Affordable & Comfy Outfit Ideas for Sightseeing In the City

Huge thanks to JCPenney and ShopStyle Collective for sponsoring this post

I know you love packing lists and outfit ideas for spring trips, so today we’re back with some super affordable outfit ideas for sightseeing in the city, and I’m partnering with JCPenney and ShopStyle Collective to do it!

JCPenney is one of my go-to stores when I help friends with style because they have incredibly affordable clothes that are also comfortable. They carry one of my favorite brands for stretchy denim that won’t break the bank, comfortable and stylish shoes, and a whole lot more! JCPenney also carries a range of sizes, including straight, petite, tall, and plus. And, you can shop online, in store, or shop online and use the free same-day pickup service to conveniently grab your order. So, if you want comfortable clothes that are friendly on your wallet, you should definitely be shopping at JCPenney!

And, JCPenney is currently running a Friends & Family promo so you can get an extra 30% off select apparel, shoes, accessories, fine jewelry & home until 5/1 with the code FAMILY9!

Casual Comfortable Clothes for Travel

Shop the Outfits:
Outfit #1: Tee | Leggings | Anorak | Anorak (similar) | Fanny Pack | Sneakers
Outfit #2: Tank Top | Denim Jacket | Jeans | Backpack | Sandals
Outfit #3: Tee | Joggers | Sandals | Sneakers
Outfit #4: Tee | Joggers | Backpack | Sandals
Outfit #5: Tee | Bomber Jacket | Black Pants | Backpack | Footbed Sandals
Outfit #6: Tank Top #1 | Tank Top #2 | Denim Shorts | Fanny Pack | Backpack | Footbed Sandals

I created a few outfits that you can wear on a trip to the city, from super casual, comfy, sporty looks to some nicer casual outfits that still allow you to be pretty comfortable. And of course, you don’t need to be on a trip to wear these—they’re good for everyday life, too! 😊 Let’s talk through each of them briefly below!

SIZING INFO: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.

Clothes for Traveling and Sightseeing Sporty and Active: light brown cropped tee + black leggings + light grey raincoat + black hip pack + black sneakers

Outfit #1 – Sporty & Active
Big day with lots of walking? Go for a sporty look, but upgrade it with a cute sporty tee like the Crew Neck Short Sleeve Crop Top by Stylus. The cropped silhouette of this tee gives it a fresher and more current feel. It looks so comfy and comes in 3 colors, HERE! Pair it with high waisted leggings so that you’re not totally exposing your midsection and top it off with a pair of comfy sneakers. These Demi Sneakers by Stylus have 4.8 stars (!!) for superb comfort, but they are only $27.99 right now!! Find them in 4 colors, HERE.

Throw on another layer as needed, like the Free Country Waterproof Lightweight Anorak if there will be spring showers. If a raincoat isn’t necessary, try the Stylus Lightweight Bomber Jacket instead!

Top it off with the Stylus Fanny Pack, which allows you to be hands-free without the strain on your shoulder that a crossbody can give. This one is super affordable at just $12.60(!!) with the code FAMILY9 and comes in black and pink, HERE!

Shop the Pieces:


Clothes for Traveling and Sightseeing Nice Casual: light brown square neck tank + denim jacket + white straight leg jeans + tan backpack + neutral slide sandals

Outfit #2 – Nice Casual
If you want to step up your casual look a bit, pair jeans with a cute tank top and sandals. Try a pair like the High Rise Straight Leg Jeans by a.n.a which, again, create a modern silhouette. While I haven’t personally tried these jeans yet, the brand a.n.a typically has stretchy denim at really affordable prices. This pair is just $13.99 until 5/1!!!!

You can combine it with any top, and here I’m showing the a.n.a Square Neck Tank Top, which fits loosely around the torso and should keep you comfortable. It comes in several colors, which you can see HERE.

If you’re looking for an affordable denim jacket, the St. John’s Bay Midweight Denim Jacket has good reviews for being comfortable!

Finally, top it off with flat sandals that have a sleek design and go with everything, like the Arizona Kramer Flat Sandals! They are just $17.49 right now and come in tan and white, light pink and snakeskin.

Shop the Pieces:


Clothes for Traveling and Sightseeing Relaxed Casual: white tee + olive joggers + cognac backpack + neutral slide sandals + grey sneakersClothes for Traveling and Sightseeing Relaxed Casual: tan polka dot ruffle sleeve tank + olive joggers + cognac backpack + neutral slide sandals

Outfits 3 & 4 – Relaxed Casual
You can also try a look that’s between athleisure and nicer casual looks, like a t-shirt with comfy, soft pants. Go for a basic top, like the Stylus Crew Neck Short Sleeve T-Shirt in Outfit #3, or try one that has more details, like the Stylus Round Neck Short Sleeve Tank Top in Outfit #4, which has a print and cute flutter sleeves.

For soft pants, try something like the St. John’s Bay Mid Rise Linen Jogger Pant or the Stylus Mid Rise Jogger Pant, which both come in 4 colors.

As for bags, another option that allows you to be hands-free is a cute backpack, like the a.n.a Erika Backpack, which comes in both cognac and black and has great reviews with 5.0 stars!!!

Shop the Pieces:


Clothes for Traveling and Sightseeing Athleisure: white tee + black pintucked joggers + light grey knit bomber jacket + tan backpack + black footbed birkenstocks

Outfit #5 – Athleisure
For another super comfortable, low-key outfit, go for straight leg joggers and a comfy tee. These Stylus Pintuck Joggers with their straight leg silhouette have 4.8 stars! Reviews say these joggers are SUPER COMFY, wash well, and stretch with movement, and they have an elastic waistband, making them GREAT for sightseeing in the city! Reviews also say to size down. These come in 3 colors and are just $21!

If you need a layer, add the St. John’s Bay Midweight Denim Jacket or the Stylus Lightweight Bomber Jacket.

For footwear, I opted for the Arizona Fireside Footbed Sandals, which I own. They are fairly comfortable, really affordable, and come in 7 colors, including a leopard print version. See them all HERE. You can see them on me HERE.

Shop the Pieces:


Clothes for Traveling and Sightseeing Cute and Casual: black square neck tank + light brown square neck tank + denim shorts + tan backpack + black fanny pack + black footbed birkenstocks + taupe footbed birkenstocks

Outfit #6 – Cute & Casual
Last is another cute and casual look, and I’m showing two versions of it. One shows the a.n.a Square Neck Tank Top and the other has the black version of the a.n.a Square Neck Sleeveless Tank Top which is super similar but slightly different. I paired them with a.n.a High Rise 5″ Denim Shorts, which come in 3 colors. Again, while I haven’t tried them personally, a.n.a tends to have jeans and shorts that are pretty stretchy!

For an alternative to shorts, try the a.n.a Boyfriend Jeans, which I personally own. They are fairly thick and help you feel secure while being stretchy at the same time! I wear those in size 4, as they run fairly large. You can see them on me HERE.

I’m showing two versions of this outfit with the same top in different colors and how I’d accessorize each accordingly.

Shop the Pieces:

There are plenty of other tops you could swap in for the square neck tank top, so I rounded up a few in the widget below!

Those are a bunch of outfits you can wear during a trip to sightsee in a new city. And of course, if you’re not going on a trip, you can still wear these to feel cute and put together this spring, wherever you are!

Do you have the right building blocks in your wardrobe to create loads of outfits easily? Grab your free Wardrobe Staples Mini Guide to make sure you do! Plus, you’ll get 6 plug-and-wear outfit formulas to help you mix those wardrobe staples with some of the other pieces that are already in your wardrobe.

Click HERE to enter your info and download your free copy!

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