How to Look Good and Feel Comfortable In Casual Wear (2024)

By Closet Coach / In Closet Coaching, Fashion Tips, Get Inspiration, What to Wear / On 12 Aug 2022

Clothing designed for casual occasions is called casual wear. In general, it is more comfortable and less formal than other types of clothing. Denim, t-shirts, and sneakers are some of the most common casual wear items.

It is important to keep the occasion in mind when choosing casual wear. For example, jeans and a t-shirt are typically appropriate for casual events, but not for formal ones. For instance, sneakers are perfect for running errands or going to the gym, but not for a night out.


While dressing casually, it is also important not to look too casual. You can achieve this by wearing clothes that fit well and look good on you. A casual outfit can also be dressed up with accessories. Wearing a nice watch or scarf can add polish to an outfit without making it too formal.

It is important to distinguish between casual and formal occasions before we move forward. Casual occasions could include running errands or meeting friends for coffee. For formal occasions, you would dress to impress for events such as weddings, work functions, or other formal events.

Let’s move on now that we’ve established the difference between casual and formal occasions.

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What You Need To Know About Dressing Casually

It’s important to strike a balance between looking too casual and looking chic when wearing casual clothing. Don’t overdress for your casual get-together, but don’t wear sloppy clothes either.

Here are some tips:

  • You should choose clothing that fits well and looks good on you.
  • Dress up your outfit with accessories. A nice bracelet or a light jacket can add polish without making the outfit too formal.
  • Wearing too many trends at once is not a good idea. Your outfit should look like you put effort into it, not like you just left a fashion show.
  • Don’t stray from classic styles. It’s hard to go wrong with jeans, t-shirts, and sneakers.
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The TGIF Look

This is a classic casual look that never goes out of style. The Thank God It’s Friday Look is a universal casual look that can be worn on any day of the week.

These tips will help you achieve this look, depending on your personal style:

  • Wear comfortable clothing that allows you to move freely.
  • Keep it simple. It’s important not to appear forced.
  • Choose items you have worn before and feel confident wearing. A little goes a long way.

For the TGIF look, maximum comfort is key. It’s important to be able to relax and enjoy your clothes, without worrying about them. Plus, you can go from work to play without changing.

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A common TGIF look for men would be khaki pants or dark jeans, a button-down shirt tucked in, and loafers. A denim skirt or black jeans, a white tee or blouse, and sneakers are usually the go-to outfits for women. The style of each individual will differ, but these are some general guidelines.

Casual Date Night Outfit

A casual date night is a great way to spend time with your significant other. It’s relaxing, comfortable, and fun.

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But what do you wear?

Your choice of clothing will depend on your activities. Restaurants vs. bars, indoor vs. outdoor activities, etc. Here are a few general tips:

  1. Start with a basic foundation. It is best to wear a simple top and bottom. Accessories can always be added later.
  2. Choose fabrics that are soft and breathable. You want to be comfortable all night, avoid anything synthetic and too constricting.
  3. Consider darker colors. They tend to be more flattering and slimming.
  4. Personalize it a bit. Your style and personality should be reflected in the items you choose.


It is most important that your shoes are clean and comfortable. You don’t have to be untidy to be casual. Sneakers, loafers, or sandals will work well.

Choose The Right Casual Wear For You

Casual wear is a great way to express your personal style and feel comfortable at the same time. There are many different types of casual wear, but it’s important to choose pieces that fit your personality and lifestyle.

For example, if you’re a busy person who likes to stay active, you may want to choose casual clothes that are comfortable and easy to move in. If you’re more of a laid-back person, you may want to choose clothes that are more relaxed and casual.

It’s also important to consider the occasion for which you’ll be wearing casual wear. For example, jeans and a t-shirt are perfect for a casual day out, but they wouldn’t be appropriate for a more formal event.

The best way to choose the right casual wear for you is to experiment with different styles and see what looks best on you. Don’t be afraid to try something new – you may be surprised at how great you look in casual clothes.

The I Care But Don’t Care Look

Planning ahead is the key to ‘The I Care But Don’t Care Look’. It’s the ‘I woke up like this’ look, but we all know it’s not entirely accurate.

With this look, a little effort goes a long way. It’s important to appear as though you didn’t try too hard, even though you did. Choose simple clothing items that can be easily thrown on, and avoid anything that looks too polished.

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Some key clothing items for this look include:

  • A pair of well-fitting jeans
  • Polo shirts or t-shirts
  • A cardigan or light jacket
  • Sneakers or flats

It’s also a good idea to coordinate colors, but not to match them too closely. With light wash jeans and white sneakers, you could wear a navy blue cardigan.

Keep a catalog of your outfit ideas so that you can easily recreate them when you’re in a pinch. Having planned your outfit ahead of time will make it appear as though you didn’t even have to think about it.

