How to Dress Casually

Co-authored by Ashley Kahn and Amy Bobinger

Last Updated: December 12, 2020 References

Casual dress makes up the majority of what most people wear, but looking good while dressing down takes a little more effort than just tossing on some sweatpants and a baggy T-shirt. Luckily, showing off your style in comfortable, practical clothing is easy and fun!

Part 1

Part 1 of 3:

Choosing Casual Basics

1
Avoid clothes that are too tight. You don't have to wear clothes that are super-baggy, but tight-fitting clothes can make you look uncomfortable, defeating the purpose of casual wear.
- Form-fitting dresses or tight pants are more suitable for a night at the club than a casual day spent relaxing.
- Clothes which are highly structured, such as garments with stiff collars or strong shoulders, usually come across as dressy.
2
Slip on your favorite comfy jeans. Weekends and downtime are the perfect time to wear your favorite pair of jeans, and you can pair them with just about anything to create the perfect casual look.^{[1]
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Ashley Kahn
Wardrobe Stylist
Expert Interview. 25 September 2020.}^{[2]
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- Wear baggy jeans with a fitted T-shirt or tank top for a look that's relaxed and cool.
- Pair slim-fitting jeans with a relaxed collared shirt and canvas sneakers for a casual look that's still appropriate to wear anywhere.
- You'll be ready for whatever comes your way when you wear a pair of boots under flared or bootcut jeans.
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3
Wear a pair of shorts if the weather is warm. Keep cool on a hot day with a pair of shorts in your favorite style! Opt for shorts with a relaxed fit in a soft fabric like cotton, nylon, or broken-in denim.^{[3]
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- A silky tank top, sandals, and shorts that hit a few inches above the knee are the perfect feminine look for a summer day outside.
- Cargo shorts, a graphic tee, and flip flops will have you giving off surfer vibes wherever you go!
4
Wear a T-shirt for the ultimate casual look.^{[4]
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Expert Source

Ashley Kahn
Wardrobe Stylist
Expert Interview. 25 September 2020.} A super-soft T-shirt is the ultimate in comfort. As a bonus, T-shirts are endlessly versatile, so you can show off your personal style.^{[5]
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- Wear a T-shirt embellished with gems or studs to show your glam-but-casual side.
- A T-shirt with an ironic or witty saying shows your sense of humor on your off days.
- Choose a plain white T-shirt for a look that's timelessly casual.
5
Opt for an untucked polo or button-down if you need to run errands. Just because you're off-duty doesn't mean you have nothing to do. If you want to look presentable without sacrificing your casual style, wear a nice shirt but leave it untucked.^{[6]
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- A polo shirt and cargo shorts is appropriate for a casual lunch date.
- Wear an untucked button-down shirt with the sleeves rolled up, a pair of straight-leg jeans, and loafers to look preppy yet casual.
6
Wear a long sweater and leggings to look perfect on a cool weekend. Leggings are stretchy and warm, and while they may not be work-appropriate, it's okay to live in them any time you're not in the office. Wear your leggings with a pair of low sneakers or boots, depending on your style.^{[7]
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- You can wear a long tunic with leggings for an ultra-casual look any time of year.
7
Wear a dress and sandals for a summery, feminine look. A flowy dress made of cotton, jersey, or other lightweight material is the perfect balance between casual and pretty. Be the cool girl wherever you go in a sundress, sandals, sunglasses, and bright lipstick.
- Make a spaghetti-strap dress even more casual by wearing a T-shirt underneath it.
8
Wear a chunky sweater with jeans to show off your preppy-casual style. A cable-knit sweater with a pair of dark jeans and loafers will have you looking like you're on holiday from an Ivy League school!^{[8]
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Part 2

Part 2 of 3:

Adding Casual Outerwear

1
Top your outfit with a hoodie for the ultimate casual outerwear. A cozy hoodie will make you feel right at home no matter where you are, whether you're binge-watching Netflix with a friend or heading to the grocery store.^{[9]
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2
Wear a flannel over your T-shirt for a grungy look. Channel your inner 90s rockstar by tossing on a plaid flannel over a band tee. This is best done on a cool day, but if you're committed to the casual grungy look, you can rock it anytime.^{[10]
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3
Choose a military-style jacket for a look that's versatile and rugged. Military jackets add a neutral layer to any outfit. These are usually either khaki or olive green, and they're made from a lightweight, water-resistant material that's perfect for almost any season.^{[11]
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- Complement your jacket with non-matching neutrals like black and white.
- Make your look pop by wearing a bright color under your military jacket.
4
Opt for a leather jacket to give off a rocker vibe. Think James Dean, the ultimate in casual cool, when you're styling your leather jacket — keep the rest of your look relatively clean to let the jacket stand out.^{[12]
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- Wear your jacket with simple T-shirts or tanks, or get tough with a rocker tee and black skinny jeans.
- If you don't wear animal products, imitation leather is perfectly okay!
5
Layer on a cardigan for a conservative casual look. Cardigans are perfect to wear over a dress, a button-down shirt, or a T-shirt, and their cozy style will have you wanting to curl up with a good book all through the afternoon.^{[13]
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Part 3

Part 3 of 3:

Wearing Casual Accessories

1
Slip on a pair of sneakers to make any outfit more casual. Make the most of your downtime with a comfortable pair of sneakers. Whether your favorite sneakers are high-tops, cross-trainers, or skater shoes, wear them with almost anything to show off your casual style.^{[14]
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- Wear canvas sneakers with a pair of slim-fitting jeans rolled up at the ankles for a look that's chic yet relaxed.
- Wear a pair of sneakers when you have to wear a suit to show everyone you're still casual even when you're dressed up.
2
Go for sandals when the weather is warm. Sandals are all about comfort, so let your feet breathe whether you're on the beach or running errands downtown.^{[15]
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- Show off a colorful pair of slide-on sandals with a pair of cropped jeans.
- Make any outfit tough yet girly with a pair of gladiator sandals.
3
Be ready for anything by pairing jeans with boots. Whether you're staying in the city or working on a ranch, a rugged pair of boots say you're not above getting a little muddy.^{[16]
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- A plain white tee, relaxed jeans, and cowboy boots are an All-American look that works on anyone.
- Skinny jeans and lace-up ankle boots are the perfect way to balance casual toughness with street style.
4
Wear a baseball cap for a no-fuss look. A baseball cap is quintessentially casual, especially when it's perfectly broken in. Wear it with jeans and a t-shirt, or opt for a tank top to show off sun-kissed shoulders in the summer.^{[17]
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- If you have long hair, wear it in a loose side braid or a ponytail.
5
Accessorize your jeans with a canvas belt. Whether you need to hold up your pants or you just like the look of a belt, a belt made from canvas or a braided material is the perfect casual touch. Avoid leather belts, as they can look too dressy.^{[18]
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- Tie a scarf around your waist for a pretty belt alternative.
6
Wear a pair of sunglasses if you'll be outside. Sunglasses are casual and cool, not to mention they protect your eyes from harmful UV rays. From oversized rhinestoned glasses to a sleek pair of aviators, you can find sunglasses to fit any style.