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Monday Outfit: Chic and Touristy

Jul 7, 2025

Normally, I would post a roundup of my weekend shopping and reading on Monday. But this weekend, I did no shopping (unless you can’t the hot dog buns) and I did almost no reading. Thus, we pivot.

Traveling usually involves sightseeing. Sightseeing can be difficult to dress for. You want to look nice in your photos, but you want to be dressed for the weather, and you need to be comfortable. So when I spotted an outfit that looked like it could get the job done, I set about recreating it immediately.

As mentioned, I found this look on Pinterest. It is impossible to source these photos most of the time, so if anyone knows who this one belongs to, please share. But how impossibly chic and easy and relaxed is this outfit? It’s so simple and easy to recreate, and yet, it feels a like a revelation.

The Dress // Breezy and light, this linen a-line shift is the perfect dressy, but not dressy, option for traveling. If it looks a little rumpled, it’s fine. It handles the weather like a champ. And you can wash it in a hotel sink and hang dry if you must.

Madewell has basically the exact dress — shift, sleeveless, pockets, line–but it is selling out in a rapid hurry, so get it while the getting is good. Old Navy has the same style, but not in white (petite, tall, plus). BR Factory has the same dress but in a v-neck. And if you don’t do linen, Athleta has a great white tank dress that will do the trick.

The Sweater // I wanted a cardigan for easy toss on and removal. I also thought a really chunky knit might add a nice textural element here. So this Alex Mill cardi was the pick. If you want something similar for less, Quince has this boxy fisherman’s cardigan.

Need help tying a sweater over your shoulders in a way that looks chic and not schlumpy? This Instagram video is just the trick.

The Hat // Yes, I know this hat is $125. I know it’s a little silly. But I bought the denim one and it’s fantastic, so I guess I’m a person who covers her second day hair with pricey ball caps now. Prefer something a bit cheaper and more fun? The logo hats at Clare V. are my favorite.

The Shoes // If you have never owned a pair of Birdie’s, I can’t say enough nice things about this brand. The shoes are so well made, so comfortable. They feel like walking on a cloud. If I had to do some walking, but not crazy walking, I would pick these sophisticated sandals for the comfort and style points. But let’s be real, for real sightseeing, I need low-profile sneakers.

The Accessories // This Strathberry bag is the stuff of dreams. If you want pretty, stylish, classic bags that cost less-than four-figures, this is your brand. Need something less expensive? This JW Pei bag is worth a look.

To finish the look, I chose these wide, textured hoops from Gorjana and these simple tortoise sunglasses from Madewell. Nothing earth-shattering, but both cool and easy to wear.

Styling // Someone recommended this Jones Road Lippie Stick, and I am obsessed. Just a hint of color. A moisturizing lip balm. Just toss it in your pocket (did I not mention the dress has pockets?), and go. Other than that, don’t forget the dry shampoo and the makeup setting spray.

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COMMENTS

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  1. linda says:

    Awesome finds! The only thing I have been adding to similar outfits is a pair of very lightweight silk shorts with an elastic waist. Short dresses are nice, but I have to be able to sit down in them without flashing anybody.

    https://poshmark.com/listing/Juliette-Jake-100-Silk-White-Blue-Print-Shorts-5cc4ceb6abe1ce64ec33aa06

    And I ignore the dry clean labels on these, wash them in a garment bag on cold and line dry.

  2. MARAMAR says:

    Regarding the chord hat: I avoid baseball caps in general because I think they make my head look small (and I already fret I am prone to the small-head/big-body issue). How does this sit on the head? Does it make it look smaller at all?

    I would love to wear a cap but dont want to look like whatever the opposite of a pinhead is! (Maybe a triangle? An iceberg? An eggplant? Unsure)

    • Belle says:

      That’s one of the “magical” things about this hat. It’s actually cut to fit your head as opposed to looking like it’s too big for your head. So you may find it looks better because it’s slimmer fitting.

  3. irmck says:

    THANK YOU for the sneaker recs. My husband owns a walking tour company, so his idea of a “normal” amount of walking on vacation is very much not normal. Cute shoes won’t cut it, I need very supportive sneakers. It’s nice when they are also cute.

  4. Jody says:

    I really want to try the Jones Road products! Have you tried any other? Like the Miracle Balm?

  5. Chelsea says:

    I desperately need a moisturizing lip color that does make my lips flaky. Does the Lippie Stick last for longer than 20 minutes? My other tinted balms don’t. Thanks!

  6. k-t says:

    I am not brave enough to travel in white bottoms or dress. Black or navy, all the way for this klutz. But I am a huge fan of linen shift dresses for summer. I can’t comment on current stock, but J Crew Factory, J Crew, and Gap all had them this summer (not sure on the pockets this year; I know the JCF and JC ones did in past years), and Tommy Bahama has one with a split neck.

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