This past fall, I launched a new series – What to Wear Where (W2WW). And since its launch, I’ve curated 13 looks for specific events. Today, I’m doing a What to Wear Where series roundup 2021 and announcing the most shopped look below. I hope you found this series valuable and were able to take some inspiration from some of the looks. I can’t wait to continue this series in the New Year. Below you’ll find links to each W2WW blog post. Happy New Year to you all!

What to Wear Where Series Roundup 2021

The Most Shopped W2WW Look: Chic Teacher

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This chic teacher outfit is all about incorporating pieces into your wardrobe that are appropriate for the classroom. While it’s warmer outside in most places when school starts, the weather quickly changes to fall-like weather. So I wanted to take into consideration that component too.

I started with cotton shirt and buttoned it all the way up. Then, cuffed the sleeves for a more sophisticated look. I layered a long sweater vest over the top to give the look a different texture and to add an additional layer for warmth. Because I’m more petite, I added a belt to my natural waist to give the look more structure.

I finished the look with knee-high boots and an oversized tote to carry all the essentials.

Fall Evening Wedding Guest

what to wear where roundup 2021

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This black dress features a tulip hem, giving the dress a high-low effect. This hemline works well if you’re a petite height, and won’t have to worry about the dress being too long in the front. It also has an elastic waistband with an adjustable tie, and features a button at the bust for added coverage and a secure feel. The sleeves and the back of the dress aren’t lined, but the top front and throughout the skirt are lined.

I paired the dress with a black leather sandal. They feature an ankle strap and have a four-inch heel. They’re a great staple pump to wear to weddings, work or other special occasions. I finished the look with a clutch, simple jewelry and a soft pink lip.

Fall Brunch with Friends

what to wear where roundup 2021

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This look features a gorgeous bell-sleeve floral dress. It’s such a unique detail, and gives the dress a feminine flare. The dress has a smocked detail on the top of the shoulders and hook-and-eye closure. It’s also double-lined, so it has great coverage throughout.

I paired it with knee-high snake-print boots. They feature a four-inch, covered heel and a small square toe. I finished the look with a felt hat and tote bag. I also added simple jewelry from David Yurman.

Fall Comfy Country Concert

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Concerts are a great excuse to wear fun and funky pieces from your wardrobe, like this fringe skirt. It’s a comfortable suede material with a little bit of spandex in it, so it moves with you. Instead of a fringe skirt, a suede or leather skirt would also work well. I paired a chunky, chenille sweater with the skirt and did a small front tuck. I added a western-inspired belt to help define the waistline and give the look structure. The metal on the belt also breaks up the monochromatic color palette.

Though these boots technically aren’t cowboy boots, they have a Western flare to them with the cutouts at the top and an exaggerated pointed toe. They’re a great option if you don’t want to invest in real cowboy boots, but want something with a country vibe.

Keeneland Fall Meet

what to wear where roundup 2021

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If you’re not familiar with what Keeneland Fall Meet is, it’s three weeks of horse races at Keeneland Race Course in Lexington. It has a rich history in my city, and it’s always so much fun to attend. 

Dressing in layers is best when attending Keeneland because the weather can vary from day to day. This affordable, cream sweater dress is a great option to wear. It’s not overly dressy and very comfortable to wear for a day at the races.

I paired the dress with a chic snap-front jacket. The Houndstooth print is a great fall pattern to wear, and will keep you warm on those chillier days. The fitted structure balances out the more forgiving fit of the sweater dress.

Cold Weather Game Day

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I like to dress in layers when going to a game outside. I started with a basic, long-sleeve t-shirt. It’s a great layering piece that acts as the base for your look. This one is affordable, soft and fits well. I sized up one in this shirt to a small.

I layered a puffer vest over my long sleeve tee. These are great to wear when it’s slightly chilly, but not cold enough to bundle up with a coat. I like to keep my tee and vest neutral, so I can pair a UK hat or other accessories.

I’m wearing my favorite leggings – the Lululemon Align 25″. You honestly can’t beat their quality and fit. They’ll last you a long time and you can style them multiple ways. The Align leggings have minimal seams and look streamlined for casual wear.

Fall Family Photos

what to wear where roundup 2021

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Leather and faux leather are popular fall fabrics. I love the deep brown color of this one. I’m wearing last year’s color, but this year they have a chocolate brown, which is really beautiful, and a bone white. The ruffle detail gives the skirt a feminine touch and fits true to size.

I paired it with an ivory off-the-shoulder thermal top. Tuck your sweater in for a more fitted silhouette.

Finally, I finished the look with these knee-high boots for a monochromatic pairing with the skirt. They have a nice high heel, so it will make your legs appear longer – which is great for photos! They also fit true to size. I kept my jewelry simple and chose a statement gold earring.

