How to Wear Booties to Work

How to Wear Booties to Work One thing is certain, women are loving booties this fall.  Yesterday, while I was out, I spotted so many women embracing this trend that it took me no time to snap some shots of how they are wearing them.  I put all these photos together, that I took on the subway, the street and Penn Station while waiting for a train to New Jersey, in a quick little street style video that you can watch here.

I really enjoyed people watching and snapping these photos.  Seriously, if I could do this everyday I would.  Instead of getting lost in my phone, my Facebook feed or getting to another level of a stupid iPhone game, I had my eyes open to what was going on around me while using an objective eye to look at how everyone chooses to leave the house.

I had booties in mind because I knew I was working on this post on how to wear booties to work.  A lot of the looks in the video are more casual so the outfits below will give you some tips on how to wear booties in a more professional manner, from more corporate to business causal.

How to wear booties to work

Outfit #1

how to wear booties to work These red suede booties from Sole Society are like the bootie equivalent of adding a pair of bold colored pumps to a look.  They work particularly well with pants because colorful boots can be challenging to wear with skirts and dresses.  Unless you want to keep your legs bare or wear nude stockings, finding the right opaque tights to wear with red booties can be tricky.

In the look above, I particularly love the way these booties add some sharp contrast to a pretty basic look consisting of a pair of wide leg flannel pants in grey from Theory, a jewel neck top from Tuxe Bodywear and cropped blazer from Hugo Boss.  To complete the modern look, I added this statement pendant from Nest and bangle from Alexis Bittar.

Outfit #2

How to Wear booties to work I love dresses with booties.  As you saw in the video, a lot of women are wearing booties with opaque tights and, usually, the booties and tights are in the same color to create a long, lean, monochromatic look.  If black isn’t your color, you can do the same with chocolate brown and grey.  In cases where tall boots seem too heavy, try booties instead.

In the outfit above, this basic grey dress from Boden looks fun, yet still professional, with these heeled booties from Karen Scott and black opaque tights from Merona.  To finish the look, I filled in the neckline with this statement necklace from Jules Smith.

Outfit #3

How to wear booties to work For business casual, a pair of chelsea boots, like these from Modcloth, can really work well with skinny trousers, like this pair from J. Crew.  To make this look work, the pants will sit over the booties while being short enough that there is no pooling of the hem of the pants where they meet the boots.  You want a clean, slim look.  It’s perfectly find if a little ankle shows when wearing an outfit like this.

For such a lean look on the bottom, this easier tunic sweater from Reiss creates a balanced proportion and the look is finished professionally with a printed scarf, Kendra Scott drop earrings and Bauble Bar stacked bracelets.

Outfit #4

How to wear booties to work It’s completely up to you whether or not you want to keep your legs bare when wearing booties with skirts and dresses.  If you like the look above with these burgundy booties from Lord & Taylor, grey wrap skirt from Miss Selfridge, basic white button down and simple gold pendant, but want to cover your legs, you can add tights.  Burgundy may be more more colorful than you are used to, but the color is dark enough that you can add black tights and still look great.

Outfit #5

How to Wear booties to work This last look is another popular way that women have been wearing booties this fall, as seen in the video.  Taking flat booties, like this pair from Reiss, and tucking slim leggings or skinny pants into them creates this lean, almost elfin-like look that is really comfortable while being really stylish.  In this case, unlike a chelsea boot, that sits closer to the ankle, a wider shaft opening allows the pants to be tucked in while still leaving some room.

In this outfit, I created a totally monochromatic column look, that isn’t overly accessorized, using these pants from Piazza Sempione and turtleneck from Theory.  Over the column, I added this relaxed cardigan jacket from Zara and finished the look with black stud earrings from Marc by Marc Jacobs.

However you plan on wearing booties this fall, enjoy them casually and professionally.  I hope these tips, the video and outfit suggestions help.

Shop for Booties for Work

Check out these additional booties you can wear to work.

  • Susan Ashworth

    I LOVE the video. More, more! I like to see what real women are doing, and your commentary puts it all in context.

  • Renee Augustine Mathis

    The video was a treat! Thanks for the real-world examples 🙂

    • Thanks Renee! I am glad you enjoyed it. I got those photos in under an hour which proves how popular booties are. I will definitely try to take more street photos more often. I really do enjoy it.

  • Brooke Hamilton

    Great post, as I’m wearing booties to work today! I have like black wedge booties with laces up the middle.

  • stacie

    I loved the video!!! I’d like to wear my polka dot hose (classy) with my black booties and a grey dress like you have in your post…do you think it would look alright? Thanks!

  • Lee4

    Thanks for doing this–very helpful! I wear lots of ankle pants with flats or sandals in warmer weather & have wondered about trying them with ankle boots. Think I’ll do some experimenting this weekend.