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Sharing tips and outfit ideas on how I dress stylish while still staying comfortable!

Happy Monday friends!

I hope you all had a great weekend. My weekend consisted of having a few drinkies with my college bestie who was in town for the weekend, catching up on some wedding planning, and attending Trev’s annual firefighter summer picnic. I feel like life just needs to slow down, anyone else feel me?! I’m excited to get back to the old Monday grind. Let’s dive into today’s post!

How to Dress Stylish While Staying Comfortable | InspirationIndulgence.comHow to Dress Stylish While Staying Comfortable |

One of my hugest pet peeves is wearing anything that is uncomfortable. This probably accounts for a few reasons why I: A.) Wear sweatpants basically 99% of my existence; B.) I seldom wear jeans; C.) I don’t do stilettos. Like ever. LOL.

The truth is, I like my fashion to feel low-maintenance when I’m on-the-go. But sometimes, dressing stylish yet comfortably can be a struggle. However, it doesn’t always have to be this way! Don’t believe me? Read on…

How to Dress Stylish While Staying Comfortable |

Tip #1: First of all, think of where you’re going. Are you really going to want to wear this outfit all day/ night if it is not comfortable? Know your limits!

Where are you going? What are you going to be doing?

Are you going to be running to the bank followed by the grocery store? Or are you going to a casual backyard BBQ bash? A graduation party? A wedding?

For example, as I mentioned above, I don’t do stilettos. But let’s be real. Stilettos don’t do me. I’m super clumsy. I have tried wearing stilettos to a wedding before and it resulted in kicking off my shoes before I even finished my dinner. As for casual day-to-day errands, I’m not high-maintenance enough to ever WANT to wear heels during these meticulous chores. That’s what Converse were invented for, DUH.

Which brings me to my next point…

Tip #2: Ditch the heels, when at all possible.

Heels always make me feel sexy, but I don’t need them for all occasions. I don’t wear them when I’m shopping, running errands, or even meeting up with friends. I pretty much only wear heels when I’m going out at night. But this is just who I am; if you love wearing heels and find you can easily walk in them, all the power to you!

There are endless options of super cute shoes you can wear if you’re going for a more casual look. My favorites include Converse, laceups such as these sandals from American Eagle (which are currently on sale for only $12.99!), these adorbs Adidas sneakers, or even a casual pair of flip-flops.

How to Dress Stylish While Staying Comfortable | View More:

Tip #3: For more important events, do a trial run.

There have been times when I wanted to wear a dress to a wedding but wasn’t sure how comfortable I would feel in it. I would advise you to “pretend” wear your outfit for at least one hour prior to leaving for your event. If you find yourself getting annoyed with constantly pulling your straps up/ pulling your jeans up/ taking off your shoes, etc…you probably shouldn’t wear it.

Tip #4: Remember- dressing comfortable doesn’t have to be drab.

When I think of dressing comfortably, I immediately think of jumping in  sweatpants or yoga pants. Of course, dressing for comfort doesn’t always have to be drab. My go-to look when I’m running errands and still want to look cute is something similar to what I’m wearing in this post; a light summery dress with cute sandals. Casual, yet simple.

Scroll down for a few more cutesie outfit ideas for comfort!

How to Dress Stylish While Staying Comfortable | How to Dress Stylish While Staying Comfortable |

When it comes to stylish comfort, should you wear it or ditch it? I give my two cents…

Wear it //

Ditch it //

    • Anything strapless
    • Heels
    • Suits
    • Crop tops
    • Tight jeans
    • Cold shoulder tops (these always seem to require lots of adjusting)
    • Anything revealing that would possibly make you feel insecure or uncomfortable

How to Dress Stylish While Staying Comfortable | InspirationIndulgence.comPhotos by Shaunae Teske // Dress: Livin’ Feely Shop; Tote: Target; Sunnies: Ray-Ban; Shoes: Charlotte Russe; Earrings: Happiness Boutique; Bangle: Happiness Boutique

How fun is this outfit? The dress is from Livin’ Freely Shop, my newest boho go-to boutique. My jewelry is from Happiness Boutique, which I featured in my last blog post on how to wear statement necklaces! Not only is this dress super adorable, but it’s comfortable. It was about 80 and humid when we shot this look; this dress was made for a hot summer day. After shooting I ran errands for the rest of the day and felt very relaxed and low-key.

