Living the good life + Fighting the good fight

Tips on Dressing Professionally & Comfortably

As you may or may not know, I have a day job, a regular ole 9-5. I work in a university’s development and alumni office as a writer. I sit at my desk in front of my computer or laptop (sometimes both at the same time) for most of my work day. I have to dress professionally, but there are some times where I get to dress more casually or more formally when I am working from home or working at an event.

I have been in an office environment for almost six years and over those years, I have worked hard to find clothes that are professional and comfortable that I can wear to work. It was no easy task because I also wanted those pieces of clothing to be, dare I say, cute. But, I have collected a good amount of items that fit that bill and I continue to collect those pieces.

Before I get started, I want to give a shout out to my sister from another mister, Abigail, who suggested I write this post. Game on. Here we go.


Tip #1: Invest in comfortable and durable shoes. This is no joke because heels are modern torture devices and flats become worn within seconds it seems. I would recommend finding flats, slip-ons and booties that are comfortable and appropriate for work. (I am wearing a couple of my favorites in the photos below.)

Unfortunately, I can’t recommend a ton of brands for this one because I think shoes are very personal and comfort-level can vary from person to person. I have heard great things about Rothy’s, which are sustainable, and Tieks. I will, however, recommend TOMS to anyone I meet. I have several pairs and will continue to buy them.

Tip #2: Get some stretchy pants. I’ve talked about this before and I will never stop talking about it. For me, if I am not comfortable, I won’t be able to focus and I will be irritable. Stretchy pants are KEY to my success. The secret to maximum comfort and productivity is finding pants that feel like leggings, but look like slacks or trousers.

Here are some key words to look for when you are online shopping for stretchy pants: stretch (obviously), pull-on, spandex, comfort-fit and jegging (just watch your fabric, it could be too casual). “Pull-on” is an important word to look for because it means there are no buttons, zippers or clasps of any sort, which means nothing will be digging into you.  In person, look for classic patterns, like stripes, polka dots and checks, and look for fabrics that mimic slacks and trousers, but have added stretch.

I have amassed quite the collection of work-appropriate, stretchy pants that I live for and recommend to everyone. (I need to look into men’s stretchy, work pants. I don’t know if they are a thing, but I think they should be.)

Outfit Details: White blouse – Thrifted | Pants – Thrifted | Flats – TJ Maxx

Tip #3: Get some flowy pants. Similarly, to stretchy pants, flowy pants just add a level of comfort to an outfit that we need for a long work day. These sort of pants have many names, so it is even more important to look at the fabrics and how the pants hang off of you.

When my clothes are tight, I sometimes can be more anxious than normal, so I have fallen in love with the flowy pant and will continue my love affair with them until the end of my days. No lie, my favorite ones (pictured here) feel like pajamas.

Outfit Details: Pants – ASOS | White tank top – Target | Necklace – Target | Shoes – Thrifted, TOMS | Denim jacket – Thrifted

Tip #4: Collect t-shirt dresses. If you are more of a fan of dresses or get tired of wearing pants, look for t-shirt dresses in minimal prints and in every color. I don’t need to say it, but I will. T-shirt dresses are long t-shirts! They are the ultimate move in classy comfort.

These can also be flowy and can have varying sleeve lengths for different times of the year. You can also easily layer cardigans and jackets over a t-shirt dress.

These are fairly easy to find, but Target, Boden and Talbots are good places to look.

Outfit Details: Dress – Thrifted, Old Navy | Cardigan – Target | Boots – Thrifted, Carlos Santana | Earrings – RhodArts, bought at The Lady Jane

Tip #5: Seek out good fabrics. I think you know by now that stretch is key. But, you should also seek out soft and breathable fabrics. Some professional clothes are made out of stiff, no stretch, thick fabrics that make my skin crawl. Don’t be afraid to touch the clothes in the store and, obviously, try them on. And when shopping online, take a look at what the items are made of and do some Googling if the material isn’t one you are familiar with.

There are other items of clothing that I don’t particularly wear often that can fit into a comfy, but professional lifestyle, so be sure to consult the fabrics of an item to see if it will work for you.


I hope this post has convinced you to maybe donate or sell some of your uncomfortable work clothes and begin a search for more comfortable options. Those options are out there! You just have to look for what you feel the most comfortable and confident in.

It has been said that life is too short to wear boring clothes and I will add that life is too short to wear clothes that are uncomfortable.

1 Comment

  1. Suzanne Cole

    Another great blog!! I agree with every point!

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