The Benefits Of Casual Wear

Wearing casual clothes has several benefits. The first advantage of casual clothing is its comfort. Even at home, you can feel relaxed and comfortable.

The second benefit is that it’s usually cheaper than other types of clothing. As a result, you can save money over more formal options.

Casual wear can sometimes be more stylish than other types of clothing. Choosing well-made and fashionable casual clothes will help you achieve this goal. A simple black dress can be more stylish than a formal gown, and a pair of jeans can be more stylish than a skirt.

It is also perfect for everyday activities to wear casual clothing. Wear it to the grocery store, to the bank, or even to work. After a long week at work or on the weekend, it’s a great way to feel relaxed.

The best thing about casual wear is how versatile and easy it is to wear. Different pieces can be mixed and matched to create many different outfits.

The versatility of casual wear makes it a popular choice for many people. Online shopping is the best place to find casual wear. Online retailers offer a wide selection of clothing options. You can find everything from jeans and t-shirts to dresses and skirts.


Size Wise™️ Closet Coach, an online marketplace and personal style coaching service. We offer services to help women and men feel more confident about their personal style choices. Our services include a personal style consultation, online shopping, and closet assessment.

Next, visit your local stores. Casual clothing is available in many stores, but it’s important to try it on before you buy it. By doing so, you can make sure it fits well and is comfortable.

Last but not least, don’t forget thrift stores and consignment shops. You can often find designer brands for a fraction of the price at these stores.

There is a casual wear store for every style and budget.

Don’t Guess Casual Wear

Dressing casually doesn’t have to be a guessing game. Following a few simple guidelines can help you look polished and put together without sacrificing comfort.

Hopefully, this article has helped you figure out your desired look and given you some ideas on how to wear casual clothes that make you feel confident and stylish. Feel free to contact us if you have any questions. Our consultants are happy to help.

And remember, when in doubt, Shop Size Wise™️.

As a seasoned fashion enthusiast with a keen eye for style and a depth of knowledge in the world of casual wear, I've not only kept up with the latest trends but also delved into the principles that underpin the choices we make in our everyday wardrobe. My expertise is rooted in a combination of personal experience and a commitment to staying abreast of the dynamic fashion landscape.

Now, let's dissect the key concepts discussed in the provided article on casual wear:

1. Casual Wear Defined:

  • Clothing designed for casual occasions is known as casual wear.
  • It's characterized by comfort and informality, contrasting with more formal attire.
  • Common items include denim, t-shirts, and sneakers.

2. Occasion-Appropriate Dressing:

  • Emphasizes the importance of considering the occasion when choosing casual wear.
  • Differentiates between casual and formal events.

3. Balancing Casual and Chic:

  • Advises on achieving a balance between looking too casual and maintaining a chic appearance.
  • Stresses the significance of well-fitted clothing and the addition of accessories for a polished look.

4. TGIF Look:

  • Describes the timeless "Thank God It's Friday" casual look.
  • Highlights the need for comfort, simplicity, and confidence in the choice of clothing.
  • Offers specific outfit ideas for both men and women.

5. Casual Date Night Outfit:

  • Recommends starting with a basic foundation and personalizing the outfit based on the planned activities.
  • Suggests softer and breathable fabrics, darker colors for a flattering effect, and clean, comfortable shoes.

6. Personal Style and Comfort:

  • Advocates choosing casual wear that aligns with personal style and lifestyle.
  • Encourages experimentation with different styles to find the best fit.
  • Acknowledges the role of comfort in selecting casual clothing.

7. The "I Care But Don’t Care" Look:

  • Discusses the concept of appearing effortlessly put together with minimal effort.
  • Recommends simple clothing items like well-fitting jeans, polo shirts, and sneakers.
  • Emphasizes coordination of colors without an overly polished look.

8. Benefits of Casual Wear:

  • Highlights the comfort and affordability of casual clothing.
  • Suggests that casual wear can be stylish, versatile, and suitable for various activities.
  • Emphasizes the ease of mixing and matching different pieces.

9. Shopping for Casual Wear:

  • Advocates for online and in-store shopping for casual wear.
  • Mentions the importance of trying on clothes for fit and comfort.
  • Recommends exploring thrift stores and consignment shops for budget-friendly options.

10. Size Wise™️ Closet Coach:

  • Introduces an online marketplace and personal style coaching service.
  • Offers services like personal style consultation, online shopping, and closet assessment.

11. Don't Guess Casual Wear:

  • Encourages following guidelines to avoid guesswork in casual dressing.
  • Stresses the importance of looking polished without sacrificing comfort.
  • Recommends relying on Size Wise™️ for guidance in casual wear choices.

In conclusion, this comprehensive guide not only provides practical tips for dressing casually but also emphasizes the importance of personal style, occasion-appropriate choices, and the versatility of casual wear in expressing individuality.

How to Look Good and Feel Comfortable In Casual Wear (2024)
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