Dressing Up in a Casual Office

The casual office is always a bit of a challenge for me. I work with a nonprofit that serves young people mostly in their late teens and early twenties, and generally casual is an accepted form of dress around here. In my experience, however, whenever I dress “casually,” my height tends to skew me toward looking “childlike,” and it’s important to me that it’s clear, in my workplace, that I am an adult with responsibilities to the organization.

In the interest of avoiding the “adult who looks like a kid” image, I developed some simple rules that I now follow when dressing myself for work in the morning.  These have allowed me to feel like I’m dressed professionally while simultaneously allowing me to be comfortably in sync with my more casually dressed colleagues.  While I use these rules to dress up a casual office dress code, they can also be used as guidelines for dressing casually in a more corporate setting than my office.

Jersey: This is the PERFECT casual/professional material – but only if it is done correctly. Jersey-knit tees can be worn if they’re the right blend of fibers. Too much cotton and you risk looking like a teenager; too much silk and your shirt looks like lingerie. I’m a big fan of this shirt, and own it in multiple colors:

br luxe tee

Luxe-Touch Piped Tee | Banana Republic

This is one of the softest jersey knits I’ve ever found, and the satin-trimmed neckline dresses it up just a bit. It looks great with trousers, skirts, blazers, and cardigans.

Dresses: Dresses are the single easiest thing to ever wear. It is literally a one-piece outfit. The way you accessorize it determines how formal it is; a change of shoes can make a dress as easily ready for the board room as it is for happy hour.

I’ve sung the praises of Shoshanna before, and I’ll continue to do it here. They make incredibly flattering work-appropriate dresses in a variety of powerful colors, and every.single.time I wear one, someone comments on how fabulous I look. Full-price costs can be prohibitive, but they can be found through clearance and flash sales at J. Crew and Banana prices. Here are some of my favorites:


L to R: Delfina | Nicole | Shari

I own the green dress on the right, and LOVE IT. It looks great with simple accessories; it also looks great with animal prints and bling. Bold colors are your friend, people.

I also am a strong believer in the jersey wrap dress. Diane von Furstenberg, of course, is the undisputed queen of this look. Like Shoshanna, her dresses can be a bit too pricey if you pay asking, but eBay is a great source of DvF dresses at reasonable costs. Look at this beauty:


Limited Edition New Jeanne Two Silk Jersey Dress | DvF

Patterned wrap dresses really need no extra embellishment; I’d wear neutral shoes and drop earrings and let the dress do the talking.

Flat – But Polished! – Shoes: The best way to look overdressed in a casual workplace is to wear heels. The fact that I live in a pedestrian city certainly adds to this, but I can’t remember the last time I saw someone wearing heels in my office. I tend to wear polished flats with my outfits; they lend the professional look I crave without making me seem too dressy. Madewell is my go-to for great flats; the “Sidewalk Skimmer” is made of a beautiful leather that conforms to the shape of your foot and becomes the most comfortable shoe you own. The following two pair are on regular rotation in my wardrobe:


L to R: The Sidewalk Skimmer in Calf Hair | The French Knot Pointy Skimmer

Both useful neutrals (pro tip: animal print in neutral colors = neutral!) work with basically everything I own; the pointed toes grow up the look a bit, and the insole has a very slightly elevated heel, which makes my walking commute much more comfortable.

Satchel Handbags: Invest in at least one good satchel-style handbag, y’all. You’ll be so glad you did. Get it in a neutral color, and you’ll be golden for years to come. Unless you’re philosophically opposed, make it real leather (and if it’s “vegan” leather – AKA pleather – buy the good stuff so it doesn’t look too faux). Don’t get suede; it’ll fall apart faster than regular leather. Buy one large enough to carry files and a laptop, if you need to do that. You don’t have to spend a fortune to get a good bag, either. Check eBay and discount sites like 6pm and Last Call. Cambridge Satchel Company makes gorgeous, timeless cross-body satchels, and you can have them embossed with your initials! I’ve been wanting the classic Batchel for years:


Batchel | Cambridge Satchel Company

Miscellaneous Notes: If you wear trousers, make sure they fit well. Fit them to the biggest part of you (for me, my tush) and have the rest taken in. Same goes for button-up shirts. Don’t let them gap at the chest. Cardigans are polished without the formality of a blazer. Match your cardi’s neckline to the shirt you wear beneath it (v-neck shirt, v-neck cardigan; round-neck shirt, round-neck cardigan). For the love of God, wear flattering undergarments. And finally, always invest in quality items – the quickest way to look like My First Job Barbie is to wear cheap-looking clothes.

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