be doing a lot of that at school. Opt for a more light and flowy fabric, especially for the skirt.
- Neckline - Avoid high and deep v necklines if you can. A more casual neckline like you would see on a T-shirt gives you a more relaxed feel, as well as being more classroom appropriate.
- Ruching in the back. Some casual dresses feature some non decorative ruching in the back panel of the dress. This is made out of an elastic material and is there to help the dress stretch to fit your body. This is a detail that generally only casual dresses have.
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3
Choose a suitable style. Some specific styles are sure to be a hit.
- Wrap dresses - wrap dresses feature a wrap around the front that usually forms a v neck. Often they have a self tie around the waist or a hidden snap button or stitch to help keep the wrap panels together. Usually this style comes with super pretty short sleeves in a very light cotton fabric. This is an especially great style for school, because the sleeves lend it a comfy schoolgirl look.
- Spaghetti strap dresses - dresses with very thin straps are a super cute choice. The extra detail of a straight or square neckline that often accompanies this style is very unique. Keep in mind the dress code for this one. If your school doesn't allow it, you could try layering something under or over it, as described in the how to style portion.
- Button down dresses - the height of casual cute! These dresses have a long row of non functional buttons going in a line from the neck to the hem. These come in a variety of different styles so you're sure to find one you like.
- Short sleeve dresses - you can't go wrong with one of these. They come in so many different variations and are good for days when you want to be a little bit more conservative and cozy. They also cover the shoulders for those who have a stricter dress code.
- Overall dresses- Simply a pair of overalls with a skirt instead of pants at the bottom. A great transition if you're worried about wearing a dress to school. Usually worn with a T-shirt underneath, so you have lots of styling options. Because of the denim, this is a super cute and classic school outfit.
- T shirt dresses - another great way to make the change from not wearing dresses. Super comfortable as well as cute and offer a lot of styling options as well. Great for a day when you want to feel as comfy as possible.
4
Decide if the dress is appropriate enough for school. If you ever aren't sure if a dress is appropriate enough, decide on two things: can you wear it with sneakers or a denim jacket? and would it be weird if you wore it to a fancy wedding? The answer to both questions should be yes. Also think about how comfortable you'll be in the dress, and how easy it will be to sit, stand, walk, and run in, as well as how it fits into the dress code of your school. If you've checked all these boxes, you're good to go!

Part 2

Part 2 of 3:

Styling Dresses for School

1
Wear the right shoes. Sure, some dresses look great on their own, and some days you just want to throw on one thing and be ready to go. But styling a dress as part of an outfit can be super fun, and it will make you look very put together. It's also a great opportunity to make dresses that don't fit the school dress code more appropriate. Whether you want to go all out or not, you have to wear shoes. Shoes are the most important part of making a dress look casual.
- Try some white sneakers. Sneakers and dress are a classic combo that everyone looks cute in. Go the extra step and wear colored sneaks that match part of your dress.
- Flats and sandals are great too, but remember that you're stepping into slightly fancier territory. Sandals with a heel too high are impractical for school, as you'll be doing a lot of walking and standing.
- Boots are great for the fall and winter.
2
Wear a jacket. Wearing a dress is no reason to freeze to death, and even if it isn't cold outside, jackets can actually elevate your outfit.
- Full length jackets are super cozy and cute, and are most people's first choice, but if you don't want to be too overwhelmed by fabric, go for a cropped jacket that sits at your waist. This is also a very flattering combo.
- Denim or corduroy jackets go well with dresses. Denim looks especially good with pink, yellow, red, and black dresses.
- If it's your style, a men's blazer or jacket can look very nice with a dress.
3
Be careful with the jewelry! Jewelry is a fun way to accessorize, but when worn with a dress, it can easily make things too dressed up. For school, try picking only one accessory at a time. Try dangly earrings one day, a cute pendant necklace on another, and/or a bracelet set on a different day. Do not have all three on at once.
- Match the color of your jewelry with the color of your clothes. For example, dark purple, emerald green, rosy pink, and cream are some of the colors that go well with gold, whereas pastel colors and blue undertones go better with silver.
4
Add a belt. If you feel like your dress is too shapeless, or needs an extra something, try a skinny belt around the waist. This is especially good for giving T-shirt dresses a more defined silhouette. For a pop of interest, match the color of the belt buckle to a necklace or other piece of jewelry you're wearing.
5
Wear a T-shirt underneath. Dresses with straps look really cute over a T-shirt. This is an old trend that has recently made a huge comeback and it looks so nice. This is also an easy way to turn strappy dresses into more school appropriate outfits.
- Start out with a white shirt and layer a dress over it. Make sure the top is tight enough that it doesn't bunch up underneath the dress.
- As you get more used to the idea, go outside of the box. For example, try a dark band tee underneath a denim overall dress.

Part 3

Part 3 of 3:

Making Sure You're Comfortable

1
Get comfortable with it. This might not matter much to you, but for some people this is a huge step out of their comfort zone, and that's fine! Doing things that make you a little uncomfortable help you grow as a person. But it really doesn't have to be too traumatic.
- If you're nervous, practice by wearing skirts and shorts to school. Once you're comfortable with that, try wearing a T-shirt dress or an overall dress first. These are good transition dresses that help ease you into things.
- Don't wear a dress for the first time ever on a very stressful day. The first day of school or the day you have a very stressful science presentation is not a good time to start. All you'll be able to think about is how self conscious you are in your dress, and it will make everything worse. Instead, pick a low stress day when you're already used to school. If your school has short days, try it then, and it will take a lot of stress out of it.
- Remember that you can always wear tights or leggings under the dress if it will make it easier, and you can wear a comforting jacket on top.
2
Take precautions. Have a pair of spandex or similar shorts that you can wear under your dress, and always wear them. You never know what could happen, and it will give you some peace of mind. If there is any other risk of a wardrobe malfunction, try to fix it, or wear a different dress. It always helps to feel more secure.
3
Be confident. Even if you're worried out of your mind, fake it till you make it. You'll be sure to get some compliments in no time!