For both of my two-day/three-night trips—in which I needed to look “put-together but cool”—I brought: one pair of cargo pants (worn on the flight), one pair of jeans or khakis, two everyday tops (groovy tees from Eckhaus Latta that are elevated but unfussy), one nicer top that in a pinch can dress up the pants for going out in the evening, an extra top to wear on the return flight, one nice dress for dinner, a small bag that can be worn daytime and nighttime, a pair of sneakers or whatever I wear on the plane, a pair of nice flats, a pair of heels, and a jacket (plus underwear, pajamas, etc). Together, they constituted two daytime outfits and two nighttime outfits with different degrees of “dressy-ness,” plus travel outfits. (On previous trips in which I needed to be dressier the list has looked more or less the same, just with skirts instead of pants, and perhaps one extra dress.) Everything easily fit in my carry-on bag with room to spare.

The pieces that make up your daily outfits will likely differ, but the math is simple. The bottom line is that you should pack in an exacting and ruthless manner (though I must add, I’m a fan of throwing in a piece on a whim! I think especially if you are a person who dresses according to mood, it’s helpful to know you have something in your suitcase whose entire purpose is to “bring joy.”)

If you’re taking a trip that’s over three nights—let’s say five to seven nights, that’s when you can let a little bit of the fantasy seep in because, well, a bigger suitcase has room for dreams. I still recommend you pack in “outfits,” but now you can start adding alternatives as well, like an extra top for a pair of pants you want to wear or vice versa, and this is absolutely the time to pack that one suit you love and you’ve never worn before but are sure you’ll wear it this time.

Now, when it comes to shoes, just pack however many you think works. I can only manage to keep the number manageable when it’s a quick trip—for a longer trip I feel like I need at least five? I admit one of the pairs will often come back unworn, but better safe than sorry, I think! Or should I say better chic than saving money on an overweight suitcase!