25 outfit ideas for what to wear to the office

Getting dressed is supposed to be fun! Given that most of us have to get dressed for work more than anything else, figuring out what to wear to the office should be especially fun.

It’s usually not, though. Office outfits tend to be utilitarian, practical.

But my friends, practical does not mean plain. Here are 25 outfit ideas to try, so you can feel happy and confident everyday…yes, even on Monday mornings!


try upgrading your accessories

chevron tote from Holland Cox with leopard print accsesories
A plain bag is not as practical as you think. What use is something that makes you blend into the background? How can you feel happy and confident while you’re invisible?

The cassandra tote is a significant upgrade to the plain brown or plain black briefcase…big enough to carry all your work gear, but interesting enough to make sure all eyes are on you…right where they belong.

You could wear a plain brown belt and plain brown heels…or you could upgrade to an eye-catching leopard print!  Mixing prints is an awesome way to stand out, and it works in this case because the color scheme is the same.

(Subscribe to the Insider’s List to get more advice on how to mix prints.)


try dressing up a denim mini skirt

metallic leather wrap belt from Holland Cox with a denim skirt
You might think you can’t get away with a denim mini skirt in the office…but it’s all in the styling.

The jezebel wrap belt is bronze metallic leather, and can upgrade pretty much anything you wear with it! Along with great jewelry and a serious tweed jacket, your denim mini is ready for 9-5. The fact that everyone will be jealous that you can “pull it off” is just a bonus!

(Also shown: the anjelica 517 tote.)


try wearing your off-season clothes

Holland Cox infinity scarf with a sleeveless top
I never put away my clothes when the seasons change, I just re-style them for the new season whenever I can! This sleeveless blouse doesn’t need to be exiled to the back of you closet, you just need something warm to wear with it.

The naomi infinity scarf is lined in warm cotton flannel. It can give your outfit both a season-appropriate upgrade and a style upgrade with it’s bright and bold print, and subtle shine.


try bold graphics

the anjelica tote from Holland Cox with a striped blazer
This is the type of jacket you see in the store and love it, but then don’t get it because you think it’s not “practical.”

But, practical does not mean plain. In reality, boldly printed pieces like this are the perfect upgrade for all the plain things you already have!

A jacket this awesome effortlessly upgrades all your plain black (and gray) skirts and pants.

(Also shown: the anjelica 517 tote.)


try a denim dress

Holland Cox button scarf with a denim dress

The secret to wearing denim at the office is to pick a dark wash, a tailored silhouette, and of course, the right accessories.

The katherine button scarf is just such an accessory! The subtle black and gold print is sophisticated enough to elevate any denim dress…when paired with beautiful jewelry (yes, you can wear a necklace with a scarf!) and gorgeous boots, you have an outfit worthy of any c-suite.


try contrasting textures

the anjelica tote from Holland Cox with a leather skirt

A tweed jacket is a professional wardrobe staple! Whether yours is colorful like this one or more plain, it can benefit by being paired with contrasting textures.

That’s why I chose to style this one with a leather skirt, and the denim and vinyl anjelica 517 tote. Even in so-called “neutral” colors, the contrast elevates the outfit into something interesting rather than ordinary.


try a little edge

Holland Cox tote with leather and leopard print

Now here is a way to make sure every eye is on you! Leather and large-scale animal prints are guaranteed to be eye-catching, even in the most creative and fashionable offices.

Good thing you have a great statement bag like the cassandra tote to stand up to such a bold outfit – anything less would just be a waste!


try upgrading your plain trousers

the anjelica tote from Holland Cox with camel trousers

You probably already have a good pair of trousers in a color you thought was “practical” when you bought it – camel, gray, navy…et cetera. Instead of putting on a plain white blouse, why not pick a bright color?

Instead of a plain bag, why not something with more presence and style? The anjelica 517 tote is dark blue denim with classic gold stitching, perfect to set off your CEO-worthy jewelry, and upgrades your entire outfit instead of bringing it down.


try high style denim

high style denim

You’ve probably noticed I love designing and making with denim…I just love how versatile it can be!

