Simplifying Your Workwear One Dress at a Time

by Rachel Yeomans | July 20th, 2011   

Workwear can be quite complicated. You have your slacks, your blouse, your camisole under the blouse, the appropriate shoes for the length of the pants, the debate on hosiery, should there be a jacket or no jacket…and we didn’t even get to accessories and makeup. Yes, there are times you need to spend some time really putting an outfit together. Other times the outfit can really work for you.

Picture 42 Simplifying Your Workwear One Dress at a Time

Dear readers, this is an ode to the dress. The next time you are standing in front of your closet wondering how to fit your outfit puzzle pieces together, shift direction to the shift dress. Granted there are some basics you should know when wearing the dress to the office (nothing’s ever that easy now is it?). Plus if you are just beginning to build your dress collection, keep these rules in mind while shopping for said dresses.

  • Length
    • Your dress should be no more than one inch above the knee. Ideally it should be right at the knee.
    • A good gauge on appropriate length is if you sit down in the dress, the hemline should not reach up your thigh; it should stop just above the knee.
  • Neckline
    • Personally my favorite dress neckline is the boatneck. It’s high enough to be work-appropriate, but it also gives the illusion of good posture and broad shoulders (ideal for petite frames).
    • You can wear v-necks and scoop-necks of course, but if any decolletage peeks though or if you have to be wary of bending over to pick anything up, either wear a slip underneath or leave the frock at home for weekend-wear.
  • Hosiery
    • Some offices strictly forbid bare legs at the office. So when wearing that dress to work, consult your dress code or HR department to see if this would apply at your place of work.
  • Sleeves
    • It is always easiest to wear a dress to work that has sleeves versus one that does not.
    • Yes, short sleeves on a dress can at times not be flattering on the arm area. When thinking of wearing a short-sleeved dress, wear one that has a looser-fitting fabric such as jersey or smooth cotton with an open-bell sleeve (NOTE: This would be appropriate for casual Friday and maybe not for the regular workday depending on your office dress code).
    • Long-sleeves (same rule as a blouse) should reach just past the wrist.
    • 3/4-length is always a flattering sleeve length. This length can also be fun to layer with a short-sleeved blazer to add a fashionable edge to your outfit.

Now for the sleeveless dress. There are a few additional options of wearing a sleeveless dress to the office than those listed above. Yes, it is the summer and that sleeveless dress is probably the first one on your mind when you’re getting ready to work in the morning. If your office allows you to bare arms, then you are in luck! However, although sleeveless may be the most comfortable for you, your boss may err on the side of professionalism versus comfort. If that is the case, here are a few ways you can still work the sleeveless shift.

Picture 52 Simplifying Your Workwear One Dress at a Time

  • Wear a long- or 3/4-length sleeved blouse underneath your sleeveless dress
  • Layer on top of the dress with a blazer or cardigan. And if you are worried about looking boxy under the layers, add a belt over your top layer to maintain the hourglass shape of the outfit.

With these basics in mind, now let’s talk about add-ons. We already went through the option of adding cardigans and blazers. But we can’t forget about accessories!

Necklaces always add a bit of something to whatever outfit you are wearing. Yet the same rules apply to your dress neckline as they do for your blouses. Your necklace should not fight with your neckline. If you are wearing beads and they are covering your neckline, you may want to opt for strands that hit right at your collarbone. If you’re wearing long strands, opt for a higher-neck for your dress.

As for bracelets, earrings, rings, etc., keep your best judgement in mind. Wear one statement piece. If it’s a necklace, then wear studs and a simple ring. If it’s a statement ring, don’t wear a bracelet. Long earrings? May want to skip the necklace.

Picture 62 Simplifying Your Workwear One Dress at a TimeJust as your closet is organized by work attire versus play attire, now it’s time to merge some of those items into the middle area of your closet (think of all those black dresses you can work with!). Still perfectly fun and frivolous enough for a night out, but also completely manageable for closing a business deal. And just think how much easier it’ll be going straight from that business deal to a celebratory cocktail after!


Just found this post today - but it's a great breakdown of how to work dresses into your professional wardrobe! I am a huge dress fan and will put these tips to work.


Rachel, thanks for this in-depth post on office attire. I agree with you; getting ready in a work-appropriate outfit can be so difficult some days! I've taken to laying out my outfits the night before so I'm thinking (somewhat) clearly and I'm not rushing around. I'm lucky to be working in an office where everyone dresses casually, but I still like to be careful and thoughtful when picking out my outfits. You can usually find me in some form of this outfit: darkest blue wash of Banana Republic's ultimate skinny jeans (hit at the ankle; great for flats!), an embellished tee or tank, and a cardigan. I'm thankful that the dress code here is relaxed, but your post is going to be bookmarked for those days when the dress code may be a little more corporate. and a little less San Francisco start-up. ;)

theworkwardrobe moderator

@annedreshfield Anne thank you for the lovely compliment! I'm so glad you found the post informative, and I definitely do hope it comes in handy on those more corporate-y days! ;)