weekend outfit ideas

5 Comfy Weekend Outfits for Fall That You Won’t Look Sloppy In

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Comfy and cozy outfits will always be on our brains, whether we’re in a year of lockdown or not. And thankfully, this fall is different. Events are back on and our calendars are filling up with fun activities to do. The weekends bring shopping for fall decorations and long overdue coffee dates, instead of the usual solo house hang. Before, we could totally get away with wearing our paint-splattered sweats and too small tees all weekend because no one was going to see us. But the goal this fall is to look stylish without completely sacrificing the comfort we all came to know and love. Thankfully, you can do achieve both with these comfy weekend outfits for fall!

1. hoodie + sweatshirt skirt + sunglasses + tote bag + sneakers

weekend outfits

When it comes to mastering comfy yet stylish style, the secret is all in the fabric. If you can find classically polished items, like a skirt, but in a comfortable material, then you’re all set. A clothing item like a sweatshirt skirt adds a little bit of polish to your outfit and yet, it still feels like you’re wearing sweatpants! Perfect for running errands over the weekend on a fall day.

When it comes to footwear, stylish sneakers are the obvious choice. Sneakers can go with anything and everything, and when paired with skirts and dresses it looks casual yet stylish. Finish off this look with oversized sunglasses and a leather tote bag-perfect for your weekend shopping trip.

2. oversized blazer + hoodie + leather leggings + padded bag + clogs

weekend outfit ideas

Yes, a blazer can totally work in your weekend outfits for fall. The trick is to find a relaxed and oversized blazer in a simple fabric. Anything too stiff and structured doesn’t give off the comfy weekend vibes that you want! And an oversized fit is key, allowing you to layer hoodies and sweaters underneath since layering is a must not only for fall but to add that style to your outfit as well.

Finish off this look with clog-like shoes (which are coming back btw) and a padded shopper bag for an extra dimension to your outfit.

3. sweater dress + shopper bag + sunglasses + sneakers

fall weekend outfits

Nothing quite screams fall like a cozy sweater dress. A sweater dress is a must-have piece for every woman’s wardrobe. It’s the perfect way to look stylish and be comfortable all at the same time! Not only that, but a sweater dress is almost a one-and-done outfit.

You could layer on top of this, but you don’t need much to finish this look. Just add those stylish sneakers, sunglasses, and a bag, and you’re good to go!

4. oversized blazer + leather leggings + oversized hoodie + shopper bag + sneakers + baseball cap

fall weekend outfit ideas

Leather leggings are not only fall-appropriate, but the material adds that extra shine and dimension to an otherwise basic weekend outfit for fall. An oversized hoodie brings the comfy factor, while an oversized blazer pulls this look together and creates something stylish!

A baseball cap is a lifesaver for bad hair days or weekends when you don’t feel like putting much effort into your appearance or for the days that you ran out of dry shampoo. No one will be the wiser! Add stylish sneakers and a padded bag if you want your outfit to look a little bit trendy- then you’re all ready to head out the door.

5. oversized blazer + t-shirt dress + combat boots + tote bag

fall weekend outfit idea

A loose-fitting dress is always comfortable and when paired with that trusty oversized blazer, it’s stylish too. Combat boots, next to sneakers, are a perfect option for fall and they add a little bit of edge to your outfit.

When the weather starts to get a bit cooler, add some leggings or tights to this look and you’ll be good to go!

Now that you’re armed with comfy weekend outfits for fall, it’s time to make sure the rest of your fall wardrobe is in tip-top shape, by checking out this post on the best classic capsule wardrobe for fall!


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making mychicobsession.com a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.