Fall Wardrobe Reset: 5 Cozy Chic Pieces Every Messy Woman Needs

If you are like me, you are super excited for October, fall, and spooky season, but thanks to global warming or Mother Nature being in a mood (just like me), we never know what to expect in fall. We know it will get chilly, but then out of nowhere we’ll have a 70+ degree day and it will mess up our fall vibe and, most of all, our outfits.

Which is why instead of resetting our closet and packing your summer clothes in the attic or storage, I want to suggest 5 cozy pieces that you can use during this transition that will make you feel fall-ready. They can be layered for brisk mornings and peeled off when you feel like melting later in the day.

You don’t need to reinvent the wheel when it comes to trends. Be comfortable, look good, and keep it simple. Here are 5 pieces of clothing that work perfectly during this fall reset:

1. The Oversized Vest
2. The Strappy Dress
3. The Pants That Work With Everything
4. The Sweater for All Weather
5. The All-Weather Shoe

Wardrobe Reset: 5 Pieces to Save Your Fall Vibe

As much as we love to spend money (aka messy shopaholics), we have to pretend to be responsible sometimes and make our significant other believe we haven’t bought new clothes.😬

Unless, of course, you thrift or buy from resellers like Poshmark or Whatnot, in that case, shop away because you definitely got a great deal.🤑

I digress. You don’t need to reinvent your whole closet. These five pieces are like your ride-or-die besties, always there, always working, no matter if it’s 50° or 75°.

Make sure that when you shop, you get these pieces in neutral colors or colors that align with your color palette so you can wear them often without struggling with how to style them.

1. The Oversized Vest: A Fall Outfit Hero for Messy Women

Layer it over a turtleneck on chilly mornings, a button-down shirt for those in-between days, or throw it on with a tee when it’s warmer.

Bonus: It makes you look like you planned your outfit, even if you were running out the door with baby spit-up on your sleeve or after an extra-lengthy happy hour with an awful hangover.

Pro Tip: Buy it one size bigger so the look stays oversized, and no matter how many layers you wear underneath or on top it still looks fab!

2. The Strappy Dress: Cozy Transition Staple You Already Own

Yes, your summer dress still works in fall. Throw a chunky cardigan, oversized blazer, bomber jacket, or leather jacket on top, add boots, and suddenly it screams “cozy but make it stylish.” No need to say goodbye to it yet.

Bonus: The jacket you choose sets the vibe. Leather for baddie, bomber for casual, cardigan for cozy. You can also layer on top or under the dress with lace, a mesh top, or a tee.
Pro Tip: Wear a cropped jacket or make sure it hits your waist so you can create a visual hourglass. A belt can also help with this.

3. The Pants That Work With Everything (Yes, Even Your Messy Days)

Wide-leg trousers or straight-leg jeans = lifesavers. Pair them with sneakers and a tee for errands, or boots and a lightweight sweater for “I’m pretending I have my life together” mod

Bonus: Free People makes awesome denim trousers that cover this “work with everything” category, they are light, flowy and comfortable for any weather.

Pro Tip: Boot Cut jeans are trending this fall and never go out of style, but choose the pant leg that makes you feel comfortable and works with your body type

4. The Sweater for All Weather: Your Emotional Support Knit

That mid-weight knit you can wear alone, layer under a coat, or tie around your shoulders when it’s 72 ddegrees, but you need to look like fall. Basically, your sweater is your emotional support blanket disguised as fashion.

Bonus: Men’s sweaters are underrated. They are comfy, oversized, and perfect for this vibe.
Pro Tip: H&M has awesome men’s sweaters that look great for a put-together, comfortable look or just steal it from your significant other.

5. The All-Weather Shoe: Stomp Into Fall Like a Badass

Ankle boots are the MVP, not too hot, not too cold. They go with almost everything depending on the type of boot.

Bonus: On warmer days, swap them for loafers or sneakers, but always have that one pair of boots that make you feel like you’re stomping through life like a badass.

Pro Tip: Add fun socks to give your look some pizzazz. In summer wear mesh socks with fun patterns, and for chilly days wear wool socks or ruffle socks to zhuzh up those boots.

✨ Messy Woman Routine: 3 Steps to Fall Outfit Sanity

Look, I love fashion, but I also love sleep… and scrolling… and pretending I didn’t hear my husband go to work at 6AM. So this little routine is my sanity saver when I want to look put together without thinking too hard. Hopefully it can help you too:

1. Check the Weather First → Because Mother Nature is moody. Knowing if it’s 50° or 75° means no sweaty pits or goosebumps in a sundress. You’ll be ready for anything.
2. Plan One Outfit Ahead → Lay out your vest, pants, or sweater the night before. Make sure to have a backup layer that you can take on or off just in case. (Bonus points if it’s clean and not living in the laundry pile).
3. Add a Wildcard Piece → Funky socks, a plaid scarf, bold lipstick, a spiky headband, one thing that makes you smile when you catch yourself in the mirror. The plan is to make this outfit yours by adding touches of your personality. That’s the secret sauce.

👉 That’s it. These three little moves will make you feel like you’ve got your life together (even if you don’t).22

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✨ Messy Woman Affirmations: Cozy, Chic & Confident

Feeling good is not just about the clothes and accessories, it’s the attitude you put into the outfit. It’s about believing in yourself and your outfit creation. Try these affirmations in front of the mirror while getting ready or after you’re done looking like a Badass Fashionista, and watch the magic happen:

• “I look good in whatever I choose, because I chose it.”
• “My mess is my vibe, not my flaw.”
• “Getting dressed is my daily act of self-love and self-expression.”
• “I dress for me, not for perfection.”
• “Every outfit I wear is a reflection of my messy, magical self.”
• “I am awesome, no matter how messy I am.”

Now that you’re inspired and have found the pieces from summer you can keep, or shop for your fall transition pieces, subscribe to the newsletter (Letters from the Mess goes out every other Thursday) for more tips to help you find your Badass in the Mess of life. And don’t forget to grab my freebie, 21 Days of Messy Pages.

Yup, some of these links are affiliate links. If you grab something, I might make a small commission no extra cost to you, just helping a messy mama build her dream biz. You’re the real MVP.