Your Guide to the Comfiest Wardrobe Ever

How to Build Cute Comfortable Outfits

I’ve often heard people say, “I want to look cute, but I’d rather just be comfortable,” as if the two are opposed.  I’ve also had people from different walks of life ask me the comfort question: “What can I wear to be comfortable all day?”  I’ve heard this from stay at home moms, women in offices with long days, teachers in classrooms with little kids and have to bend down and move a ton, and college students who spend long days on campus.  Well, if you’ve ever wondered that or ever thought looking cute and being comfortable were mutually exclusive, I have GREAT news for you.  You can have both!

In the past I used to consider “comfortable” to be “not uncomfortable.”  Like, if the garment didn’t bother me I considered it comfortable.  These days I would call that neutral rather than actually comfortable.  My bar is a little higher now.  Now when I say something is comfortable, I mean that it feels like or almost feels like pajama level comfort!

Lately I’ve found quite a few pieces that are this level of comfortable. While I talk about them through out this blog, today I’m consolidating them into one post so that they’re easy for you to access.  (Whenever I find more after this post goes up I’ll probably continue coming back here to update it with new finds.)  Here they are!

For sizing references, I’m 5’6″ with a shorter torso.  I’m normally S/M or 6/8 and size 8.5-9 in shoes.  

Jeans and Pants

most comfortable pants and jeans

Wit & Wisdom Bootcut Jeans – size 8
These are shown above in the middle picture.  I’ve talked about them so much and said they feel like yoga pants.  Tons of you have written to me telling me how much you love them!  A couple handfuls of you have even told me you bought them just to challenge the yoga pants claim and were delighted to find it’s pretty true.  Haha, I love it!

Now, are yoga pants still better?  Yeah, pretty much always.  These are still jeans with a button closure, you know?  But they have elastic in the waistband which is a huge plus, and the material is stretchy all through out the leg and really soft!  And I’ve done all sorts of stretches in them to test them out, and just because you can.  They are so comfortable!

These just got fully restocked!!!  Find them HERE.

Skinny Jeans – Caslon, Paige, Kut From the Kloth, or Wit & Wisdom
I recently wrote a post called “Denim Brands I Love” (HERE) that talked about SOFT, STRETCHY denim—something I didn’t believe existed! The Wit & Wisdom boot cut jeans above were included, but I also talked about other brands and specific jeans within those brands that fit the bill.

Two caveats: 1) These brands are honorable mention. I wouldn’t say they’re like yoga pants, but for skinny jeans they are pretty comfortable. 2) Not ALL jeans from each of these brands are the same comfort level even within the same brand. For example, I’ve found some super soft and stretchy jeans from Caslon, but other Caslon jeans are the neutral kind of comfort I spoke of earlier.  Same case for all of the brands I named above.

  • THESE Caslon jeans
    are soft and stretchy, but personally I find them too stretchy!  Is that possible?  Yes, because they kind of fall off me.  That will not be the case for everyone, as it
    is dependent on your own body shape and how it matches with the jeans.
  • THESE black Paige skinnies
    are very soft, stretchy, and maintain shape through multiple wears.  Many people say they don’t feel like jeans, and I’d agree because of how soft they are.  These are shown above in the third pic with the olive blouse.
  • Wit & Wisdom
    skinnies are HERE, black HERE, grey HERE, but while they have the elastic waistband like the boot cut jeans and have some stretch, I don’t think they’re as soft.  Reviewed HERE.
  • THESE Kut From the
    Kloth skinnies are nice and thick and quite soft and super stretchy!  Other KUT jeans haven’t been as soft.  These Diana jeans don’t fit me well (the rise is too high
    for me) but they seem to fit hundreds of other people perfectly.  Try these!  Size 6 fits me best.  Reviewed HERE.

This pair is shown in the first pic above with the blue pumps.  I’ve always had a battle with trousers because they squeeze me in awful places.  Finding this pair opened me up to a whole new world of trousers–ones that felt like yoga pants but were also thick enough to smooth your lumps!  Honestly, these might be more comfortable than the Wit & Wisdom jeans I just talked about.  Read my review of them HERE.

Black Trousers – Vince Camuto – size 8

This is similar to the pair above, but whereas the zipper is on the side for the pair above, these have a zipper and tab closure in front.  Another great, super comfortable pair of trousers!  They also come in grey.  More detailed review HERE.


how to look cute and comfortable

Maxi Dress – size S
I know the weather is getting cooler so a sleeveless maxi dress might not be on your radar, but I have to mention it.  I have it both in black and the blue print as shown in the first two pics above.  They are soft and stretchy and wonderful!  They are are not thick, but they are a thicker than other maxi dresses and skirts I’ve tried, so I prefer these.  A lot of you have written saying you have and love them as well.  They come in 24 colors and prints (!!!), and they are constantly getting restocked or new colors and prints.  See them all HERE.

