Thrift Meet Chic: 8 Tips for Styling 2024 Fall/Winter Outfits
Fall/Winter 2024/25 is shaping up to be all about blending timeless classics with just enough modern edge to keep things fresh and relevant. This trend mix makes it easy to style thrifted and vintage finds in a way that feels right on trend for 2024. Here’s a guide to 2024’s top styling trends that breathe new life into thrifted pieces, giving your wardrobe a chic, updated feel without spending a fortune.
I’m excited to share some key elements of my holiday e-book: TCTS Reclaimed Holiday Style Guide 2024, featuring a 90’s Connecticut homemaker inspired, resale-sourced Holiday Capsule Wardrobe and a “looks like $1M but it’s” Thrifted Christmas decor plan that will help you execute the season with style, comfort, and sustainability. These essentials prioritize resourcefulness, versatility, and ease, with just a touch of holiday sparkle—making it simple to transition from cozy gatherings to cocktail parties without missing a beat. In the words of my reclaimed hero Martha Stewart, Holiday 2024 is going to be “a very good thing.”
1. Chunky Loafers & Mary Jane Flats
Loafers and Mary Jane flats have made a strong comeback, pairing effortlessly with both dressy and casual looks. A sturdy, thrifted loafer or Mary Jane flat adds a touch of preppy nostalgia to any outfit.
Styling Tip: Pair loafers with cropped, wide-leg jeans to showcase both the shoe and your socks, which are a styling must this year. Thrift stores are gold mines for classic loafers, and Mary Janes can often be found in unique colors or finishes.
Modernize It: Add slouchy socks (extra points for burgundy!) for a cozy, layered effect.
LINks to shop
2. Dad Sneakers: New Balance 990 & Similar
Dad sneakers are here to stay, with the New Balance 990s and similar retro-inspired styles leading the pack. These chunky sneakers are perfect for adding a sporty, laid-back vibe to your look.
Styling Tip: Pair with vintage high-waisted jeans or cropped wide-leg pants to balance the bulk of the sneaker. For a casual twist, add a slouchy sweater or a holiday-themed knit.
Modernize It: Style dad sneakers with slouch socks in neutral tones or, if you’re feeling bold, burgundy. This look is comfortable yet fashion-forward, great for day-to-day wear.
LINks to shop
3. Birkenstock Clogs or Similar
The Birkenstock clog (or any clog with a sturdy, minimalist design) is a perfect find for thrift shoppers. These shoes pair well with everything from jeans to skirts and add an easygoing, boho feel.
Styling Tip: Pair clogs with cropped jeans to show off slouchy socks or layer them with patterned or burgundy socks for added color.
Modernize It: The relaxed silhouette of clogs pairs perfectly with wide-legged pants or slouchy joggers, creating an effortlessly chic look that’s both comfortable and stylish.
LINKS to shop
4. Burgundy Accessories
Burgundy is the color of the season, especially for legwear, bags, and belts. It adds warmth and richness to any outfit, and it’s a classic color that won’t go out of style.
Styling Tip: Add burgundy tights or socks to elevate a neutral outfit instantly. Look for vintage leather belts or handbags in this shade for an easy thrift store find.
Modernize It: Incorporate multiple burgundy elements in an outfit—such as socks and a bag—to create a coordinated, modern monochromatic look.
LINks to shop
5. Cropped Wide-Leg Jeans
Wide-leg jeans, especially cropped styles, are trending this year as they’re perfect for showing off statement socks and shoes. The silhouette adds a retro twist to modern outfits and makes for an easy thrifted find.
Styling Tip: Look for high-waisted, wide-leg jeans in a sturdy denim, and pair them with everything from loafers to dad sneakers to clogs.
Modernize It: Thrifted wide-leg jeans can be easily updated by pairing them with a simple, minimalist top, allowing the pants to be the focal point of the outfit.
LINks to shop
6. Denim-on-Denim Workwear Inspired Looks
Denim-on-denim is making a strong return, but with a twist: workwear-inspired styling. Think boxy denim jackets, straight-leg jeans, and sturdy silhouettes that feel rugged yet stylish.
Styling Tip: Pair a vintage denim jacket with jeans of a similar wash. Look for utilitarian details like pockets and hardware to add authenticity to the look.
Modernize It: To avoid the “Canadian tuxedo” effect, add a pop of color with burgundy accessories or a sleek pair of modern sneakers.
LINks to shop
7. Socks With Everything
2024 is all about socks as a key styling element. Whether with loafers, sneakers, or clogs, socks are now meant to be shown off rather than hidden.
Styling Tip: Choose slouchy or ribbed socks in colors like burgundy, cream, or charcoal, and style them over leggings or under cropped jeans.
Modernize It: Socks and tights in rich tones add a polished touch to any look, giving thrifted pieces a modern, curated vibe.
LINks to shop
8. Vintage Holiday Sweaters With Modern Basics
Holiday and winter-themed sweaters add a nostalgic charm to any outfit. This year, they’re being styled in unexpected ways, like layered over modern athleisure or paired with structured coats.
Styling Tip: Look for classic winter patterns like Fair Isle or duck motifs, and style the sweater over high-quality, minimalist joggers or leggings.
Modernize It: Top the look with a sleek wool coat (think Max Mara or similar styles) for a mix of playful and polished.
LINks to shop
Discover the Secrets to Spotting True Vintage!
The thrill of uncovering a genuine vintage treasure is like no other—but how can you tell if it’s the real deal? From deciphering labels to understanding materials and construction, learning these key details can help you identify authentic, high-quality pieces that stand the test of time. Download my FREE Vintage Identification Guide and become a pro at spotting vintage gems on your next thrifting adventure!
Embrace the thrifted life and reimagine classic pieces in a way that’s sustainable, stylish, and uniquely yours.
The beauty of these trends is that they make it easy to find key pieces at your local thrift store that still feel fresh and relevant. With a few modern styling techniques and on-trend pairings, you can transform these vintage finds into an effortlessly chic and current wardrobe.
This season, join me in reclaiming a holiday that’s more about presence and purpose than excess or Target hauls. With a thoughtful holiday capsule wardrobe and sustainably sourced decor, you’ll create an atmosphere that’s warm, stylish, and uniquely yours.
Love this and want more? Check out my 2024 Reclaimed Holiday Style Guide, where I’ dive deeper into styling tips, thrift shopping secrets, and holiday inspiration that’s full of heart.
Happy thrifting, and may your holidays be filled with joy, comfort, and creativity!
ready to craft your capsule?
Jenn coaches real women like you, both virtually and in person, to cement their personal style with a capsule wardrobe. Ready to discover the joy of dressing from a streamlined closet filled with clothes that fit, flatter and make you feel amazing every day?
I hope i’ve inspired you to set time aside to craft your Holiday Capsule Wardrobe and Decor. Take photos of your capsule and share it with the ladies and me on MappCraft | Tiny Closet, Tons of Style® Survival Guide private Facebook group!
Want more?
Schedule your free consultation call with me!
Download a FREE copy of my book: Clothes the Deal | The Guide for Transformative Personal Style
Also, If you haven’t already, join the fun on my private Facebook group MappCraft | Tiny Closet, Tons of Style® Survival Guide
xoxo Jenn