A reader recently asked me, “I want sneakers that I can wear with dress pants.” Okay, so it wasn’t so much a question as a statement. I replied, “I can totally help you. I will write a blog post dedicated to the dressy sneaker.” First though, let me preface this post by saying that a dress shoe looks best with slacks and dress pants. That’s just a fact. But the dressy sneakers below are a Vanessa-approved cheat. The good news?! All these shoes also look amazeballs with chinos and jeans. You’re happy, I know.
Common Projects Original Achilles Sneaker
I love the off white color of this Common Projects Original Achilles Sneaker. It pairs well with light-colored jeans and tan to beige pants. It also looks great with pastels. I just don’t know how many of you will wear this fabulous pastel suit.
Wolverine 1000 Mile Original Sneaker
Cole Haan Original Grand Wingtip Derby
I am a big fan of this Cole Haan Original Grand Wingtip Derby. Pair this dressy sneaker with chinos, tweedy dress pants, like these Ted Baker London Padtron Dress Pants, and grey suits. This shoe is available at Nordstrom, Zappos, Macy’s, and Cole Haan.
Josef Seibel Tyler Wingtip
Like most of these dressy sneakers, these Josef Seibel Tyler Wingtips are unique. Pair these with jeans, chinos, and, you guessed it, dress pants. Notice how the more pointed toe dressy sneakers look best with true dress pants and suits. This sneaker is available at Nordstrom and Dillard’s.
Hush Puppies Expert Plain Toe Derby
This Hush Puppies Expert Plain Toe Derby has a more robust and rounded toe, so keep it for jeans, chinos, and more casual dress looks, like this grey suit, and these Ted Baker dress pants. This shoe is available at Nordstrom and Dillard’s.
Ecco ST1 Hybrid Plain Toe Derby
This Ecco ST1 Hybrid Plain Toe Derby is one of my favorite funky dressy sneakers. It goes great with chinos, tweedy dress pants, and this Boss suit. This sneaker is available at Nordstrom, Amazon, Zappos, Ecco, and Dillard’s.
Cole Haan ZeroGrand Stitch-lite Wingtip Oxford
Pair these Cole Haan ZeroGrand Stitch-lite Wingtip Oxfords with tan jeans or chinos as well as with textured dressy pieces, like this tech performance pant by Vince Camuto. This shoe is available at Nordstrom, Cole Haan, Neiman Marcus, and Macy’s.
Josef Seibel Tyler 09 Derby
This Josef Seibel Tyler 09 Derby is really more oxford than sneaker, but it’s still a hybrid. Pair it with jeans, chinos, and a tweed or cotton suit or dress pants. This shoe is available at Nordstrom and Dillard’s.
Gordon Rush Fletcher Buck Shoe
I know this Gordon Rush Fletcher Buck Shoe wouldn’t really be labeled as a sneaker, but it is just so comfortable that I had to add it to the list. It will shine with jeans and chinos, and work with a cotton or tweedy suit. This sneaker is available at Nordstrom and Zappos.
Santoni Doyle Sneaker
This Santoni Doyle Sneaker is the mothership of dressy sneakers. This sneaker actually does work with a suit. It is not a cheat. You can wear these dress sneakers proudly. They’re available at Nordstrom, Saks 5th Avenue, Neiman Marcus, and Zappos.
Santoni Doyle Plain Toe Derby Sneaker
Try this Santoni Doyle Plain Toe Derby Sneaker with a cotton or tweed suit or with dress pants and see how you feel. It definitely does a great job of connecting a sneaker sole to a dressy oxford. It is available at Nordstrom and Zappos.
J&M 1850 Martell Plain Toe Derby
This J&M 1850 Martell Plain Toe Derby is another dressy sneaker that can actually be worn with a unique suit, like this Topman burgundy look, or dress slacks. It is available at Nordstrom, Zappos, and Dillard’s.
Good Man Brand Legend Low Top Sneaker
Hush Puppies Heath Sneaker
I think I have a crush on these Hush Puppies Heath Sneakers. I really appreciate how they added a more unique sole to the usual leather sneaker. These will look best paired with jeans and more casual or trendy dress pieces. This sneaker is available at Nordstrom, Zappos, and Amazon.