What is your go-to outfit when you want to feel comfortable, yet still look cute? Leave me a comment below!


  • Summer dresses are definitely my favorite thing to wear when I want to look nice but still feel comfortable! Also, I love everything about that outfit, you look so pretty! :)

    • Aw thank you so much, Tami! xo

  • Yes! And I love that dressing comfortably doesn’t mean it has to be slouchy and ugly. There are so many cute clothes nowadays that are comfy too. Win-win!

    • Yes! Slouchy is exactly the word I was looking for! haha

  • Yas, girly!! SO good. I’m all about comfort when it comes to style! There are so many ways to dress nicely, while being casual and comfy at the same time.

    • I just love wearing cotton T-shirt dresses….I feel like I live in them!

  • Zana Djakovic

    You look so so chic Chels. Love that outfit. Fashionable, indeed!! And yeah it looks so comfy. I am all about comfy clothes too lately. The dresses are my everyday choice and sandals. Thanks for sharing this post!!! :)

    • Thanks so much for stopping by, Zana! xoxo

  • stylish and comfortable are my go to’s! that’s the only ways i like to dress lol!

    • Right. I can’t stand discomfort!

  • I won’t wear anything if it’s uncomfortable. Cotton is my go to!

  • Kristen Jones

    Your earrings are SO cute! I need to learn to stop wearing heels so much, but I just love them! lol!

    • I wish I was as graceful as you! Hey, own it, lady!

  • These photos are gorgeous and you look beautiful! The older I get the more concerned I am with wearing heels all the time. Comfort is key especially when you’re gonna be out and about all day!

    • That’s how I feel! The older I get, I’m over it! lol

  • Anna Hubbard

    Very pretty dress and great tips! My favorite way to stay stylish and comfortable during the summer is by throwing on a cute dress!

    • Yes ma’am!! Something comfortable!

  • These are all great tips! I am allll about being comfy, so I’m always looking for stylish pieces that are still comfortable :)

    Kristen |

    • Thanks so much for reading, Kristen! xo

  • Adriana

    I LOVE this! Comfort is always key for me but I love to be comfy haha so this is great!

    • Aw thank you so much, Adriana! You’re always so sweet!

  • I’m all about ditching the heels too! Being comfortable is number 1 to me!

    • Right! Thanks so much for reading, love!

  • That is such a fun look! I love the earrings!

    • Aren’t they fun! Thanks so much, lady! xo

  • Elizabeth Johnson

    That dress is amazing! Love it! You always look fabulous! I too don’t like to wear uncomfortable things. I don’t mind heels. I was in a ballroom performance group in college as well as a dance major so my feet have taken a beating. However, I do walk around the store for a while with heels to make sure that they are comfy!

    • Thanks so much for reading, lovebug! It’s always good to practice walking in heels before wearing them out! hehe

  • Comfort is key, especially in the disgustingly hot summer months in Miami. I find my go-to is a black tshirt dress and my baby pink Adidas.


  • Same! Comfort is a huge must of mine!

  • Love these tips! I’m definitely all for comfort, and ditching heels is probably the easiest way to do that!

    • Right! I’m not quite sure why they were ever invented! lol

  • That trial run tho – so huge! The WORST feeling is wearing something for “the real deal” and feeling awkward the whole time…try it first!

    Coming Up Roses

    • Right!!! One time I wore a dress to a wedding without doing a trial run and it had the worst static cling…kept clinging to my butt the whole night! Embarrassing!

  • Your tips are totally on point! You look so fantastic too! Comfort is a necessity for me!
    xo Debbie |

    • Aw thank you so much, Debbie! xo

  • Taylor Smith

    Those earrings ARE SO FUN.

    • Thanks so much for stopping by, Taylor! xo