­Each season, we ask a few Timberland employees pick their favorite footwear styles to wear in a “Staff Picks” photoshoot. This season, we are excited to introduce not one but two Katies to share their picks and styling tips.

Model: Katie Guest – Accessories Merchant, Footwear 

Katie is a Merchant at Timberland, and has plenty of credibility when it comes to style. “I love keeping up with the trends and looking to future opportunities that we could incorporate into the line.”

Katie picked the Kellis Wedge Chelsea Boots for their style and versatility. “They are super comfortable since they have the wedge and they go with EVERYTHING.” Katie switches up the styling of this boot as the seasons change. “In the cooler days of the summer I like wearing them with a floral dress, giving it almost a grunge vibe since the boots are more ruggedly feminine. I am also excited to wear these with a thick grey boot sock with black jeans and a nice leather jacket for the fall.” 

Model: Katie O’Connor – Associate Brand Manager

In addition to being Timberland’s Associate Brand Manager, Katie O’Connor is also a studio dance teacher. This informed her choice of the FlyRoam. She was initially drawn to their pastel pink color, perfect for the fall, and was won over by the comfort of the Aerocore technology. “They are great for throwing on when I’m on my way to the studio or heading out to meet friends for lunch.”

Katie likes that she can also work these shoes into her office wardrobe. “Pair them with jeans and a leather jacket and if you have a casual workplace like we do at Timberland you’re good to go.”

Can’t get enough of our staff picks? Head over to this post to check out some of our men’s top styles for the season.