Weekend Trip Essentials – Footwear Edition

You know the dilemma, you’re taking a long weekend trip and want to fit everything in a carry-on bag.

If you’re like me, you value options when it comes to your wardrobe and even more so, your shoes. You’re planning a fun weekend trip, hope to get a run in, and hope to go out for a nice dinner Saturday night.

Space is at a premium and you can only take two pair of shoes, the ones on your feet and one more in your bag. So, what do you pack?

  1. First things first, if you want to get that run in and offset some of the weekend indulgences you need a pair of running shoes. To add some versatility to your dress options, a running shoe that can be worn casually is your best bet. Go with something neutral that you can wear to lunch or walking around being a tourist. Stick to grey/black/blue so the shoe scan be worn with just about any color pallet. If you can, avoid packing your running shoes covered in reflective highlights or gaudy coloring that are a dead giveaway you’re sporting running shoes. You don’t want everyone know they need to sit at the other end of the table to avoid smelling your shoes.
  2. If the time of year falls between Memorial and Labor Day or you’re headed somewhere tropical, a leather pair of sandals is the way to go. Nothing says, “I’m relaxed, but still know how to present myself,” like a nice pair of sandals during the summer. A good rule of thumb is if they’re less than $30 or have a bottle opener on the bottom… you’re too old to wear those out on a date.

For those colder months of the year, a pair of leather chukka boots is a must for a weekend trip. A nice pair of casual boots can be worn with during any outside activity during the day or dressed up with a pair of dark jeans or chinos for dinner in the evening. Versatility is the key and boots provide just that!

If you’re flying, wearing your bulkiest or toughest-to-pack pair of shoes will free up some space in your bag. Perhaps you have a pair of shoes you really don’t want to smoosh in your carry-on, roll up your socks and stuff them in the toes of the shoes so they will hold their shape. This will keep your shoes looking nicer, longer, and keep you looking good all weekend long.

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