What to Pack for a Trip South at Thanksgiving

The countdown to T-Day—Turkey Day, that is—has begun, and while some of you have started dreaming (maybe it’s a nightmare? LOL) about entertaining family and friends and cooking up a storm, others might be getting away from it all by heading south.

Deciding what to pack for a vacation is always a fashion puzzle and even more challenging if it’s cold outside and you are headed somewhere much warmer, like Florida or the Caribbean.

To help you pack, here are three outfit ideas that work in warmer climates.

Black and White Sleeveless Top Black Pants


1.  Black Pants + Sleeveless Top + Sandals

LBPs—or little black pants—are a wardrobe workhorse. They’re more dressy than jeans but more relaxed than a dress or skirt; they’re perfect for travel because they are super comfy, and you can dress them up or down for maximum utility. These are the four-season cropped pants by J.Crew that work in any climate!

I’ve paired them with this handkerchief hem top. This piece floats elegantly away from the body, keeping you cool, and is easy-care machine washable. Finally, I’ve added metallic sandals and a metallic bag to dress up this look.

day dress for florida


2. Day Dress

It’s always handy to take along a cute day dress for shopping or going for lunch; a nautical style like this is always in style. I like the 3/4 length sleeves, which give you some coverage but always look youthful. A little sundress like this is usually on the short side, so flats look great.



3.  Shorts + T-Shirt+ Denim Jacket + Espadrilles

This last outfit is perfect for a fun vacation when you’re on the go all day and need something cute, comfy, and casual to see you through. Start with a pair of shorts.

These are called ‘urban’ shorts, perfect for sightseeing. Add a go-with-everything gray t-shirt, classic denim jacket, and espadrilles, and you’ve got a classic and classy outfit.

Bonus: the pieces will mix and match well with many other things, making them ideal for a travel capsule wardrobe. This is an easy, relaxed outfit for hanging around a beach town.

Blue Maxi Dress


2.  Maxi Dress + Sandals + Statement Earrings

If you are going someplace beachy and warm, there is nothing prettier than an easy, breezy maxi dress. This blue and white ruffled maxi has a lovely, boho-lite vibe. I’ve kept it classy with pretty gold sandals and long gold earrings that play up the appeal of the off-the-shoulder style.

Are you planning south sometime during the next few months or during spring break? What’s your go-to packing strategy?

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8 thoughts on “What to Pack for a Trip South at Thanksgiving

  1. UGH. Capri’s. Very few women in Naples, FL, correctly style Capri pants or leggings. Capri’s with a poorly fitted tee-shirt and sensible brown sandals seems to be the norm. All women would look better in slacks, ankle-length, or longer. Every winter, I see the women coming down to Naples with their Capri’s. Such a stereotype for women over 40. Time to change it up!

    1. I’m more of a fan of ankle-cropped pants myself and wear them all the time in Florida. I think they are more flattering than shorter capris, but many of my readers love their capris. Capris can look cute if you pay attention to your footwear and top, as you suggest.

  2. Thank you, Deborah :)
    I live in Florida and am always looking for ideas for warm weather. Most blog posts this time of year are about sweaters and boots, so it’s great to see a sunny Florida suitable post.

  3. Deb, what a great post! I hardly ever get time to look at blogs! I love your suggestions and envy the thought of warm weather! Can you believe the holidays are right around the corner???!!! XO

  4. If you are coming to the Caribbean, make sure the maxi dress is light and floaty. Capri leggings would be a better choice than full length. I live in Barbados. I do not keep anything there with a sleeve longer than cap length. Lightweight tops and floaty dresses are best. I never wear pants here, but the locals do. It might be what you get acclimatized to, too.

    The other place I hung out was Phoenix. At Thanksgiving, you will want a lightweight sweater, a vest to go over it for the mornings, and a wrap for the evenings. It gets cool in the desert at night.

  5. In the southern part of the US (the Carolinas, etc.), even though it is not cold, it is excellent in the fall, and even when it is warm, we don’t wear super-summery clothing like white linen and sundresses in November. We still wear sweaters; they are just cotton and lighter weight. It is not perpetual summer in the South.

  6. How far south are you going – Mexico? It won’t be warm enough here in south Texas for shorts or sleeveless tops without a jacket by Thanksgiving. Cute outfits, though!

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