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How to Dress Comfortably but Still Look Stylish

Trying to stay comfortable while dressing stylish can be a challenge and finding trendy comfortable clothes can be even harder. While it may seem impossible to find chic outfits that feel just like your PJs, there are some ways you can make your comfy clothes more stylish! 

You Can’t Go Wrong with Black 

From black leggings to a black jacket and even black accessories, black creates a chic look. Black goes with everything and the right shade of black will set your style off! When you choose black clothes, it’s important to make sure the black is rich, deep, and not too faded. It’s also important to find a black that will last for a long time. 

Accessories Change the Outfit

No matter what you’re wearing, the right accessories can have a huge impact on the clothes you’re wearing. A simple t-shirt and jeans can be dressed up with the right necklaces, shoes, or even a trendy scarf. There are so many ways accessories can help you take your comfortable outfits into an entirely new territory of style.

Be sure to choose your accessories intentionally. Plan your comfortable outfit, then pick out the accessories you want to pair with it. Choosing accessories that you love will allow you to feel empowered and chic when you’re rocking your new favorite outfit.

A Structured Jacket is Stylish

Jackets that have a lot of structure can help add interest and a stylish accent to your outfit. Try throwing on a leather jacket with your t-shirt and legging combo or add a blazer to one of your already favorite pieces. The jacket not only helps you look more stylish but it can also help you stay warm if it’s chilly out. 

Make sure to try on different structured jacket styles. You may be surprised to find that many of them are actually very comfortable! 

Consider the Materials 

Some materials provide more comfort than others. While a pair of wool pants are a great way to look put together (and stay warm), it may not be the best material when you’re trying to stay comfortable. It can be scratchy and difficult to wear, especially in the warmer months. If you want an option that’s similar in structure, linen is a great lightweight option and looks just as stylish as wool pants. Alternatively, many fashion brands are now offering pull-on work pants and denim with sleek, ease-of-wear in mind.

Go for materials that are soft, have a bit of give, but still maintain their shape throughout the day. Adding pieces that are made out of the most comfortable materials can help you stay comfortable and will be great for any type of event that you plan on attending. 

Try a Trendy Staple Piece for Comfort

Trendy staple pieces are the best way to ensure you look stylish and stay comfortable. If you wear these pieces often, you will get used to them and they’ll be easy for you to wear. They’ll also become something that you can feel better in no matter what you’re doing. Adding something like a graphic tee to your collection will allow you to always look trendy and be comfortable. Graphic tees are always in and have stood the test of time. Pair your tee with a blazer or a structured sweater. You can also pair it with a pair of casual dress pants for a look that’s unique and stylish.

Long Layers Add Coziness

Fans of layering up love the convenience of being able to change the look of an outfit throughout the day. Layers are also great for areas where the weather may change unexpectedly or when you might need to shed a part of your outfit for more comfort. While layers added on top of each other without much depth can tend to look sloppy, playing with long layers – like an open cardigan over your favorite top – can counteract the bulky look. Long layers are the perfect option when you’re trying to look and feel your best.

Be Wise About Shoes

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The shoes can make the outfit and that means you must find something that’s stylish and comfortable. While wearing your worn-out pair of Birkenstocks or Uggs every day might seem like the comfiest option, you’d probably get some looks and a visit to HR if you wore them to your business casual nine to five job. Ballet flats look stylish and are more comfortable than some of the other options on the market. 

Need to dress it up a bit more and wear heels? Go for a chunky or platform heel. They take some of the pressure off your feet while keeping your outfit streamlined. Or, invest in some designer sneakers for a playful, sporty, but elevated look, as you can find designs with leather materials or other touches that take up the old school sneaker-look up a notch. Booties are the latest style, perfect when paired with some cuffed denim and one of those aforementioned cozy, comfy long cardigans.

Revamp Your Work Attire 

The outfits you work in should look great and feel comfortable. You need to present your best self while you’re on the job, but that can be hard to do if you don’t feel comfortable. Instead of wearing the same uncomfortable clothes to work every day, consider swapping out a few of your pieces at a time for more comfortable versions. Paper bag waistband pants, chunky heels, and linen blend shirts are all comfortable and professional! 

Whether you’re looking for an outfit that’s perfect for travel, one you can wear to work every day, or if you just want to be more stylish, there are ways you can do it comfortably! 


Becky Paulson comes from a long line of educators. After graduating from college with an art degree, she realized that the classroom was not her canvas. Instead, she walked the path of fashion retail, falling in love with texture, color, and style. When her family started growing, she opted to sell clothing at festivals. After her children became adults, she found A Corner Cottage https://www.shopacornercottage.com/, a gift shop owned by a childhood friend, and she began selling her clothing. This stage in her life signaled a new beginning for her artistic sense, resulting in opening A Corner Cottage, Too, a place for women to gather and find the perfect clothing designs for their lifestyle. She feels blessed and inspired by her customers and friends. Becky loves sharing her knowledge and passion for fashion with women seeking more meaningful ways to dress.

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