Work Outfit Ideas: Five Simple Chic Ideas

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Getting dressed for work should be an exercise in fun — that’s what I believe! These days I work in a casual office which means I could go to work in jeans and a tee shirt everyday if I wanted to, but mostly I choose to look put-together and one step above casual.

With that in mind, this new series will be focusing on easy work outfit ideas spanning my personal aesthetics — preppy chic (classic tailoring with elements of color and boho), modern femme aka new romantic (soft touches of pastels and lace details mixed with neutrals in modern cuts) and boho chic (boho elements mixed with urban modernism).

Don’t know what any of that means? No worries, just look at the pretty outfits in this post and see if there’s anything you like. You can see all the posts in this series by checking out my work ready tag. These outfit posts take a long time to put together — several hours or days as opposed to just a few that other posts take, so this series will not run regularly. The effort is full but worth it for the fun!

This particular post features mainly looks with jeans, because jeans can be a lot dressier than they used to be. Here in New York distressed denim is having an interesting moment at work where you’ll see crisp shirts and blazers mixed with destructed denim and pumps, creating a visual mix that communicates “I’m serious about my job…but not too serious.”

The outfit above, featuring the Cameron slim crop pant ($80), looks dressy but features casual elements in it like the Tie-sleeve sweatshirt ($53). Using classic finishing touches like the Elsie suede pumps ($245) grounds the look even with the trendy sleeve of the sweatshirt. In two colors, this neutral work look communicates competence, confidence and an appreciation for the classics.

Next up, we have a look with some masculine elements and some feminine elements. It all begins with the Thomas Mason® for J.Crew boy shirt ($128), a very crisp white buttondown that features huge cuffs. Buttoned up, these cuffs could easily pass for a men’s shirt. But with the cuffs unbuttoned and freely open, they look more like the trendy bell sleeves we’re seeing everywhere these days — a decidedly feminine touch.

Other feminine touches in this look include the very Audrey-esque 10 percent deck turtleneck in stripe (now $50) and the Audrey flats in suede (now $104). These are then again challenged by the masculine cut of the New easy pant in matte crepe ($90). I would personally complete this look with a big necklace like the Beaded double strand necklace (now $95).

Those are a couple of retailer takes — now here are some of mine.

This is a pretty typical work look for me above — simple, neutral tones with a mix of layers for Fall. Keeps me warm in the office and cool outside. The cardigan is just a drop longer than the halter top — the ideal proportions for layering in this case.

Outfit details:
Open cardigan sweater ($55)
Patterned halter tank top (now $25-$35)
A-line denim skirt ($42)
Coco leather ballet flats (now $45-$54)
Crystal bubbles necklace ($25)
Ryann crossbody bag ($55)


Another layering trick for me, especially with dresses, is to layer a white dress shirt underneath them. This can make a casual dress more office-friendly and allows for quick changes once the workday is over. A pair of dressy smart flats make this outfit seem especially polished.

Outfit details:
Oxford shirt ($35)
Fatigue shirtdress ($65)
Braided cotton belt ($28)
Edie Leather Loafers ($76)
Tortoise link necklace ($30)
Shoulder strap tote ($69)

The last three outfits in this post all build upon jeans. In this look I’ve chosen a printed top with double ruffle sleeves for some playful accents, and then kept the rest of the look very neutral so as not to be too loud. Comfy flats in one of the colors from the top make this look seem well thought out, and the deep red bag is one more touch of color to capture interested eyes as I walk to and from the subway or lunch break.

Outfit details:
Printed double ruffle-sleeve top ($45)
Rinse wash midrise skinny jean ($55)
Beaded oval dangle statement earrings ($28)
Zoe suede d’Orsay flats ($63)
The Small Transport Crossbody ($128)


Above is a work outfit where the ultra-casual destructed boyfriend jeans are paired with feminine, dressy elements to elevate the overall look. I never get sick of pink or tortoise! A flattering lace top is a key piece to have in your work arsenal — it can go with so many things.

