It might only be Wednesday right now, but my mind’s already thinking ahead to the weekend — I’m hitting the road for a family wedding in the lovely and historic city of Charleston, South Carolina (one of the home bases of my friends over at creative lifestyle site Brothers & Craft, in fact). And I’ve also been brainstorming how to pack in style while getting from fast-paced NYC to the decidedly more laidback Southern locale. Traveling and looking good is definitely something that should be top of mind for all of us as we hit the road the rest of this summer, too. Sharp travel accessories are one thing to elevate your overall game — but what do you wear while traveling and once you get there? Here’s a look at what I’m packing, and what you (maybe? possibly?) should throw in your bag, too. (Editor’s note: Unless you’re a real jetsetter, let’s assume you’re just packing for a long weekend away in a temperate climate – if it’s hotter or colder than that, layers could be added or subtracted). 

The Shirt: A Go-Anywhere Oxford Cloth Buttondown [+ Slim, casual T-shirts & polos]

Although that shirt seen above is sold out online (and it’s easy to see why), it’s the perfect stand-in for the type of shirt that would be perfect to wear when traveling — and to have once you get where you’re going. On the cheaper side of things, Old Navy offers up a version at a pricepoint that could allow you to get one in both white and blue. The classic Oxford cloth button-down is the ideal mix of casual-meets-crisp style; it can be paired with a lightweight spring or summer jacket or a blazer in dressier situations, and it works with chinos, stylish shorts or denim (as long as the fit is trim and the shirt doesn’t hang too low when untucked). On the more casual side of things, a polo or two also wouldn’t hurt — this year’s Michael Bastian x Uniqlo polos are affordably priced and feature a wide spread of colors and patterns. On the even more toned-down side of things, slim pocket tees are your friend for casual travel style — in a slim fit, the right tee can even be worn under a blazer.

The Pants: Slim chinos or dark denim [+ laidback shorts]

The slim khaki chino is an all-American classic that’s been freshened up as of late and can be worn just about any way you please (for at least five variations, see an Effortless Gent piece I penned last fall). Dark denim is every bit as versatile, too — either can go with pocket tees or polos, plus that trusty Oxford cloth buttondown shirt. The same goes for matching with different types of footwear, too (more on that below). And assuming you’re heading somewhere slightly warmer than where you are now, tailored shorts in a neutral color are a good pick — perhaps these Club Monaco shorts might do the trick, in fact. If you want something with some stretch and mobility, J. Crew Factory’s Stadium Shorts would be a wise wardrobe addition.

The Shoes: Crisp white or navy sneakers and brown leather loafers

White sneakers, especially in the world of men’s style nowadays, can be worn with just about anything — even a suit if you play your cards right. If you reach for a pair with a slim silhouette, like the GREATS Wilson, the styling potential is ready for just about any situation — short of a black tie dinner. Navy runner-style sneakers are an equally unique option that combine retro cool and modern flair as well. If the occasion calls for a dressier pair of footwear, a pair of classic leather loafers is virtually foolproof; functional and cooling with rolled chinos in hotter weather while still looking sharp. Rugged-yet-refined brown leather desert boots (like the Florsheim Jet Chukka) also strike the right note — and if you had room for just one other pair of shoes on your trip besides sneakers, they would be the best pickup.

The Watch: Stainless steel dive watch (Or your favorite, versatile timepiece)

When it comes down to it, space packing for a trip is limited, no matter how great your weekender bag might be. Packing one watch to meet a variety of situations is one way to free up some of space for souvenirs or another T-shirt or two. There are lots of options out there that fill the under-$100 price point and pack versatility into one package, and in a situation where you might have two pairs of shoes to mix and match with shorts, chinos and denim, ditching a leather strap (which would require coordination with your shoes and belt) is an easy fix. An interchangeable nylon-strap watch could easily stand in if the trip leans more casual (and you don’t mind coordinating with a blue dial).

The Jackets: A cotton knit jacket and a classic navy blazer

While the Grayers Russel Jacket seen in the photo at left is down to just Large and Extra-Large sizes, Old Navy can be counted on here to offer up an equally sporty and equally stylish jacket (made from cotton).  In the right fit and with the right staples (like a chambray shirt), an outfit very similar to the one on the left could be worn to work and then right onto the plane. Likewise, an unstructured navy blazer fits the bill perfectly if the occasion calls for something more polished. In a more wrinkle-resistant and lighter fabric, that same blazer could  be worn from the office onto  the plane, too.

The Rest: A reversible belt, versatile socks and a sharp swimsuit

Trying to coordinate different pairs of shoes together with varying types of bottoms is another hurdle that requires some packing expertise. The easy way out of that is a simple reversible belt — not always the highest-quality things on the market, to be sure, but effective nonetheless. That way, you solve that pesky space issue and pack (or most likely, wear) just one belt throughout the trip.  If space allows, a casual webbed belt could be a nice change of pace. Patterned socks are lots of fun, to be sure, but picking up a couple pairs in neutral colors — like grey, charcoal or navy — would work best for maximum versatility. And reaching for a swim suit with a slimmer cut, like any of the options from this site’s recent swimwear roundup helps you look good while hitting the water  (if that’s in the itinerary, that is).

So you’ve got some ideas from the above — what’s on your go-to list when packing? What would you add or omit from this packing suggestion? Give me a shout on Twitter!