Look the part(y).
How to dress when attending an outdoor event—from casual to formal.
If you’re familiar with the movie Wedding Crashers, Vince Vaughan’s character initially refused an invite to the Cleary family compound because he had “nothing to wear.” And, upon arriving, what was he given for the outdoor activities that were planned? Madras pants. While it wasn’t a look he was used to, he pulled it off. You have this same style opportunity when invited to a warm-weather outdoor event—and it’s one you shouldn’t pass up.
Keep in mind, there are degrees of formality when it comes to these kinds of events. It’s best to acquaint yourself with the looks that go with each before you reach for a pair of madras pants and think you’re covered.
The boss’s BBQ.
First of all, even though these are generally casual affairs, unless your boss lives in the Hamptons and it’s expected that you’ll be hitting the beach, put the idea of wearing flip-flops or sandals out of your mind. And along the same lines, let someone else wear the Hawaiian shirt or, even worse, the dress shirt and surf trunks (yes, we’ve seen it).
So, after avoiding these pitfalls, decide on shorts or pants depending on how hot the day is going to be. You’ll possibly be on a deck or patio in the sun, so a white polo shirt, khaki shorts, and boat shoes or white sneakers (no, not the ones you wore playing lacrosse in the backyard) is a good place to start. Add color by changing out the khaki shorts for a yellow or light blue pair. Or maybe you find a summery sport shirt with an interesting pattern and color combination to pair with your khakis.
If it’s expected that you stay into the evening, think about bringing a navy blazer along or a v-neck sweater. And remember, even though you’re there to have fun, it is still the boss’s house after all and not Spring Break in Cancun. So dressing appropriately is a must.
The garden party.
When people hear “garden party” immediately images of seersucker jackets and creased khakis come to mind. And they’re not wrong. It’s probably the most formal kind of outdoor affair you’ll be invited to, other than a wedding. But just because you’ll be enjoying wine and hors d’oeuvres instead of beer and BBQ, that shouldn’t stop you from putting together an interesting look.
Unless a certain dress code is specified, begin by figuring out where you want to add some flair. Think about adding color or pattern to your look, instead of doing the standard khakis, white dress shirt, and seersucker blazer. Consider those madras pants Vince Vaughan wore. Then pair them with a yellow or pink polo shirt and a navy blazer—maybe an unstructured one, to keep it relaxed.
If madras isn’t your thing, how about a fun patterned sport coat? Or consider a brightly colored short-sleeve button-down with a solid sweater vest. Or a white polo with an argyle sweater vest.
For footwear, choose from loafers, bucks, or saddle bucks. This definitely isn’t the place for flip-flops or sandals. Those are fine when you’re weighing a white marlin on the dock, not when eating mini-crab cakes in the courtyard.
If you think about what the characters are wearing in movies like The Importance of Being Earnest or Midnight in the Garden of Good and Evil you know how formal the garden party can be. But a little bit of flair is always welcome.
The Kentucky Derby party.
OK, here’s where things get serious from a style standpoint. Because just like every horse in the field at Churchill Downs wants to win the race, every guy who attends a Kentucky Derby party wants to be the best dressed. It’s that rare occasion where the guys actually are encouraged to outshine the ladies and, like a horse in the race, it’s an opportunity that you shouldn’t let pass you by.
Perhaps it’s best to say that every style suggestion we made for the previous two events will be bumped up significantly here. That means colorful pants aren’t an option, they’re expected. Don’t shy away from lime green or pink or tangerine or yellow either. Have some with embroidered horses and jockeys on them? Even better. Pair them with a light blue gingham check shirt and you’re starting to get in the swing of things. For a jacket, a traditional navy blazer will work fine, although pairing tangerine trousers with a canary yellow jacket, or vice versa, ups the ante considerably. And, of course, accessories like colorful pocket squares are always encouraged.
A Kentucky Derby party is also a good time to break out the bow ties you’ve never quite gotten around to wearing. Or pick out a straight tie with a bold stripe that complements the solid colors you’re wearing. And, if you couldn’t find pants with embroidery, maybe this is where the tie with the embroidered horses comes in.
Shoes are a big part of this look too, so be sure to pick ones with as much visual interest as the rest of your clothes. The spectator shoe, an oxford or brogue that has two contrasting colors, is a popular choice. And even though the ladies have the market cornered on outrageous headwear, that doesn’t mean you shouldn’t top off your look with a nice hat. A straw hat or boater will do the trick. These guys get what’s of expected of them.
If these kinds of colorful looks seem to be far, far, outside your comfort zone don’t worry, you’re not alone. But fortune favors the bold. And if you feel you’re drawing too much attention, you can always divert unwanted gazes by pointing to the outlandish hats the ladies will be wearing. And if that fails, there will be plenty of Mint Juleps nearby.
Because these are warm weather events, you’re going to want to choose lightweight fabrics that breathe. Cotton and linen are great choices. Stick with them, because nothing brings the fun to a screeching halt quite like looking at yourself in the bathroom mirror and discovering that you’re sweating through your wool sport coat.
The reason for all this.
Events like these are special because they occur during that all-too-brief time of year when the weather warms, the days lengthen, and just being outside feels like a celebration. It’s the perfect time of year to cut loose a little, to break out of our navy suits, and have some fun. And while we can’t guarantee that, like Mr. Vaughan in Wedding Crashers, you’ll walk away with Isla Fisher on your arm because of it, but we’re pretty sure some favorable gazes will come your way.
- 67 2571