This outfit is an excellent example. Stella McCartney trousers, Louboutin booties, and very expensive designer jewelry look great together, and are perfectly set off by the denim and vinyl anjelica 517 tote – but only because of it’s unusual style, classic stitched details, and bold red accents. A plain denim bag could never do that!

(Stella would definitely approve of the vinyl on the back!)


try mixing warm and cool together

the sofia tote from Holland Cox with a plaid skirt

The sofia 517 tote is a mix of black, gray, and bright blue, so you might think that only cool tones could be paired with it.

This delightful plaid skirt proves that a warm gold can fit in just fine! Don’t be afraid to mix tones like this, especially if you have a spectacular piece (like the skirt or the necklace) that does all the heavy lifting for you.


try metallic leather

metallic leather wrap belt from Holland Cox with a gray skirt

What could be more deadly boring than a plain gray skirt and a plain white sweater? This is not an outfit that says “I’m the boss,” or that is likely to make you feel confident enough to take charge.

The sheba wrap belt is the perfect upgrade – pewter metallic leather means that it can make even the plainest outfit into something extraordinary.

Pearl jewelry and the eye-catching gloria tote (with a hand-drawn mandala motif) completes the look. Your plain sweater has never looked this good!


try wearing the color of the year

the raina crossbody bag from Holland Cox with a ultraviolet blazer

According to the Pantone people, ultraviolet is the color of the year, and you have to know that I’m thrilled by this. Purple (in all its manifestations) is always going to be one of my favorites!

The raina crossbody bag is a great way to wear it! Even though you’re going to see ultraviolet everywhere this year, you probably won’t see much of it on metallic leather, and certainly not on a bag as practical and useful as a crossbody…it easily fits inside your briefcase or tote bag, and seamlessly transitions to your weekend outfits, too. What’s more practical than that?


try adding stripes

the trinity bag from Holland Cox with a striped blazer

I’m a firm believer that stripes go with everything, and that black and white stripes in particular are a great way to break into wearing prints…a gateway drug, if you will. An easy, painless, and fool-proof way to make any outfit more interesting.

And here’s the proof: this striped blazer will go with literally everything you already own…it’s just like wearing a solid black or a solid white blazer, only much more interesting!

The trinity everyday bag matches this purple sheath dress exactly, but is certainly interesting enough to stand on it’s own (more on that, next)…you could really wear this outfit with any color dress!


try letting your bag be the star

the trinity bag from Holland Cox with a striped dress

A bold color-block bag like the trinity everyday bag is the perfect type of bag to be the star of your outfit – it almost doesn’t matter what you wear with it. Especially if your closet is already full of lots of red and purple, or full of lots of neutrals…it will work either way.

That’s the benefit of finding “your colors” and sticking with them…you can find bold and bright accessories that work with your entire wardrobe!


try wearing red

the moira tote from Holland Cox with a red sweater

I know you already have a black pencil skirt. Instead of pairing it with something else “neutral,” why not bright red? There’s nothing like a deep, saturated red to make you feel confident and fearless!

The moira tote is mostly black and white, but has some red accents that make it a perfect accompaniment, and certainly more interesting than a plain black bag.


try wearing a necklace with a scarf

the cassandra scarf from Holland Cox with a long necklace

The secret to styling a necklace and scarf together, is to make sure both can be seen. That means with an infinity scarf like cassandra here, you need a long, pendant-style necklace.

With a longer scarf, you might want a shorter necklace that follows a the line of a crew neck, or even a choker. Don’t be afraid to experiment!


try a monday dress

the moira tote from Holland Cox and a Monday dress

The “Monday Dress” is the dress you can wear without thinking about it – it fits like a dream, it’s your favorite color, and you always look great in it. That’s what makes it perfect for Monday…painless, effortless, and foolproof. Everybody needs a Monday Dress!

