With the holidays on the horizon, sweater weather fashion, basic fall staples, and your holiday event calendar are in full swing! The hardest part is trying to decide what to wear where. You need chic pieces that easily pair and can be worn in multiple ways. The good news is Pretty Neutral was designed to make outfit styling simple. As your personal style coordinator, I’m taking you through some of my favorite Pretty Neutral fall pieces, perfect for every occasion, with my What to Where Wear: Pretty Neutral Fall Edition.

If you missed last week’s W2WW, I added a hint of spooky style to your Halloween night ensemble to dish out those wickedly delicious treats in with my What to Wear to Handout Halloween Candy look! 

What to Wear Where: Pretty Neutral Fall Edition

Stylish Sweaters

What to Wear Where: Pretty Neutral Fall Edition-sweater

Holiday Time with Family

Shop Better Together Sweater

The perfect cozy sweater is a fall must-have! It’s a great basic piece to add to any wardrobe and offers endless styling possibilities from denim to trousers to skirts and leggings. This Better Together Sweater has just the right amount of stylish fall vibes thanks to its oversized fit and braided cable knit detailing. When it comes to holiday time with the family, consider this fresh fall look your new go-to! For size reference, I’m normally an xs and am wearing a small.

What to Wear Where: Pretty Neutral Fall Edition-sweater

Lunch with Friends

Shop Happy Half Zip Up Sweater

While we’re on the topic of sweaters, how gorgeous is this pink half zip-up! The ruffle print fabric against the faux fur bodice adds the perfect feminine touch to your everyday wear while keeping you ultra warm! It’s versatile enough to showcase on its own, as outerwear when lunching with friends or can easily be worn underneath your winter jacket as the temperatures start to dip. Pair with your favorite denim jeans and booties for a casually cozy look! The sweater runs true to size, wearing a size small.

Fashionable Fall Workwear

What to Wear Where: Pretty Neutral Fall Edition-cardigan

Work from Home Zoom Meeting

Shop Oversized Contrast Cardi

From holiday to casual to workwear, sweaters are the stylish solution to all your fall wardrobe needs. Next, are a few fabulous work-ready pieces that offer the perfect elegant style, whether you are in the office or behind a camera!

Is there anything better than a classically chic cardigan? This sophisticated sweater offers effortless elevated style with its oversized fit and contrasting gold buttons. To keep things casual, pair with denim jeans or take this look office ready with high-waisted trousers. I’m wearing a size small, and this piece has an oversized fit.

Sophisticated Fall Workwear

Shop Desk to Dinner Neck Tie Top High Waist Wide Leg Pant Buttoned Up Sweater Cardigan

I’m taking your workwear style from Zoom to the boardroom with these two easy and sophisticated looks. Combine unapologetically cozy trousers with a beautifully draped blouse or quintessential cardigan, for guaranteed style from 9 to 5, as well as after hours! Pieces run true to size. Wearing a size small. For a cozier fit, size up one in the Cardigan. The pants have a 30″ inseam, and for reference, I’m 5’2″ and wearing 5-inch heels.

Weekend Wear Staples


Weekend Activities with the Kids

Shop Gotta Have It Hot Pink Sherpa

Weekends are for all things kids activities which likely means you’re headed outdoors. This ultra-soft sherpa jacket is the perfect thing to keep you toasty warm while adding just the right amount of fashionable flair to your look! Standout with style as you cheer your littles on! This jacket runs true to size (wearing a size small), offers a snap-up front with zip pockets, and has plenty of room for additional layers underneath. Throw it on over a long-sleeve tee and trendy kicks for a classic casual look.

What to Wear Where: Pretty Neutral Fall Edition-sweater

Weekend Errands

Shop Side Slit Tunic Sweater

Whether you’re brunching, shopping, or crossing off the rest of your to-dos, weekends can be spent running all over the place! But just because you’re out and about doesn’t mean you can’t run your errands in style! This tunic will keep you effortlessly chic while casually comfortable! Its beautiful balloon sleeves, drop shoulder frame, and relaxed bodice creates an oversized fit perfect for a trendy front tuck but long enough to rock a pair of edgy faux leather leggings! I’m wearing a size small.

Quilted Coat

Sunday Best

Shop Ruffle Detailed Quilted Coat

Wearing your Sunday best has taken on a whole new meaning, thanks to fashion-forward outwear! This midi-length quilted puffer coat is sure to keep you warm and classy thanks to its stylishly chic look. It offers the sweetest ruffle hem, functional pockets, and a self-tying belt to accentuate the waistline. Wear over your favorite elegant dress for the perfect sophisticated style. This coat fits true to size, and I’m wearing a small.

Thanksgiving Day Inspiration

Timeless Holiday Look

Shop Pretty Poplin Dress & Quilted Jacket

You might recall my obsession with white dresses from LTKCON when I packed not one but three! They’re a personal favorite and for good reason. It’s stylish, easy to wear, and perfect for any occasion! There’s just something so dreamy about a crisp white cotton dress and its effortless tiered layering for added whimsical charm. This flattering piece is neutral enough to be dressed up with or down for versatile styling options. I paired it with knee-high boots and this beautiful oversized quilted jacket to complete this Thanksgiving day-ready look. The jacket pairs well over winter sweaters and dresses for added warmth. I’m wearing an S/M. The dress fits true to size, and I’m in a small.

Maxi dress

Feeling Thankful Floral Maxi

Keep Checking Back Restocking Soon!

I wore this gorgeous floral maxi dress to Keeneland a few weeks ago and it’s truly stunning! It’s not only comfortable but wears well with knee-high boots and was warm enough in low 60-degree temps, without a jacket. It would make the perfect look for Thanksgiving!! It’s currently sold-out but keep checking back because it will be restocked soon! Dress runs true to size and I’m wearing a small (normally an xs (5’2″, 32). There is extra room in the bust but the top snaps keeps everything in place.

What’s your favorite What to Wear Where: Pretty Neutral Fall Edition look? Let me know in the comments below!

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XO Amanda