5 Awesome Ways to Look Polished AND Feel Comfortable

Do you think it’s possible to look put together and still feel comfortable? It’s a question I’ve been asked many times. As the creator of The Confident Closet, I often hear from women that they don’t want to get dressed in “real” clothes because they just want to be comfortable.

This has always been perplexing to me. It’s like everyone thinks being comfortable and looking polished are mutually exclusive.

Over the past five weeks of quarantine, I’ve been hearing the same thing on the regular from my Instagram community. (Join me here!) Some ladies are rocking it in their PJs and doing just fine, while many others have shared that they must get dressed everyday to feel the slightest bit productive. There seems to be a big divide between what we perceive as looking put together and dressing for comfort.

And to be honest, I didn’t really have a great solution to share with anyone.

Until now.

It really is possible to look put together and still feel comfortable!

Throughout these five weeks of quarantine, I’ve been paying attention to how to look put together and still feel comfortable, and I’ve found five pieces that have absolutely done the trick for me. I’d love to hear what you think of them!

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5 pieces that can help you look put together and still feel comfortable

Put together and comfortable piece


#1: A casual jumpsuit 

Admittedly, it’s taken me awhile to jump into the jumpsuit trend (see what I did there? Ha! Are mom jokes a thing?), but I  am in L. O. V. E. with this incredibly comfortable jumpsuit I recently purchased from Talbots.

July update: Sadly, this jumpsuit in the photo is already pilling, and I’m not sure it’ll look great for next year. Instead, I recommend this gorgeous navy jumpsuit from Boden – a retailer that has never yet let me down when it comes to quality AND style! 

A monochrome jumpsuit is my favorite way to look put together and still feel comfortable
This jumpsuit is as comfortable as my fave pair of PJs!

One of the best things about this item is that one-piece dressing makes looking put together SO easy.  I mean, there’s not even the concern about how to properly match a top and bottom! #winning

Monochrome dressing (wearing only one color) is also extremely flattering to your overall silhouette, as it draws the eye up and down. A long vertical line creates an elongated and slim appearance. 

Another element about many jumpsuits that I love is the belted waist. This is a hugely flattering feature, as it creates a strong horizontal line at the natural waist.

There is a very simple but little known fashion recommendation called the Rule of Thirds. Basically, anything divided into thirds will be more pleasing to the eye. (Photographers, you know what I’m talking about right?!) Often our natural waistline sits right at the top third of our body (from shoulders to ankles), and our hips and legs comprise the other 2/3 of our silhouette. Creating a visual break at the natural waist is a great way to flatter our overall appearance.

Finally, this casual jumpsuit coordinates perfectly with the comfiest of shoes: the little white sneaker.  It can be dressed up easily with sandals and jewelry, but if comfort is your game, stick with the sneaks and you’ll be all set! 

As far as dressing to look put together and still feel comfortable, the casual jumpsuit is at the top of my list. 

Put together and comfortable piece

#2: Maxi skirt 

A long, high-waisted maxi skirt is one my ultimate faves to look put together and still feel comfortable! 

In my honest opinion, it’s way more comfortable than leggings! There is no need to adjust or tug at the seams and nothing is compressed. 

A simple maxi skirt is super versatile and comfortable!
This maxi skirt goes with everything.

This particular style with its high waist and simple lines is very flattering for most body shapes.  

My favorite way to wear a maxi skirt right now is with a fun graphic tee half tucked at the waist. Then I pair it with my favorite white sneakers and voila! Put together and comfortable times 1000. 

Maxi skirts are also so great because they can coordinate with so many different pieces. Try pairing one with a super casual tee or a chambray button up shirt tied at the waist.  

For shoes, of course pair that maxi skirt with simple white tennis shoes, boat shoes, flats, or your most comfortable pair of sandals. 

Finally, the high-waisted maxi skirt follows the Rule of Thirds that we talked about with the jumpsuit above. There’s no doubt that this piece is a win-win for both fashion and comfort. 

Put together and comfortable piece #3: Relaxed button up shirt

A simple button up shirt can always help you look put together, and adding a relaxed fit to it really increases the comfy factor. 

A simple linen button up is an easy way to look put together
This linen button up is one my most versatile pieces.

My two current favorites are made from linen and chambray – both perfect spring fabrics that coordinate with everything in my closet. 

If you’re not sure how to style a button up shirt, check out these simple options that will help you look put together and still feel comfortable: 

  • leave it unbuttoned and wear it as a layer over a simple tee and leggings
  • tie the two sides at the waist and pair it with a maxi skirt
  • do a simple half tuck into your favorite pair of girlfriend jeans

I also love button up shirts for spring time because they adapt so well to temperatures that may shift quickly throughout the day. You can choose to wear the sleeves long or quickly roll them up when needed. 

