The 12 Best and Most Comfortable Work Dresses: Back to the office

From my last post featuring the best work dresses from Amazon, it is clear a lot of women are on the hunt for not just work dresses, but comfortable work dresses, seeing as so many of us are returning to the office this Fall.

This time, I decided to expand my list to include not just Amazon work dresses, but other brands as well, with most items currently on sale.

These dresses work for different body types and the best part is they are all under $100!

You may have gotten accustomed to the comfort of sweat pants, leggings, t-shirts or even pyjamas (hey, no one’s judging) while working from the solace of your home. Heading back to the physical work environment does not mean you have to sacrifice comfort in order to look work-appropriate.

Whether you’re looking to incorporate more of an athleisure aesthetic, like that of Athleta, or believe in serving more corporate looks each time you set foot in the office, this list should serve as the perfect balance with inspiration for all who love a good comfortable dress.

Gone are the days when the work wardrobe consisted of stiff pencil skirts and uncomfortable shift dresses. After the pandemic, our new normal sees the professional look featuring more comfortable work clothes.

For this list, I picked versatile pieces that could serve dual or even multiple purposes; from office to brunch to yoga class to cocktail hour. In this economy, the last thing you need is a non-versatile work wardrobe and so you want to make sure you’re getting a bang for you buck whenever you’re shopping for clothes.

Soft materials, a more comfortable fit and affordability are at the heart of this non-exhaustive list.

First up, we have this great Walmart (yes, Walmart) pleated midi dress.

I love that it’s plus-size friendly and could be dressed up with some heels or dresses down with some slides or flats.

The flowy silhouette of this lightweight dress makes it flattering and comfortable while keeping it a professional attire.

Dress – HERE
Loafer slides – HERE

This Gap denim dress could be mistaken to be meant for casual outing sonly but think again. If your office has casual Friday’s, then pairing this dress with some leggings would keep you casual, comfortable and work appropriate.

During the warmer months, you could pair it with some light cotton leggings and sneakers while leather leggings and boots could be worn during the colder months.

Dress – HERE
Shoes – HERE

With Summer not quite being over, the next two dresses are great options for the warmer weather and even early Fall weather if you decide to style them with some boots and leggings.

If you are also someone who sweats a lot, cotton and linen fabrics such as those featured in the dresses below are your friend.

I love both of the featured sleeve lengths – the long sleeves are great for women not comfortable showing their arms in the workplace while the short puff sleeves offer a relaxed fit; more on the casual side.

Yellow Banana Republic dress – HERE
Brown dress – HERE
Boots – HERE

Another great Summer/Fall transitional dress is this white Old Navy shirt dress featuring side splits. It works well for both seasons as you can wear either leggings or leather pants underneath along with loafers or boots.

This outfit would also work well with ballet flats or even a pair of pumps. An oversized blazer or leather jacket could be added to the look during the Fall or colder months.

Shirt dress – HERE
Leggings – HERE
Loafers – HERE

If you’re still transitioning from comfortable loungewear to full on business casual office looks, this short-sleeved midi dress is a great option for you.

Pair it with longline cardigan during the Fall or if the A/C is on full blast in your building. Who said office wear had to mean black dresses and uncomfortable pantsuits?

It comes in both regular sizes as well as plus-size.

Dress – HERE
Cardigan – HERE
Loafers – HERE

If you commute to work via public transportation or walking, you may be wondering what types of outfits could be comfortable not only at the office but also during your commute.

Sweater dresses are your answer to that! I love the variety of colors as well as the length that this style comes in. They would be easy to walk in but still a great length for the office especially as a part of your Fall wardrobe.

A sweater dress is one of those things that can be work to both casual events as well as a board meeting. It just depends on the length and design.

Rust dress – HERE
Green dress – HERE
Boots – HERE

As I had previously mentioned, Athleta is a great brand to go to if your style is more leisure or athleisure.

The fabrics used are more lightweight and the styles are simple. It’s all about comfort.

This dress is a great example of how Athleta takes a modern twist on athleisure in the workplace. You

This shift dress could go from office to date night by switching the loafers for a pair of pumps.

Dress – HERE
Loafers – HERE

Another great Fall dress option is this midi belted dress in a beautiful burgundy colour and featuring side pockets.

With comfortable ankle boots or flats, it would make for a great work dress.

Dress – HERE
Boots – HERE

Another Atheleta dress makes it to this list and with good reason. This midi length long-sleeved shirt dress comes in different colors and is a great dress to take you from the office to an outdoor lunch and even Happy Hour.

At time of publication of this post, other color options are available.

Dress – HERE
Flats – HERE

I love this next dress for its more feminine cut, its softness and curved waist which hugs your curves in the right places. Oh and did I mention it has side pockets?!

You could add a blazer, light jacket or longline cardigan to the look to take it up a notch.

Without a jacket or blazer, this same dress could be worn to the grocery store and some more of your favorite places thanks to the jersey fabric and more casual nature of the dress thanks to the short sleeves.

Dress – HERE

The elastic waistband also allows room for post-lunch bloating. (No one’s judging!)

I hope you find this list of comfortable dresses very useful and a reminder that you can still be comfortable and chic at the office.

If you are starting a new job and just building your office wardrobe, then I always suggest you start with a few pieces in a neutral color. Confirm what your office dress codes are before going out and splurging on 6 inch heels and 5 pairs of j. crew pants.