Is their any better feeling than being comfortable in your clothes?  Seriously.  An elastic waistband, a cozy sweater, soft cashmere?  Yes, please!  Yet, we all know there are times where we may want to feel like we just rolled out of bed but can’t look like we did.  Darn life, always getting in the way of comfort.

With fall around the corner, there are tons of comfortable casual options.  The key to wearing these pieces is to do it without looking sloppy, and the question becomes if it is even possible. Does it have to be a painful compromise?  Well, the good news is there a few little tricks to comfortable casual that will look chic and pulled together at the same time.  Take a look at the examples below for tips and ideas.

Comfortable Casual Without Looking Sloppy

Outfit #1

comfortable casual

In the outfit above, I used this über comfy Tencel wool sweater set of this cardigan and top from Elie Tahari.  I paired it these pieces with lightweight drawstring pants from Theory.  Ahhhh.  Grab a hot cup of tea and wrap yourself in the delightfulness of ease, right?  The look on its own isn’t necessarily sloppy, but it can come across a little laid back.  With a few tweaks this outfit can leave the couch.  The key is found in the final touches and having them be a bit dressier.  For example, I added these sparkly Yosi Samra foldable flats and layered pendant necklace.  That’s all it takes, just a few touches.  Lastly, I used this burgundy tote from Cole Haan for a splash of color.

Outfit #2

casual comfortable

A sweater and jeans.  Does it get any basic?  What separates a sloppy sweater and jeans look and a pulled together one?  Not much, really.  It’s not necessarily the sweater and jeans that make or break a look, it’s what is worn with the outfit that does.

If your comfortable casual sweater and jeans outfits have you bored, uninspired or just feeling like a slob, take note of the look above where I styled these J. Crew jeans and a French Connection sweater with a pair of nude Kristin Cavallari flats, Stella & Dot statement necklace, Karine bracelet, Gorjana studs and quilted structured bag from Rebecca Minkoff.

Try to avoid sloppy accessories, or super relaxed pieces when wearing your sweater and jeans and choose dressier pieces to bring balance to the outfits.

Outfit #3

comfortable casual

The beauty of leggings is they can feel so liberating.  No constricting waistband, they have plenty of stretch.  On certain days this is all you need to power through.  Add a shapeless knit tunic and it’s the perfect recipe for sloth.

If you want to leave the house without looking and feeling like you’re wearing your pajamas, an easy tip is to pair the looseness with more structure.  For example, I added these boots from Sam Edelman to these J. Crew Leggings and shapeless top from Modcloth.   Next, to make the outfit more finished, without diminishing the ease of the look, I wound this silk and cashmere scarf from Nordstrom around the neck.  Lastly, I used this sturdy Allsaints hobo bag and simple earrings from Aqua.  You don’t have to abandon comfort to avoid looking sloppy.

It should also be mentioned, that adding these small elements to your comfortable casual outfits you won’t only look more pulled together but you will feel this way too.  This can make a huge difference in how you carry yourself and put yourself out there.  Try adding some small dressier touches to your easy looks and notice how much better you feel.