What to wear for sigthseeing is a good question. Who isn’t looking forward to travel and see new cities. Read what to pack for a safe and comfortable sightseeing experience no matter what the weather will be.
- What to Wear for Sightseeing on Vacation and on the Side of Business Trips
- Go for Stylish Walking Shoes
- When Touring Museums Have a Cover-up
- A Pocket Umbrella or Packable Rain Jacket Save the Tour during a Shower
- Skirts May be Tricky with Walking Shoes
- A Safe Bag Is a Must
- Protect Your Skin, Eyes and Sunglasses
- Photo Inspirations for Sightseeing Looks
What to Wear for Sightseeing on Vacation and on the Side of Business Trips
With the vacation season right around the corner today’s post focuses on sightseeing outfits. Even when your your vacation asks for resort style plan at least for one sightseeing look. There will be a day too cold for the beach, but perfect for exploring the town. Also plan an outfit or two also when you pack for a cruise. When your sightseeing is related to the evenings while on a (science) conference plan your wardrobe accordingly so you can swap fast from business casual style to a walk around town.
Go for Stylish Walking Shoes
Sightseeing in metropolitan areas typically includes being on public transportation and on your feet a lot. Comfortable, chic shoes that you can walk in are key. Of course, you can rely on your running shoes. However, waterproof sneakers or walking shoes are a much more stylish option. In summer, comfortable sandals may be a good choice too when the weather is dry.
Pro tip: Never take a tour with brand new walking shoes. It’s a recipe for blisters. Walk them in in the weeks prior to your tour.
When Touring Museums Have a Cover-up
Visiting museums and galleries means air conditioning, while it may be hot outside. This is especially true when sweating in clothes during the dog-days. Thus, go for a shirt/top plus sweater or cardigan or casual jacket combination to not catch a cold. You can knot the cardigan or sweater around your waist or shoulders for style when outside and pull it on inside to stay comfortable in the chill of the AC.

A Pocket Umbrella or Packable Rain Jacket Save the Tour during a Shower
If it rains, have a light weight rain jacket or trench coat handy. You can check the wet jacket or coat with the coat clerk when visiting a gallery/museum. A pocket umbrella is an alternative, but will be difficult when you need both hands for pulling maps on your cell phone. Color is great to up your style and mood in rain.

Skirts May be Tricky with Walking Shoes
Most skirts don’t look great with walking shoes or flats. Thus, safe options are jeans or chinos depending on the temperatures. In both cases, opt for a loose/relaxed cut for your pants. It is just so much easier to walk up the stairs in the tower of Cologne Cathedral in a relaxed cut than in skinny jeans.

A Safe Bag Is a Must
Sure, you want your hands free to take photos with your iphone, to check the map for orientation to find the museum, hold the museum guide or whatever. A funny pack screams tourist. Not to mention looks easily frumpy. Nevertheless, for your bag stay away from backpacks. You risk to throw something down when turning around in a museum/gallery. It is also an annoyance when you wear it in public transportation.
You may hit it in kids’ faces.
Go for a cross-body bag. It is stylish and leaves both hands free for checking the google map and directions on your cell phone, holding the catalog, taking pictures, carrying your latte or ice-cream cone, handling the metro ticketing machine or holding on to a handrail on the train. Furthermore, it doesn’t scream tourist like a funny bag. A wrap scarf purse is a safe travel alternative to a funny bag.
Protect Your Skin, Eyes and Sunglasses
Add a nice necklace or scarf for style. On sunny days, make sure to put on sun cream and wear sunglasses. Reapply often as sun screen rubs off on clothes especially when you are on packed public transportation. Protect your sunglasses with a box from getting scratches when you don’t wear them. Scratches impair the protection of your eyes.
Photo Inspirations for Sightseeing Looks
Here are some visible inspirations what to wear when sightseeing.




You may also want to check out the Dress for Success post on what to wear when travelling.
Enjoy exploring a new town.
What is your favorite thing about sightseeing? What is your favorite outfit for exploring a new place?
When you liked the outfit recipes of this post, and want recipes for all kind of dressing situation in midlife, buy my book How to Dress for Success in Midlife.
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P.S. If you liked any of these outfit inspirations, it would help me if you pinned them to your own Pinterest board. It’s a great way that your friends, family, and others can see them too. Thank you! <3
Photos: G. Kramm
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