As the leaves start their graceful descent and the air gets that distinctive crisp feel, I find myself standing in front of my wardrobe, contemplating the perfect outfits that’ll carry me through this tricky transitional season. Having navigated countless fall-to-winter wardrobe switches in my career as a style editor, I’ve mastered the art of creating looks that are both practical and Pinterest-worthy. Today, I’m excited to share my favorite transition pieces that’ll keep you looking polished while staying cozy as the temperature drops.
1. Sporty Chic Black Set with Blazer and Sneakers Combo
There’s something magical about throwing on a perfectly tailored blazer over activewear – it’s like telling the world “Yes, I can do both.” I’ve discovered that pairing a black matching set (think luxe stretchy material) with a structured blazer creates an unexpected harmony. The key is choosing a blazer with subtle shoulder padding and a slightly oversized fit.
What I’m wearing:
- High-waisted black leggings with subtle compression
- Matching black cropped tank with built-in support
- Oversized charcoal blazer (size up for the perfect slouch)
- White leather sneakers
- Gold-toned minimal jewelry
Styling Tips:
- Roll up the blazer sleeves twice for a relaxed vibe
- Add a delicate gold necklace to elevate the athletic pieces
- Keep hair sleek in a low bun or ponytail
- Choose sneakers without obvious branding for a cleaner look
RECREATE THIS LOOK
2. Cozy Plaid Shacket with Sweatpants Street Style Look
On those days when the morning starts chilly but promises afternoon warmth, I reach for my trusty plaid shacket. It’s become my absolute go-to for those “what do I wear?” moments. The beauty of this piece lies in its versatility – it’s essentially a shirt-jacket hybrid that works overtime to keep you looking put together.
What I’m wearing:
- Oversized plaid shacket in rust and cream
- High-quality grey sweatpants (look for tapered legs)
- White fitted turtleneck
- Chunky cream socks
- Platform sneakers
Styling Tips:
- Choose sweatpants in a premium cotton blend for structure
- Tuck the turtleneck in front for shape
- Push up the shacket sleeves to show the turtleneck underneath
- Add minimal gold jewelry for polish
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3. Bold Red Sweater Vest with Distressed Denim Casual Style
When I first tried styling a sweater vest, I was skeptical. Now? It’s my secret weapon for creating dimension without bulk. The key to making this preppy piece feel modern is all in the proportions and how you layer it.
What I’m wearing:
- Chunky knit red sweater vest
- Oversized white button-down shirt
- High-waisted distressed straight-leg jeans
- White ankle boots
- Pearl ear cuffs
Styling Tips:
- Leave the button-down untucked for movement
- Roll sleeves up to the elbow
- Choose a vest that hits at hip length
- Add delicate jewelry to balance the bold color
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4. Oversized Flannel with Leggings and Clogs Comfort Look
There’s something about an oversized flannel that just feels like a warm hug. I’ve found that the key to making this casual piece look intentional is all in the accessories and how you style it.
What I’m wearing:
- Buffalo check flannel in navy and forest green
- High-quality black leggings with pocket details
- Black fitted tank top
- Shearling-lined clogs
- Leather crossbody bag
Styling Tips:
- Half-tuck the flannel for shape
- Choose leggings with subtle compression
- Add gold-toned hair clips for polish
- Layer delicate necklaces
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5. Preppy Layered Orange Sweater with Baseball Cap Style
Who says preppy can’t be cool? This look has become my weekend favorite, perfect for everything from farmers’ market runs to casual coffee dates.
What I’m wearing:
- Burnt orange cable knit sweater
- White collared shirt
- High-waisted straight-leg jeans
- Classic baseball cap in navy
- White leather sneakers
Styling Tips:
- Let the collar and cuffs peek out perfectly
- Choose a sweater with slight oversizing
- Cuff jeans once or twice
- Keep makeup natural and glowy
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6. Sunset Athleisure with Brown Cardigan and Nike Sneakers
The athleisure trend isn’t going anywhere, and I’ve found ways to make it feel fresh and seasonal. This combination has gotten me more compliments than any other casual look.
