Some of you have asked for tips on how to dress casual and comfortable for work.

Although it is difficult to give guidelines that are suitable for all jobs or dress codes, let’s look at some outfits that are casual and comfortable but still look professional enough for work.

Since comfort is key, we will look at outfits that are easy to wear and look great with flat shoes.

When creating these outfits I especially thought of the job of a teacher. As a teacher you will want to look current, youthful and hip, but also smart and confident. As you are on your feet a lot of the time, shoes need to be comfortable.

Option 1: pants, shirt and jacket

You can’t really go wrong with this combination. You could make this outfit as casual or smart as you like. My version is quite casual as I’m wearing stretchy skinnies and wear my shirt over my pants. The outfit will get smarter if you tuck your shirt into your pants and wear straight full-length fitted jeans instead of cropped skinnies.

If you want to look a bit smarter and more professional then adding a jacket to any outfit will do the job!

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Want a bit more edge? Add a funky necklace or play with asymmetrical elements in your outfit.


Don’t think you can just use a blazer style jacket. Other jackets can work just as well.

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Option 2: pants and shirt

This outfit option is super comfortable. It looks dressier and more professional when you tuck your top into your pants. You can add interest with a nice necklace or other accessories.


Make your outfit a bit hipper and professional with current shoes. These pointy flats make all the difference in this outfit.

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This style is more casual and does not really give you a lot of authority. On some days you may just want to be more casual though.

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Option 3: Skirt and top (jacket optional)

Both straight and a-line skirts can work well as comfortable outfit choices for work. If you want to be comfortable in your straight skirt, make sure that you choose a stretchy fabric. A skirt looks chic and professional when combined with a button down shirt but can also be worn with a hip t-shirt as shown below.

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A-line skirts are very comfortable to wear too. I have combined it here with a warm woollen top and the scarf adds more professionalism as well as color to the outfit. Although this particular skirt can be worn with booties, many A-line skirts will look better with ballerinas or pointy flats (as well as heels of course).

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Like to add a bit more edge to your outfit? Choose a non-standard skirt with a drape.


Option 4: a dress

A dress can be a good casual option. Choose a lose fitting dress in a stretchable fabric for extra comfort. This dress is worn with comfortable wedges but would look equally good with red flats.

Another great option would be a wrap dress with sleeves.

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When browsing through my outfits for examples for this article, I realised that I could wear almost all of my outfits if I were a teacher.

However, if I wanted to feel more professional and authoritative, yet still comfortable on any given day, I would opt for outfit formula 1 with a well-fitted blazer in a good fabric.

For more ideas on dressing casually smart, check out these 7 casually smart dressing formulas. Many of the examples shown there would work well for teachers too. Also check out Dawn Lucy who is a high-school teacher and always looks casually chic!

How would you dress in a casual and comfortable way if you were a teacher?


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