Let's start with what you'll need to pack:
Undergarments- You can figure that out. But while we're talking about it, I recommend Calvin Klein. If you're going to a log cabin where you are likely to see a bear, bring an extra pair of underpants.
Tops- The general rule I follow is three shirts, one sweater. If you're headed for a warmer place, I recommend two tanks and one t-shirt. If you're headed upstate, it's better to wear long sleeves and button-ups. Keep it simple here- solid colors and simple patterns. Never bring a graphic tee. In fact, never wear a graphic tee. For virtually any style and a wide price-range, Bluefly is a good bet.
Sweaters- Again, simpler is better- a cardigan or simple pullover. This is my favorite sweater in the world (currently on sale) so buy one in every color.
Pants- I usually bring two pairs of pants- one pair of jeans and another of chinos/cords/leggings. For jeans, I like Joe's or Citizens of Humanity. As far as trousers, J.Crew usually has a decent selection.
Dresses- Choosing the right dress is hard because you should really only bring one. When choosing the right day-to-night dress, keep it simple so you can dress it up or down. Even an LBD will do if you pair it with a light cardigan and flats during the day, and heels at night. I cannot tell you where to buy a little black dress because there are too many options and it's so personal but ShopBop has a good selection.
Jackets- Obviously it's good to bring a jacket no matter where you're going. If you're going someplace tropical or rainy, bring a rain jacket (duh). If you're going someplace chilly, dress accordingly. Orvis is pretty great no matter what you're looking for.
Shoes- Packing shoes is always the hardest for me. It completely depends on what you're doing but you can probably figure it out yourself. If you're going to the beach, bring flip flops. If you're going to walk a lot, bring sneakers. If you're going to a night club, bring heels. If you're just hanging out, I live in Bass loafers and J.Crew flats.
Toiletries- That's on you. Don't forget a toothbrush and deodorant. And for what it's worth, this Kiehl's face wash is amazing.
Make-up- My best friend has a makeup bag with about 30 things that she never uses in it. My make-up bag has about 10 things in it, all of which I use. Especially when you're on a vacation, you're likely to not use a ton of makeup so reel it in and bring only the essentials. For general reference, this is what I use:
- Foundation: Clinique is perfect for sensitive skin. I recommend the powder over the liquid if you're prone to oiliness.
- Blush: Lancome is light and very natural looking.
- Eyebrow Pencil: I had never used one until recently but I was quickly convinced of their benefits. I use TARTE.
- Eyeliner: YSL is my go-to. This stuff will look amazing even after a 12 hour day.
- Eye Shadow: I recommend investing in a palette with a lot of different colors so you can play with shading/contouring or just mix it up. I use Too Faced.
- Mascara: I have no eyelashes so mascara is important. I recently switched to Dior and it changed my life. This sh-t is no joke.
- Lips: I don't like a bunch of stuff all over my lips so I use Burt's Bees. Exclusively. And religiously.
Luggage- Finding the perfect weekender is a very religious personal experience, but I have a Longchamp that I bring with me everywhere. The Longchamp bag is a bit overdone but I really like the weekender because it's expandable and has a ton of space. If you're not as poor as me, this is lovely.
So pack a bag and go someplace beautiful.
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