Put together and comfortable piece #4: Simple cotton dress

Another great piece for your closet to help you look put together but still feel comfortable is a simple cotton dress. From tee shirt dresses to maxi dresses, there are so many options for great casual dresses available today. 

This simple and easy-maintenance dress is my favorite. I like that it has some shaping to it. The cotton fabric and pockets (seriously, the best thing ever for a casual dress!) make it super functional. I can pair it with tennis shoes or my most comfortable sandals and look polished in just minutes. 

A simple cotton dress is a fantastic way to look put together and still feel comfortable
Pockets on a dress = genius!

I definitely prefer a dress that is semi-fitted and isn’t a giant bag. Wearing pieces that are too baggy tend to make any body shape look wider, which is typically less flattering. 

For a casual dress, choose any length that suits you best. With my semi-petite frame, my best lengths are knee-length and maxi. For those who are taller (5’8”) and above, you will most likely find the midi length to be very flattering for you too! 

There is something wonderful about wearing a dress that really makes it look like you’ve gone the extra mile in getting ready for the day! When people compliment you on how polished you look, you can also silently congratulate yourself on how comfortable you are too! 

Put together and comfortable piece #5: Girlfriend jeans

Oh, hello, girlfriend jeans! I am so thrilled that more relaxed jeans styles are becoming popular again!  Skinny jeans have been THE thing for years now, and while I certainly love them, I am glad for the shift towards something a bit more comfortable too. 

These girlfriend jeans are so great for feeling comfortable.
Girlfriend jeans are a girl’s best friend!

Girlfriend jeans are a slightly more fitted version of the boyfriend jean, which is a style that is cut loosely all the way through the seat and thigh and down through the leg. I often feel that boyfriend jeans are a bit too baggy and can lend themselves to making my silhouette look wider and shorter than I’d prefer.    

That’s why girlfriend jeans are so perfect. They are just slightly more tailored and do a better job of creating a more feminine shape. 

To up the casual factor of your jeans, you might really like the distressed denim look as well. I just bought my first pair of slightly distressed girlfriend jeans. The unfinished hem pairs easily with almost all comfortable tops. While major distressing is not my jam, I was glad to find a pair that was a happy medium between looking more formal and super casual. 

Another really fun trend in jeans right now is the button fly look. This is a perfect way to make your jeans look more casual! 

Finally, I highly recommend looking for ankle length girlfriend jeans. This means that the hem of the jean ends just an inch or two above the ankle. This length is incredibly flattering for every body shape as it reveals the slimmest part of the leg and allows just a bit of skin to show.

Most women should avoid a mid-calf length in jeans (or any pants, for that matter!). When the hem falls at mid-calf, an unflattering horizontal line draws the eye straight across the widest part of the calf and makes it look wider.  

So that’s our round up of 5 clothing pieces that will help you look put together and still feel comfortable everyday! I believe it really is possible to dress casually and feel polished at the same time.

Would You Like to Learn More about Creating the Perfect Wardrobe for You? 

If you are looking for more individual wardrobe tips and advice, or are interested in creating a personalized wardrobe that flatters your body shape and coloring, check out my new course called The Confident Closet! Enrollment will open on Tuesday, May 5th! It would make an awesome Mother’s Day gift, wouldn’t it?!

5 pieces that will help you look put together and still feel comfy everyday

Jen Bradley, the founder of Jen Bradley|MOMs

Hi there! I’m so glad you’re here. I am a mom who believes that meaningful connections with our kids can happen in small and simple ways. Read More …


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22 thoughts on “5 Awesome Ways to Look Polished AND Feel Comfortable”

  1. I love the the linen button up outfit, this article is awesome, help us to remember how well we should always take of ourselves including the way we dress.

  2. Great ideas right here! I really enjoy wearing the girlfriend jeans. Who was your linen button up by? It looked really cool for summer. Thanks so much for sharing!

  3. Great post! I can’t seem to pull the trigger on the jumpsuit, it does look really comfortable though.

  4. I think the girlfriend jeans here would be my fave. Although definitely not as comfy as sweats! I hang out in sweats and a comfy shirt all day. I know I would like the comfort of the jumpsuit, but without easy access to go to the bathroom, that makes it a No for me. As a yogi, I like to be able to do some yoga asana throughout the day, so comfort and movability (is that a word?) are key!

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