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The Lillie Bag

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January 13, 2025

Winter to Valentine’s Day Looks You’ll Adore

Hi, friends! With winter in full swing and Valentine’s Day just around the corner, it’s the perfect time to refresh your wardrobe with versatile looks that transition seamlessly from cozy winter days to heart-filled celebrations. I’ve pulled together some of my favorite outfits to inspire you, whether you’re heading out for a Galentine’s Day brunch or staying in for a cozy night.

WINTER STAPLES: sweaters

Free People Sweater Love: This sweater has been on repeat for me! It’s the perfect mix of cozy and chic, and I love pairing it with leggings or jeans for that effortless vibe. And it’s currently on sale!

Amazon Tunic Sweater: This tunic sweater is such a steal and come in so many cute colors! I love styling them with faux leather leggings or layering them under one of my favorite coats.

WINTER STAPLES: COATS

Screenshot
Screenshot

VALENTINE’S DAY LOOKS

Now, let’s get into the Valentine’s Day vibe! No matter how you’re celebrating, I’ve got you covered! Stay-In Cozy Chic: If your Valentine’s plans involve staying in, go for cozy and cute. I’m obsessed with pairing soft loungewear sets or oversized tunic sweaters with fuzzy slippers and a fun scrunchie for a laid-back but lovable vibe.

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Screenshot
Screenshot
Screenshot

I hope these looks inspire you to feel your best this season! Whether you’re bundling up for the winter chill or adding a pop of pink for Valentine’s Day, there’s something so special about dressing for the moment. Thank you for being here—it means so much to me to share these moments and ideas with you!

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Hi, I’m Lauren

Hi, I’m Lauren

Lauren

I'm a Mom, Hair Stylist, and Wife who loves styling the layers of life! From my style to yours and all affordable things in between, I'm so glad you're here with me! Always comfy, sometimes cute, and will work for wine! Cheers to my take on "Styling the Layers of Life!"

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Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

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From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

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From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

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From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

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Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

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Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼 Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
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Work appropriate. Weekend approved. 🤌🏼🍂🏈 Comment STYLE to shop or head to bio! ✨ The sweater that works with heels AND your team colors!👀 Comes in the best neutrals too, because obviously I need options! Ok what’s your team colors bc none of ours are the same in this house! I’m going from red to blue & back again🏐🫠! Must be following for messages to send 💌! Fall outfit, fall style, sweater, jeans, suede heels, brown, sports mom, style over 40, women’s fashion, affordable style, heels, workwear, Chicago, weekend, eat, ate, easy outfits, ootd, fall tops, workwear style
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Amazon did not come to play with the fall shoes 👀🍂 Comment SHOES to shop or head to bio! 

7 pairs that look WAY more expensive than they are + I’m already calling a few of these the shoes of the season! 🤌🏼 not to mention my store front agrees💯🙋‍♀️ one of my go to brands for comfort and quality! 

Must be following for messages to send 💌

Fall shoes, fall style, fall boots, workwear, fall 2026, Amazon fashion, affordable fashion, looks for less, Chicago, weekend, style over 40, women’s fashion, eat, ate, suede, mules, fall outfits, @coutgo.official
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Amazon did not come to play with the fall shoes 👀🍂 Comment SHOES to shop or head to bio! 7 pairs that look WAY more expensive than they are + I’m already calling a few of these the shoes of the season! 🤌🏼 not to mention my store front agrees💯🙋‍♀️ one of my go to brands for comfort and quality! Must be following for messages to send 💌 Fall shoes, fall style, fall boots, workwear, fall 2026, Amazon fashion, affordable fashion, looks for less, Chicago, weekend, style over 40, women’s fashion, eat, ate, suede, mules, fall outfits, @coutgo.official
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Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
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Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

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Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼 Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! 
From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼

Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
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Oh these are GOOD good 💯🤏🏼👀! Looks that absolutely ate this week. Comment STYLE to shop! From the viral pants I’ve styled 100 ways to the 15 dollar fall find you need + sneakers that make me happy 😂 Which one wins?!🤏🏼 Fall style, fall outfits, sports mom, style over 40, women’s fashion, Chicago, weekend, denim, baggy jeans, fall 2026, eat, ate, jacket, outerwear, workwear, fall outfit, travel look, sneakers, suede bag, designer bag, fall trends
2 days ago
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What do we think😍!? I personally love them AND found them in stock! Comment STYLE to shop before they are gone or head to bio! 🤏🏼💯

