
It’s the perfect time of year to take advantage of warmer evenings and grab a table outside. Spring nights hit that sweet spot: comfortable, unhurried, and made for lingering. And if your date is anything like mine, she’ll happily choose the patio and settle in for a long dinner.
For May, I lean into lighter tones with a confident pop of color (navy is doing a lot of work right now). Stay smart with layers. A lightweight jacket or sport coat goes a long way if the temperature dips, but elevate the whole look with strong loafers and a serious watch. And don’t forget your sunglasses. The sun isn’t setting until well after 8 PM.
Here’s how I like to do it:

From top left:
1. Sid Mashburn Navy Spread Collar Dress Shirt: I like mixing in a darker dress shirt every now and then, and this is a great opportunity (lighter pants, lighter jacket). You’ll get more wear out of this than you think.
2. Peter Millar Tempest Sunglasses: Don’t sleep on PM sunglasses. They are good, and typically about $100 less than other name-brand alternatives.
3. Ralph Lauren Seersucker Coach’s Jacket: I am a big fan of solid seersucker, and this jacket is a smart way to add a ‘coach’s jacket’ layer without dressing the outfit down.
4. Jacob Hill Caiman Matte Belt: I mean, it doesn’t get any better.
5. Faherty Light Blue 5-Pockets: It’s not light denim, but a garment dyed light blue. Really smart look. Make sure they are tailored well: little to no break.
6. Ferragamo Grandioso Loafers: A REALLY cool pair of loafers. Somewhat fashion-forward vs. what we typically talk about here, but worth it.
7. Rolex GMT Master: Bring out the big guns.
8. Stevie Wonder #1s: The Vibe…you forget how deep his catalog is.
What did I miss?