What I’m wearing:
- Chocolate brown longline cardigan
- Matching mauve workout set
- Nike Air Max sneakers in cream
- Gold-toned chain necklace
- Scrunchie in matching brown
Styling Tips:
- Belt the cardigan for shape
- Choose a workout set in a ribbed material
- Add minimal jewelry
- Keep hair casual but neat
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7. Oversized Denim Shirt with Black Leggings and Mules
The denim shirt is my ultimate transitional piece. It’s like a chameleon – dress it up, dress it down, layer it, tie it – the possibilities are endless.
What I’m wearing:
- Light wash oversized denim shirt
- Premium black leggings
- Black leather mules
- Canvas tote bag
- Layered gold necklaces
Styling Tips:
- Roll sleeves precisely
- Add a belt for definition
- Choose mules with architectural details
- Layer delicate jewelry
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8. Olive Quilted Coat with Wide-Leg Jeans Coffee Run Look
This outfit has become my signature look for those crisp morning coffee runs. The mix of casual and polished elements makes it perfect for running into anyone from your boss to your ex.
What I’m wearing:
- Olive green quilted coat
- Cream turtleneck sweater
- High-waisted wide-leg jeans
- Leather ankle boots
- Structured leather bag
Styling Tips:
- Leave coat unbuttoned for movement
- Tuck sweater completely
- Choose boots with a slight heel
- Add minimal gold jewelry
RECREATE THIS LOOK
9. Fall Cardigan with Light Wash Denim Casual Weekend Style
This combination works every single time. It’s my foolproof formula for looking put together while feeling like I’m wrapped in a blanket.
What I’m wearing:
- Chunky knit cardigan in camel
- White fitted t-shirt
- Light wash mom jeans
- White leather sneakers
- Canvas tote bag
Styling Tips:
- Leave cardigan unbuttoned
- Front tuck the t-shirt
- Cuff jeans once
- Add delicate jewelry
RECREATE THIS LOOK
10. Cream Puffer Jacket with Dark Denim Winter Ready Outfit
As temperatures really start to drop, this outfit keeps me looking chic while staying warm. The key is choosing a puffer that’s fitted rather than overly bulky.
What I’m wearing:
- Cream fitted puffer jacket
- Black turtleneck sweater
- Dark wash straight-leg jeans
- Combat boots
- Leather crossbody bag
Styling Tips:
- Choose a puffer with waist definition
- Tuck sweater completely
- Add gold-toned accessories
- Keep makeup warm-toned
RECREATE THIS LOOK
Frequently Asked Questions
Q: How can I make these outfits work for a more corporate environment?
A: Layer blazers over the looks, swap sneakers for loafers or pumps, and choose darker wash denim. The key is keeping the base outfit but elevating the accessories and outer layers.
Q: What if I live in a warmer climate?
A: Choose lighter materials like cotton instead of wool, opt for shorter sleeves, and focus on layering pieces that can be easily removed. The shacket and cardigan looks work particularly well for mild winters.
Q: How can I make these outfits more budget-friendly?
A: Focus on investing in quality basics like jeans and boots, then save on trend pieces like the shacket or sweater vest. Thrift stores often have great oversized flannel shirts and vintage denim.
Q: What size should I choose for the oversized pieces?
A: Generally, go up one size for a modern oversized look. For pieces like the flannel or shacket, you might want to go up two sizes depending on your desired fit. Always check the shoulder seams – they should sit just slightly past your natural shoulder.
Q: How do you keep oversized pieces from looking sloppy?
A: The key is balance – pair oversized tops with fitted bottoms or vice versa. Always make sure one element of your outfit is structured, and add refined accessories like delicate jewelry or a structured bag.
These outfits have become my go-to formulas for navigating the tricky fall-to-winter transition with style. Remember, the best outfit is one that makes you feel confident and comfortable. Mix and match these ideas to create your own signature looks that work for your lifestyle and personal style.