Now to keep my kids from taking them! Maybe put them aside for Christmas! 👀

Fall style, fall shoes, Ugg, mules, clog, women’s fashion, style over 40, new arrival, fall 2026, trending now, Chicago, weekend, eat, ate, mom style, casual outfits, fall trends, fall 2026,
•
Follow
What do we think😍!? I personally love them AND found them in stock! Comment STYLE to shop before they are gone or head to bio! 🤏🏼💯 Now to keep my kids from taking them! Maybe put them aside for Christmas! 👀 Fall style, fall shoes, Ugg, mules, clog, women’s fashion, style over 40, new arrival, fall 2026, trending now, Chicago, weekend, eat, ate, mom style, casual outfits, fall trends, fall 2026,
4 days ago
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2/6
Work appropriate. Weekend approved. 🤌🏼🍂🏈
Comment STYLE to shop or head to bio! ✨

The sweater that works with heels AND your team colors!👀 Comes in the best neutrals too, because obviously I need options! Ok what’s your team colors bc none of ours are the same in this house! I’m going from red to blue & back again🏐🫠! 

Must be following for messages to send 💌! 

Fall outfit, fall style, sweater, jeans, suede heels, brown, sports mom, style over 40, women’s fashion, affordable style, heels, workwear, Chicago, weekend, eat, ate, easy outfits, ootd, fall tops, workwear style
•
Follow
Work appropriate. Weekend approved. 🤌🏼🍂🏈 Comment STYLE to shop or head to bio! ✨ The sweater that works with heels AND your team colors!👀 Comes in the best neutrals too, because obviously I need options! Ok what’s your team colors bc none of ours are the same in this house! I’m going from red to blue & back again🏐🫠! Must be following for messages to send 💌! Fall outfit, fall style, sweater, jeans, suede heels, brown, sports mom, style over 40, women’s fashion, affordable style, heels, workwear, Chicago, weekend, eat, ate, easy outfits, ootd, fall tops, workwear style
5 days ago
View on Instagram |
3/6
Amazon did not come to play with the fall shoes 👀🍂 Comment SHOES to shop or head to bio! 

7 pairs that look WAY more expensive than they are + I’m already calling a few of these the shoes of the season! 🤌🏼 not to mention my store front agrees💯🙋‍♀️ one of my go to brands for comfort and quality! 

Must be following for messages to send 💌

Fall shoes, fall style, fall boots, workwear, fall 2026, Amazon fashion, affordable fashion, looks for less, Chicago, weekend, style over 40, women’s fashion, eat, ate, suede, mules, fall outfits, @coutgo.official
•
Follow
Amazon did not come to play with the fall shoes 👀🍂 Comment SHOES to shop or head to bio! 7 pairs that look WAY more expensive than they are + I’m already calling a few of these the shoes of the season! 🤌🏼 not to mention my store front agrees💯🙋‍♀️ one of my go to brands for comfort and quality! Must be following for messages to send 💌 Fall shoes, fall style, fall boots, workwear, fall 2026, Amazon fashion, affordable fashion, looks for less, Chicago, weekend, style over 40, women’s fashion, eat, ate, suede, mules, fall outfits, @coutgo.official
6 days ago
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The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️

The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎

must be following for messages to send💌

Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
•
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The weekly winners 👀 & apparently we’re in our sideline style era now too 🏐🏈😂! Comment SHOP to shop or head to bio! ❤️ The jeans I cannot stop wearing, the pants that basically took over my storefront, THE internet jacket in new colors + a few game day finds that you will love this season⚽️🏈🏐🤎 must be following for messages to send💌 Fall style, fall outfits, sports mom, volleyball, game day, fall 2026, weekend, Chicago, eat, ate, women’s fashion, style over 40, travel look, workwear, jeans, pants, fall fashion, casual outfits, sports, sideline outfits, sneakers, denim,
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when you don’t know what to wear- let it be this! Most clicked on the store front lately🤏🏼🤌🏼💯 Comment STYLE for a DM to shop or in bio! 

Must be following for messages to send💌

Fall style, women’s fashion, sports mom, casual, fall outfits, casual look, travel style, weekend, style over 40, fall 2026, Chicago, sweater, pants, mules, outfit idea, affordable style
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when you don’t know what to wear- let it be this! Most clicked on the store front lately🤏🏼🤌🏼💯 Comment STYLE for a DM to shop or in bio! Must be following for messages to send💌 Fall style, women’s fashion, sports mom, casual, fall outfits, casual look, travel style, weekend, style over 40, fall 2026, Chicago, sweater, pants, mules, outfit idea, affordable style
1 week ago
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6/6
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