Outfit details:
Cotton Caryn cardigan sweater ($30)
Lace T-shirt ($25)
Colorado wash boyfriend jean ($65, size down)
Isabelle suede pumps ($71)
Gold link bracelet ($20)
Tortoise link bracelet ($21)
Small Zip Pouch ($23)


This last outfit takes one of my favorite tops for all things — the striped boatneck — and dresses it up just a bit for work. Stripes on stripes via the blazer is a bold statement, but the Chanel-esque look of the blazer and its darker colors keep the overall look toned down (and you can easily swap in a solid blazer if you prefer).

A low, classy heel, sparkly earrings in a subtle neutral and a bag that pulls out one of the accent colors from the striped blazer complete this fun office chic look.

Outfit details:
Striped boatneck T-shirt (now $25)
9″ high-rise toothpick jean ($110)
Beaded ball earrings ($65)
Tweed Lady jacket with ties ($198)
The Ella Pump ($128)
The Medium Transport Tote ($158)

I don’t plan on repeating items in my outfit suggestions, but that doesn’t mean you shouldn’t! The glorious thing about these looks is that the items in them can be mixed and matched with each other…perhaps I will do an outfit remix post.

What are your work staples right now?


  1. Maggie
    August 21, 2017 / 10:57 am

    These are great ideas: I especially love the last "stripe on stripe" outfit idea! I love how you have highlighted such budget friendly items from J Crew Factory since I am sometimes overwhelmed by the choices there. I have been happy with the quality when I have visited the stores and am looking forward to checking out some of these combos especially with flats.

    • August 22, 2017 / 1:14 pm

      Thank you Maggie! I too like J. Crew Factory, though personally I have found the quality to be hit and miss. The items in this post are all things I've tried on or own so I know they are at least decent quality.

  2. Christina N.
    August 21, 2017 / 7:46 pm

    I echo Maggie's appreciation (again! ;))–thank you, Roxy, for picking out J Crew Factory items. I basically just purchased the entire first outfit (the one with the gingham halter top) and the loafers from the second outfit. To add to Roxy's most helpful post, for today only, everything is 50% off at J Crew Factory (prices as marked), and if you're a teacher or student, you can get an additional 15% off (this coupon can be combined with the 50% offer; I just did it!).

    • August 22, 2017 / 1:14 pm

      Yay!! I hope you love it Christina N, I'd love to hear how everything works out for you.

      Thank you much for sharing that awesome promo!!

      Also I want to mention that for anyone looking for super cute stuff on a budget, I love Kimberly of Penny Pincher Fashion. Although her body type is quite different from mine I often find really good outfit and accessory ideas from her inspiring posts.

  3. Kelly
    August 22, 2017 / 8:39 am

    I love each of these looks, especially the accessory suggestions. I tend to be lazy with switching out my bags and jewelry, and this really illustrates how a fun necklace or colorful bag can really bring an outfit together. I especially love the distressed jeans and lace look. I couldn't wear it to work, but what a fun look it is anyway!

    I also echo the sentiments above and appreciate that this post features some budget-friendly items.

    • August 22, 2017 / 1:18 pm

      Yessss Kelly! So much yes. Jewelry and accessories are an easy way for me to refresh an outfit so that I can fall in love with my clothing all over again.

      I have started a post on just that topic actually — 15-25 accessories that can freshen up a look. I don't know exactly when I'll be able to publish it, but it's in progress!

  4. maryeb
    August 22, 2017 / 12:22 pm

    Me too, Roxy. I also appreciate you taking the time to write such a helpful post. I love seeing how you style your outfits on Instagram and appreciate being able to read the thoughts that go into your styling ideas.
    You've offered such a wide variety of tips that, with the addition of a few new items, I can shop my closet and put together outfits in a new way.

    • August 22, 2017 / 1:19 pm

      That's so gratifying to hear maryeb, thank you! Piggy backing off of what I just replied to Kelly above, I am also working on the outline for a series on closet curating. I can't say exactly when it will be published, it may be a few months off to be honest. But it's in the pipeline.

  5. Shari
    August 24, 2017 / 9:57 am

    I have to say, more new items from JCrew and especially Madewell are filling my closet these days (and I find the JCrew shoes comfy if the heel is low enough). Has anyone seen the new anthro sept preshop? I added absolutely zero to my wishlist. I don't know how this is righting the sinking ship. Really awful in my opinion.

    • August 24, 2017 / 10:02 am

      I am writing a post about it as we speak! Will be up shortly.

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