Jersey Dresses
I have several jersey dresses from Target and Old Navy, 3 of which are shown above, and they’re all made of similar material. They usually feel like the maxi dresses above, just shorter.  They are SO comfortable!  They look cute by themselves with a pendant or statement necklace, or you can layer any jacket, blazer, vest, or cardigan over them.  They also work with ankle boots or riding boots.  They’re totally versatile and something I would definitely wear if I had a long day and needed to be comfortable.

THIS striped dress from Target is a fantastic example.  I’ve talked about it before and how you should not be put off that it’s a maternity dress.  It fits exactly like a regular dress, and maybe even better.  Small fits me best, while medium is a bit of an oversized swing dress look on me.  Old Navy usually carries them, like THESE and THESE.

THIS dress is SO soft and stretchy!  And it’s a cross-front so it’s extremely friendly for breastfeeding!  You can dress it up for work with a blazer or cardigan and pumps, or you can dress it down with a denim jacket and boots or flats.  It’s currently sold out, but with ModCloth you can request for it to come back.  I’ve seen them bring back items that are in high demand, so it’s worth trying because this dress is AMAZING!  For more of the same kinds of strechy, comfy dresses see HERE.

Jersey Skirts
I’ve seen these both in a-line and pencil silhouettes, and just like the dresses above these are super comfy. I have a striped pencil skirt made of super stretchy but thick material, which is not available anymore.  My white skirt above is  from Asos. And many, many maxi skirts tend to be made of this material.

Spotted Dress – size M
I just got this and haven’t taken outfit pics with it yet, but a remix with it is soon to come.  This is NOT the same jersey type of material that the previous three mentions are made of.  It feels more suited for work wear or dressing up but is just as soft and stretchy as the jersey stuff!  Super great option for work or dressier events!  Find it HERE.

the most comfortable tops
Madewell Tee – size S
These are the olive tee on the top right and the grey tee on the bottom right above.  They’re literally pajamas for me since I sleep in the grey one!  And I wear it out.  Hehe shhh, our secret!  This is my favorite grey tee because of the fit and the heather grey.  It’s soft and, at least on me, has nearly the perfect drape for a loose fit.  I definitely recommend these tees, especially the grey one!

Knit Tops 
There are some tops that feel like t-shirt material but have extra details that make them look a little more polished or put together.  They might have a print, or drape differently than a t-shirt, or have pleats, or some cutout or lace details, etc.  The long sleeve olive one above and the printed navy one in the middle are just two examples.

  • The printed shown above can be seen better HERE but has been long sold out.  You can find a bunch at ModCloth HERE for ideas of what’s out there.  
  • The long sleeve olive one on the left can be found HERE.  Very soft and stretchy.
  • The black one under the cardigan is very similar to the olive one but short sleeved.  A very similar one to the one I own is HERE
  • Another example that’s a tank instead of a tee is a black and white striped one HERE.  That one looks super easy and comfy to wear.

Completer Pieces

really comfortable blazers, jackets, and cardigans

Knit Blazers – size S
I’ve heard tons of people say blazers aren’t comfortable because they feel bulky or constraining or stiff.  The great news is that there are some blazers that feel like sweatshirts!  While they probably won’t work for a business setting, they are great for business casual settings, being on campus all day, or chasing kids.  You can wear these with jeans and blouses for more casual business casual settings, or a t-shirt, jeans, and flats for campus or childrearing.

I own THIS blazer from the NSale, shown on the very left above, and can vouch for its comfort.  I was surprised at first by how thin it was, but I got over it because it’s so comfortable.  Another one that I *think* is the same or similar material is HERE.  I think I have the older version of this one (shown HERE).

Soft Sweater Cardigans – size S, could do XS
This is the tan one shown above, and I have it in maroon.  These are cozy layers to add on top of other comfy clothes.  I got these during the NSale and it’s been too hot to wear them, but they are fairly soft.  Could be softer.  BUT, the reason these make the list is because I’ve tried a lot of sweaters like this that are heavy, so that makes them uncomfortable to wear all day.  These are relatively lightweight!  They sold out quickly during the NSale but are back in stock in many colors.  Find them HERE.

