Tips For Wearing Skirts to the Office

When I worked in a creative office I loved wearing skirts because I always felt polished, feminine and comfortable. They also gave me endless amounts of outfit ideas so I never got bored getting dressed everyday. It was a Win – Win! But I remember a very stylish co-worker telling me how envious she was of my skirt outfits because she didn’t know how to pull them off. I was so surprised someone so fashionable and chic didn’t feel comfortable wearing skirts! I understand that it’s a bit more complicated to pull together since it’s two pieces instead of one (aka dress or jumpsuit) but that’s where the fun comes in! So in the blog post, I pulled together by favorite past skirt looks for inspiration and my tips to pulling off skirts looks for the office!

#1 Tip: Always go for a knee or mid-calf length!

Disclaimer: I only worked in a “creative” office so I had a lot of leeway in what I wore. So these looks are best for those that have a casual or smart-casual dress code.

Tip #2: Fun prints in classic silhouettes add a playful touch to a traditional outfit.

A button down shirt and slip style skirt are very classic “work” silhouettes. While an all black look can be very chic, it can also appear stark and can get boring really quick (at least for me!). So instead look for these styles in fun prints or colors – like I did here for an animal print skirt and gingham trimmed shirt. Kept the shoes, bag and jewelry classic to not overdo it. If you can get away with it, I love tying a button-down top to juxtapose the overall sophisticated aesthetic. It’s that unexpected touch that gives an outfit style. But if you don’t feel comfortable doing that, then a simple tuck will look great too!

Outfit details: Vintage Blouse from Redkey Threads (sold), Thrifted Skirt, Heels from DSW, Vintage Purse, Free People Sunglasses

Tip #3: Layer a collared shirt under a tee for a more polished look.

And when paired with a pleated skirt and closed toe heels, the tee becomes more sophisticated while still looking effortless.

Outfit Details: Thrifted Tee, Collared Shirt from Joe Fresh, Old Zara Skirt, Vintage Heels, Thrifted Straw Bag, Thrifted Vintage Belt, Vintage Sunglasses, Vintage Earrings

Tip #4: Dress up a denim skirt with a extra fancy top.

By pairing something ultra fancy, like a ruffled blouse, with something really casual, like a denim skirt, you end up somewhere in the middle and that wear “smart casual” lives.

Outfit Details: Vintage Blouse from Redkey Threads (sold), Vintage Denim Skirt, AE Sandals, Vintage Belt from Redkey Threads, Vintage Crochet Bag from Redkey Threads

Tip #5: The easiest outfit for “casual friday” is a tee and midi skirt.

I’ve said this before and I’ll say it again – a tee and midi skirt is the most versatile outfit combination. It can take you everywhere and anywhere – even on the red carpet! A feminine midi skirt instantly adds sophistication so even when wearing it with a tee and sneakers, you’ll still look polished. But ultimately, its still just as comfortable as jeans and a tee!

Outfit Details: Vintage Tee, Vintage Skirt from Redkey Threads, Vintage Straw Bag from Redkey Threads (sold), Thrifted Vintage Sandals, Gap Sunglasses, Vintage Earrings


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