Sunglasses in. Watch on. Shoes set. Bag packed. The summer associate's starting kit, built to carry you from 8am to whenever they finally let you leave.
There's a specific kind of nervous that comes with a first day. Not the bad kind — the kind that means something is actually happening. You've earned this desk, this badge, this terrible coffee from the office kitchen. The clothes question should be the easiest part of the morning. It usually isn't. We're fixing that.
Four pieces. Each one earns its place at a specific hour. None of them will break your first paycheck. All of them will be asked about before the summer is over.
You leave your place at eight. The city has a particular feeling at that hour — still yours, before you belong to anyone's schedule or conference room. This is the moment for the Wayfarer. At $154 they're the least expensive piece in this kit and probably the highest-return. Classic black frame, G-15 lens, the exact silhouette that's been photographed on people who looked like they knew what they were doing since 1968. Put them on and walk like you've already done this.
The all-hands starts at 9:30. Fifteen people in a glass conference room deciding in the first thirty seconds whether you're someone to pay attention to. You'll want to know what time it is without pulling out your phone. A phone says you're waiting for something else to happen. A watch says you're present.
"A phone says you're waiting for something else to happen. A watch says you're present."
The Orient Bambino Version 4 runs at $130. Mechanical automatic movement, domed crystal, a clean white dial with Roman numerals that reads from across a table. It looks like it costs $500. When someone glances at it during a handshake — and someone will — it registers as a person who pays attention to details. That's exactly the impression you need in week one.
Your manager mentions lunch like it's a short walk. It's five blocks. In the wrong shoes, five blocks in a business district is a negotiation. In the Cole Haan ØriginalGrand Wingtip, it's just a walk. Full Oxford silhouette, genuine craftsmanship up top — and a cushioned Grand.OS sole borrowed from Cole Haan's athletic line running underneath where no one can see it. You will stand on these shoes for eleven hours today. Your feet will feel fine. On a first day, that matters more than almost anything else on this list.
They hand you a folder at 2:00. An orientation packet at 3:30. A compliance document at 4:15. A notebook at 4:45. By 5:30 you are carrying significantly more out of that building than you walked in with. The Aer Work Pack 2 is $185. Holds a 16-inch laptop, has enough internal organization to feel like a system rather than just a bag, and comes in a clean matte black that sits against any outfit without asking for attention. You wore it this morning looking like you had somewhere to be. You're wearing it now because you did.
You'll be nervous on the first day regardless. Everyone is. But you won't be underdressed. And on a day where most things are out of your control, showing up prepared is the one move that's entirely yours.
Virgil built this shoe to go everywhere. We tested that theory thoroughly.
Virgil built this shoe to go everywhere. That wasn't an accident. The Out Of Office doesn't have the hype cycle of a Jordan, doesn't need a bot or a resale market to validate it. It's a clean, considered sneaker that works with literally everything you own — which is exactly why it's the Chess side's most recommended shoe right now.
White leather upper with enough structure to look deliberate. A chunky sole that reads street without tipping into costume. Those quote marks that signal you know what you're wearing without making it a whole conversation. It's a sneaker that's in on the joke without winking too hard.
"Wear things that work on multiple levels. The fit should read club without announcing club."
Where you can actually wear them: with a Chrome Hearts ring and a black silk shirt to the kind of club that doesn't have a sign on the door. With wide-leg black trousers and a simple tee to a creative industry first meeting. With a track jacket and cargos to everywhere in between.
The Chrome Hearts cross ring is the other move. Real silver, real weight, unmistakable. People who know, know. People who don't will just think you have taste — which is also the correct outcome. Stack it with a plain band or wear it alone. Either way, it's the detail that finishes the fit.
This is the Chess philosophy. You know when it's working when people ask what you're wearing without being able to explain exactly why they noticed.