Packing for a weekend away is no simple task, especially when your work schedule dictates that you do it four days in advance (unfortunately being a gentleman doesn’t pay the bills but selling your soul to an exciting career in finance does).
This can also be a tricky, especially if you are mixing business and pleasure. The bootstrap gentleman, despite his modest upbringing, should be prepared for all manner of social interaction. It is important to remember that being best dressed isn’t about being the most original but being the individual who blends well with the crowd. You never know when the venue will switch from the hotel ballroom to the basement barroom so a top hat shouldn’t be the first thing on your list.
Remember when you are on a plane, train, bus, monorail, gondola-other people can see you, you shouldn’t be wearing sweatpants, shorts or sandals of any kind. When in doubt, exposed portions of your body are offensive to others. Traveling long distances, like most trips out of the house, used to be an event to look respectable for. This has not changed. Anyone caught dressed in hoodies or mesh shorts during transit should be forced to ride in the baggage compartment, they look like duffel bags anyway.
We digress.
Everything in your weekend bag should serve multiple purposes and go together (not match- think George Costanza’s father in a cabana set).
Bootstrap suggests:
-Oxford shirts- one white, one of a light color or pattern
-Jeans- no holes or frayed edges, you need to be able to wear these anywhere
-A blue blazer-it’s a classic that goes with everything. Wear it while you are traveling to hold your tickets, phone, wallet, keys, emergency life preserver etc.
-Chinos- a tailored pair that you can wear for casual or dress in khaki or grey
-Loafers- loafers are both formal and casual and they slip off easily for that nice TSA employee who will throw you in the mandatory pat-down holding pen for taking two minutes to unlace your ankle boots
-Sweater- solid color, v-neck or crew neck, no reindeer
These seven items fit easily into a weekender with some worn for traveling, and when mixed can create the proper attire for almost any occasion. If you want something more formal throw a simple tie and a pocket square in your bag and you are good to go.
And remember, if you are a real gentleman you should also think about how those clothes will look after a night on the floor and a walk home in the harsh light of day…happy travels.