Most cardigans are pretty soft and easily wearable all day.  If it’s not, look for another one because there are plenty out there.  Ones currently in my closet are from H&M, Nordstrom, and ModCloth.  H&M ones have held up for about 7 years each with many washes and no pilling.  I have 7 of them in 3 different cuts!  Target cardigans have pilled or fuzzed after just 1-2 washes, so I don’t bother with them anymore.  I own the same ModCloth cardigan in mustard yellow (HERE) and teal (HERE).  They are new in my closet so I haven’t washed them yet and can’t speak to pilling.  But, ModCloth cardigans are the softest and thickest of these brands.  I think there are softer ones at Nordstrom that I haven’t tried yet, but they are more expensive than any of these.

Utility Jacket – size S, could go for XS
I talk about utility jackets quite often as one of my favorite and most used pieces in my closet.  I’ve often gotten questions about whether or not you can wear them all day, since people’s experiences with jackets tend to be too uncomfortable for that.  My answer is that it depends on the particular utility jacket as they are not all equal.  The one I own (no longer available, received years ago) is flexible enough that I can wear it all day.  Many other similar jackets I’ve tried are too stiff and I don’t think I could wear those all day.  However, one of the jackets from the NSale (HERE) was suuuuuuper soft and flexible–even better than the one I’ve been wearing all these years!

That is just to say that it is possible to find a utility jacket that is ultra comfortable!  My experience is that it’s rare to find this unless you pay more than average for it (average being ~$30-40), but it is possible.


the most comfortable shoes

UGG Wedges – size 8.5
I’ve said many times that these are the most comfortable wedges I’ve ever worn.  This is another item that several of you have confirmed are incredibly comfortable.  I have walked for hours in these and not skipped a beat which is amazing because these aren’t flats either.  They are not just “not uncomfortable” but they are actually comfortable.  They’re really easy on your feet, and the sole is flexible to walk in.

These are almost sold out, but I tried another pair of UGG wedges that were equally as comfortable.  Some UGG shoes are really not comfortable, but seeing as how my pair is not the only one that I’ve found that was ultra comfortable, I believe it’s worth looking at UGG for comfy shoes.

Clarks Booties – size 9
These get honorable mention.  They are the most comfortable booties I’ve tried because 1) they have a little bit of padding, 2) the material is actually nice to your skin and doesn’t rub it harshly, and 3) the material is also flexible for a bootie, and 4) the sole is rubber.  The one reason they’re only honorable mention is because I find them to be heavy.  That’s not the easiest to walk in for hours, and that’s what it would take for a shoe to make this list.

White Sneakers – size 8.5
This should really be expanded to “most sneakers,” but I’m honing in on these because I own the older version of them and they are my go-to sneakers.  I’ve tried the newer version (the one I linked), and I think my older version is slightly more flexible regarding both the top of the shoe and the sole.  But, the newer version is still very comfy and flexible, and I believe it will flex out and soften even more with more wears.

I LOVE how sleek of a profile these are.  I have the perforated pair, btw, not the totally smooth white pair.  I love that the perforation gives it some character and visual interest.  These are very easy on the feet, and they are incredibly easy to style!

I wear them with THESE socks.  Please note the black snakeskin pair is not as flexible on the top as the white perforated pair.  I haven’t tried the black perforated pair though.  See all the ways I’ve worn them HERE.

Hue Leggings – size S
I was avoiding the legging route for this list, but if you want a rec for one here’s mine.  I sleep in these!  In terms of if they’re see-through, my take is it depends who you ask.  I believe that depends on your body shape and how it fits with the size legging you get.  If a pair *barely* fits you in that size that means the material is stretching thinner to cover you, so it’s more likely to be see through.  If the pair has more give, the material stretches less and stays more opaque.  In size small, if I bend over too far then they are mildly see-through.  In medium they are not see through at all…but they are also way too big with too much extra material for me.  If you’re slightly larger than me, the medium might fit you perfectly, not stretching too thin and not having too much material.  Know what I mean?  Hope that makes sense!

But ultimately, they are very comfortable and mostly maintain their shape after lots of wears.  Thousands of people loooove them, including me, and people particularly love the wider waistband.  I thought I would hate that kind of waistband, but it turns out that it won me too!

You can wear them with one of the Madewell tees I linked earlier, the sweater cardigan, and the white sneakers for the ultimate comfy casual look!  Find them HERE in black, brown, and grey.  (I can only speak for the black pair regarding opaqueness.)

Outfit Examples
While these kinds of pieces may not be able to make up the entirety of a wardrobe, especially if you need business casual or professional looks, you CAN make outfits out of just these pieces or mostly these pieces. If you need inspiration for how to work some of these pieces together, here are a few outfits that are primarily (or entirely!) made up of the comfy pieces we just talked about.

cute comfortable outfits - really comfy!

I hope this has helped in some way inspire you that you can dress cute and still be extremely comfortable! Good luck!

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