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I’m going out of town soon, and while I eventually may be more concerned about how I look without clothes, figuring out what to pack is always a challenge—particularly when you're leaving someplace frigid for someplace with (hopefully) more temperate weather. And of course there's the issue of designing an outfit around easy-to-remove footwear for the flights. And making sure sure everything fits into a carry-on.
The key, of course, is to have everything work together. For me, that means going classic—a lot of neutrals, with color and personal style provided by accessories—because if you’re going all Lady Gaga, you better make sure you have the entourage to carry your luggage for you.
A vacation is not the time to debut anything you haven't worn before. Maybe you'll decide it's too girly for you, or it looks too dressy in a casual environment, or the waistband is cutting. You'll look and feel uncomfortable and will be thinking more about your clothes than the experience. Go with the tried-and-true.
There won’t be a lot of snow where I’m going (or so I hope), so a pair of wide-legged black pants will be my fancy-dinner outfit and can work for day as well. A black scoopneck sweater can go with jeans or the pants and can be dressed up with a giant necklace. If it weren’t so fracking freezing here, I could probably get away with this season’s boyfriend blazer as outerwear, over a sweater and a scarf, and then over a T-shirt on warmer days, but I'll probably need my winter coat just to get to and from the airport, so a cardigan in gray or navy blue will probably be a better choice to cram into my carry-on. A long-sleeved tee—such as the currently popular French-style striped sailor tee—could be worn by itself or with that cardigan. If I’ve got room I'll add a black skirt and tuck in a few pairs of colored tights for variation. Shoes? Simple: a pair of flat boots that can do triple duty: I can tuck my jeans into them, wear them with the black pants, and with the skirt and tights. In warmer climes I'd trade my winter coat for a trench and add a pair of flats.
By the way, there's a reason the pashmina scarf is so ubiquitous: it's brilliant. It can keep you warm on the plane in place of a grotty blanket, bring color to one of these neutral outfits, or provide a dry seat on a hike.