Trendy Thanksgiving Day

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For me, I love a good excuse to dress up. If your friends or family dress up a bit for Thanksgiving, this outfit is a great option. I started off with this gorgeous off-the-shoulder cream sweater that was a part of Caitlin Covington’s collection at Pink Lily. A neutral cream sweater is a great basic to have in your winter and fall wardrobe, and I like that it’s more fitted to tuck into pieces like skirts and skinny denim jeans. The off-the-shoulder element elevates the sweater and gives it a dressier, on-trend vibe. It runs true to size, and I’m wearing an XS.

I paired the sweater with a plaid mini skirt. I tucked the sweater into the skirt for a structured look. Plaid and houndstooth are great patterns to wear throughout the fall

Casual Thanksgiving Day

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Faux leather leggings are a great staple to style multiple ways throughout the fall and winter. They’re comfortable to wear and a great alternative to wearing denim or plain black leggings. The quality of this particular pair from Spanx is amazing and will last you for many seasons to come. 

They run a bit small so I sized up to a small. I get the petite length, but they also have regular and tall lengths. 

For a festive spin, I chose a fall-inspired graphic sweatshirt. Pink Lily has some really cute graphic sweatshirts and t-shirts. They’re perfect to dress up or dress down with sweatpants.

A sweatshirt and leggings will make all your comfort dreams come true on Thanksgiving. But to add a little sass to the look, I chose knee-high, snakeskin boots. Because the rest of the outfit features mostly solid colors, it’s nice to break it up with a fun print like snakeskin.

Winter Weekend Getaway

what to wear where roundup 2021

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I love versatilite outfits that can take you from day to night easily. It’s especially important to have these types of outfit options when you’re traveling.

This is my all time FAVORITE coat for many reasons. First, you can dress this coat up or down, so you can get a good price per wear out of it. Secondly, it looks so chic with the black fur and accentuated collar. It fits true to size.

A monochromatic outfit always looks so chic, whether it’s all black, blush, white etc. I started with an oversized sweater that’s legging friendly. I paired the sweater with these faux leather leggings by Commando. They have an extra-high control waist for a supportive yet comfortable feel. I sized up one to a small.

Office Holiday Party

what to wear where roundup 2021

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The holidays are the perfect time of year to break out your sequins, plaid, faux fur and pops of red! Holiday parties are so much fun to dress up for because you can wear all things sparkly.

This long sleeve sequin top in the color “disco” is the perfect mix of conservative meets holiday. Since it’s an office party, I love that it’s modest yet playful with the sequins. It has a straight cut fit and comes in another multi-color version too. It runs a tad big. I’m wearing my true size XS.

These black ankle pants can take you from day to night. Because the top has a straight shape, I paired a form-fitting ankle pant to balance the look. The ankle pants run true to size, and I’m wearing a 0SP. They’re a high-rise with a wrinkle-resistant material, which is perfect for traveling too. 

I finished the look with red pumps. Whether you’re wearing them to the office, a party or out to dinner, they make a festive statement.

Holiday Casual Wear

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I love being able to slow down and spend quality time with my family during the holidays. It’s generally cozy nights in having dinner together, baking cookies, wrapping gifts and all the fun things the holidays bring.

This comfy, cozy look centers around this gorgeous cashmere loungewear set from M.M. Lafleur. It features a zip-up hoodie jacket and jogger pants. It’s made of 100% cashmere, and I’m wearing the color chianti. It also comes in five other colors besides this deep burgundy that’s perfect for the fall and winter, especially around the holidays. I’m wearing my true size XS, so both pieces run true to size.

These ultra mini Ugg booties pair perfectly with this loungewear set. They’ll keep your feet warm on the coldest of days, and love that they don’t cover the jogger. It’s like you’re wearing a slip-on shoe, but winter style. The ultra mini Uggs come in a variety of colors. I have the chestnut suede, and they run true to size for me.

I suggest spraying your boots with a suede protector to prevent staining from water, salt or other winter elements. This keeps them looking brand new from season to season.

Holiday Dinner Date

what to wear where roundup 2021

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This would be a great look to wear out to dinner, to a play or musical or other festive holiday events for date night. The detailing of this dress is what sets it apart from many other knit dresses I’ve seen. The handkerchief hemline gives it a little sass and interest, and think the length is perfect for both petite and tall women. I’m wearing my true size XS, and fits very comfortably. It has a slim silhouette with a beautiful cutout on the upper back.

What I love most about this dress is its versatility. It can be dressed up for a date night or worn to the office. For an office look, pair a blazer with closed-toe pumps. You could also wear this to church, to a bridal/baby shower or to a rehearsal dinner.

Which look was your favorite from this series? Let me know in the comments below!

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XO Amanda

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