8 Ways to Wear Comfy Shoes & Still Look Super Stylish

Because hobbling around campus in uncomfortable shoes is THE WORST.

This post may contain affiliate links, which means we may receive a commission if you purchase through our links. Please read our full disclosure here.

I was four days into my New York City trip when I gave in. I can’t do this anymore, I thought as I hobbled back to my hotel room after a long day. Every tearful step back to my room made me want to throw my helplessly cute, but uncomfortable, high heeled booties into the street.

The next morning, I promptly marched to Fifth Ave and bought myself a pair of Birkenstocks.

This was the first pair of Birks I had purchased for myself. I had actually owned one pair back in elementary school: they were clogs with half of a cow painted on each shoe. Put the shoes together, and it completed the cow. No joke.

You have to see ‘em to believe it:

Cow Birkenstocks

Alas, the days of cow Birkenstocks were in the past. I walked out of the shoe store already wearing my pair of pink Birkenstock Gizehs. Needless to say, my booties were banished back to my suitcase.

Pink Birkenstock Gizehs

Product: Pink Birkenstock Gizehs

After purchasing my new Birkenstock Gizehs, I thought I had condemned myself to a long trip full of lackluster fashion and pitiful outfits. However, I soon came to the realization I could look acceptable – nay, cute – in my Birks. I could walk the streets of New York with pride. Best of all, there were no more tear-filled nights: I could easily get from place to place with no pain.

The lesson I learned in New York followed me back to school. Every time I am on campus, I see students prioritizing comfort when it comes to their footwear. I am no exception; my Birks go everywhere with me. (Here at CF, we’ve done three separate posts on them within the last year or so – the obsession is real.)

Now, there’s nothing wrong with an awesome ankle boot or heel, but if you’re a comfort-first girl like me or just want to expand your comfort-footwear wardrobe, you need to keep reading.

Below, I have chosen four “comfort-focused” shoes I see most around campus (Birkenstocks, Chacos, Tevas, and the classic athletic shoe). I have identified my favorite style from each respective brand and shown how I would style it. Let’s get to it!

Related post: How to Wear Birkenstocks (Styling Guide & Outfit Ideas)


Born in 1774, Birkenstocks first were sold in the United States in 1967. Birkenstocks were first associated with the liberal movement and flower children, who donned these sandals to represent a free-thinking subculture. Today, these shoes are trendy: everyone from high-fashion designers to college students are wearing these cork sandals.

My Birkenstock Picks

Suede Two Strap Birkenstocks

Product: Arizona Taupe Suede Sandal

Mayari Golden Brown Criss-Cross Birkenstock

Product: Mayari Golden Brown Birko-Flor

Pro Tip: Before spending the day wearing your brand new Birkenstocks, break them in a little first. I always found wearing them around the house in short intervals really did the trick!

How I Would Style Birkenstocks – 2 Outfits:

Minimalist Inspired Birks Outfit

Products: Top, Birkenstocks, Jeans, Bag

Updated Birkenstocks Outfit

Products: Dress, Necklace, Birkenstocks, Bag


Whatever college campus I am at, whatever time of day or year, I always see a pair of Chacos.

As we mentioned in our recent Birks vs Chacos post, Chacos were founded in 1989 by Mark Paigen, a whitewater rafting guide. He wanted to design the ultimate outdoor sandal that had both comfort and durability, so he constructed the Chaco sandal with the now patented suction-padded bed.

Today, Chacos are known globally and have a strong reputation with outdoorsmen and college students alike. Though they are made for the outdoors, there is no reason you can’t wear them in everyday life. After all, you’re going to pay upwards of $100 for these shoes – you’ll probably want to get some good use out of them!

My Chacos Picks

Classic Pink Patterned Chacos Sandal

Product: ZX/2 Classic in Limerick Nectar

Purple Chacos Sandal

Product: Z/1 Colorado in Twist Dazzling

Pro Tip: Not seeing a style you love ready to go? You can always customize your own Chacos sandal.

How I Would Style Chacos – 2 Outfits:

Products: TopJeansChacos

Casual Day Out Chacos Outfit

Products: Dress, Jacket, Chacos, Necklace


Tevas were created by a river guide in the Grand Canyon in 1984. The guide attached Velcro watchbands to an old flip-flop, and the Teva design was born.

Recently, Tevas have been gearing towards a more fashion-minded audience with bright new prints, styles, and flatforms.

My Teva Picks

Classic Brown Leather Tevas

Product: Women’s Original Universal Leather Diamond

Tevas Braided Suede Sandal

Product: Women’s Original Sandal Suede Braid

Pro Tip: Want to know how to take your Tevas from summer to fall? Check out this lookbook put together by stylists.

How I Would Style Tevas – 2 Outfits:

Boho Tevas Outfit

Products: RomperBag, Headband, Tevas

Tevas Updated

Products: TopShorts, Earrings, TevasBag

The Athletic Shoe

As every CF reader knows, athleisure is a huge trend this season. In fact, we’ve covered this topic extensively: read here, here, and here.

The biggest offshoot of the athleisure trend is the return of the athletic sneaker as casual wear. There is something so classic about the tennis shoe. It is the ultimate source of style and comfort – and that is why the tennis shoe is everywhere on campus.

My Fashion Athletic Shoe Picks

Adidas Superstar Tennis Shoe

Product: Adidas Superstar

Nike Low Flyknit Shoe

Product: Nike LunarEpic Low Flyknit

How I Would Style Athletic Shoes – 2 Outfits:

How to wear adidas with a denim skirt and striped top

Products: Top, Skirt, Earrings, Belt, Adidas

Nikes Styled with Duster Coat

Products: Duster, Top, Jeans, Nikes


Ladies, if you can make it around in a pair of stilettos, more power to you. However, with today’s selection of adorable footwear, there is no reason why you can’t look darling and wear supportive shoes, if that’s what you’d rather do. It’s totally up to you.

For more on shoes, see our guide to what to do with old shoes.

So, what do you think? Are these shoes as popular at your school as they are at mine? Would you hop on the utilitarian shoe trend, or do you live by your heels?

2 thoughts on “8 Ways to Wear Comfy Shoes & Still Look Super Stylish”

  1. I am definitely a comfort-first girl. I’m so glad the athletic shoe has creeped into casual fashion. My nikes are always with me when I travel. Great post!


Leave a Comment