Friends, I’ve got an opinion on everything sartorial.   I seem to filter my experiences through the prism of fashion.  Which is why when my clients ask me about what to wear on a first date, I share my insight.  And because it’s been a minute since I’ve addressed my male readers, this post is dedicated to the dandies.

The first thing to realize is that it’s all about the shoes, hence the title.  I liken the first date to an interview–you want to make a good first impression.  One of my favorite brands is To Boot New York, because the brand is rooted in classic designs with a fun pop of color or detail as an update.

to boot new york brent boot

This chelsea boot can be worn without any hint of the elastic gore in the vibrant blue showing.    Why not disarm her (or him) with the surprise to break the ice?  Since wardrobe is a form of expression, it’s a great entry to share something  about yourself!

first date cole haan camello chambray shoeFor a more traditional look, try this Cole Haan wingtip.  I love how it’s got a hint of color at the heel, and if you’re wanting a more straightforward look you can change out the laces.  Continuing with potential ice breakers, why not coordinate your socks with the shoelaces, or pick out a fun plaid that peeks out when you’re sitting.

Finally, for the more casual dresser (please note my strong suggestion that a sneaker be more of a second date option, unless the date is at a very relaxed setting), I love a sneaker with a polished twist.

first date converse star playerConverse, in collaboration with menswear designer John Varvatos has become a staple in my clients’ wardrobe.  These kicks paired with a v-neck and khakis, would be a great cofee date outfit…

No matter your first date sartorial choices, when you dress with confidence and joy it will show!

Need more first date wardrobe suggestions?  Book an appointment with Miramar, Personal Fashion Stylist at