Even if your Monday Dress is not red, you need an awesome bag like the moira tote to go with it. The whole point of the Monday dress is effortless style. A plain, boring bag just isn’t good enough for the kind of impact you need on Monday mornings!


try a maxi skirt

the rosetta scarf from Holland Cox with a maxi skirt

Even though I’m short, I love to wear maxi skirts! Even one with a dramatic, full silhouette like this one can be appropriate for the office, especially if it’s in a sober and traditional tweed, or a classic print like windowpane check.

I know you’re afraid to wear so much skirt with anything but a plain black top, but that’s okay. To keep warm, and to add a little something special to your outfit, try a boldly colored scarf like the rosetta button scarf  – a tonal print is always going to be easier to wear than a multi-colored print, and the traditional roses pair beautifully with the classic windowpane check.


try a button scarf

the natalie button scarf from Holland Cox for the office

The button scarf really is the best type of capsule accessory…that is, the type of accessory you add to your capsule wardrobe to make it more versatile and interesting! It can be worn in so many different ways, that it’s like having several accessories in one.

The natalie button scarf in particular is great. The book marble print is subtle but interesting, and easily works with so many of your neutrals: gray, black, white, and navy.

(Also shown: the gloria tote.)


try upgrading your gray

the sofia tote from Holland Cox with gray pencil skirt

It’s so easy for gray to look faded, dingy, or boring…and I’ve already shared several ideas on how to avoid that.

Whatever strategy you choose, you’re going to need a great bag, and the sofia 517 tote is perfect. Subtle color and an interesting silhouette save the day!


try adding texture

the sibyl bag from Holland Cox with a ruffle blouse

The sibyl everyday bag is a great example of how texture adds interest and style. The black stitching and the red ultrasuede turn the plain gray denim into something extraordinary.

The same can be said of the red blouse – you could wear something plain, but pleats, ruffles, embroidery, or other surface design are so much more interesting, and will guarantee you won’t look like everybody else!


try a bold print

dragon print button scarf from Holland Cox upgrades a plain office outfit

The lucille button scarf pairs an extremely bold dragon print in black, white, and gray with bright red for a truly unique accessory. It is the perfect upgrade to a plain black skirt and a plain gray blazer.

Without the scarf, this is the type of outfit that will have people mistaking you for hotel staff, instead of recognizing you as the keynote speaker.

(Also shown: the moira tote.)


try a sweater dress

the sofia tote from Holland Cox with a sweater dress

Like the Monday Dress, a sweater dress is a great short-cut to an awesome outfit. If your sweater dress is a tad too casual for your office, adding a jacket with stylish lapels is the easiest way to upgrade.

Sophisticated jewelry and a great bag like the sofia tote finishes the look. Now you’re dressed to impress!


try a bright color

the sofia tote from Holland Cox with bright blue pants

Even if you’re brave enough to regularly buy bright colors, I bet you rarely think to try brightly colored pants.

But they’re really not any harder to wear than anything else…I know you already have a ton of black tops to wear with them (don’t lie!). Add some stripes and a great bag like the sofia tote,  and you’re guaranteed to stand out from the crowd of gray trousers and black pencil skirts.


try mixing prints

how to effortlessly mix prints with Holland Cox handbags and accessories

Wearing a print is a great way to upgrade your outfits, but mixing prints is definitely the next level.

The absolute easiest way to do this, is to keep a tight color palette. No matter the scale or the nature of the motifs, you’ll always look put together. In this outfit, the fitzgerald button scarf ties all the colors together, and keeps you warm, too!

(Also shown: the the sofia tote.)


I hope I’ve inspired you to experiment with your wardrobe, and try upgrading the outfits you already have with some awesome accessories.

Need some inspiration? Subscribers to my Insider’s List get a series of posts on style experiments to try, including ideas on how to find “your colors,” how to mix prints, and much more. Click here to subscribe.





2 thoughts on “25 outfit ideas for what to wear to the office

  1. You’re doing such a great job. I wish I was out in the work force
    Again. For you to be stylists. You get that from your mama. Proud to see
    doing well. Keep up the good work.
    You go girl!!!!

    1. Thanks Patsy! I love that you love my outfits, but I’m sure you come up with pretty awesome ones without my help! 🙂

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