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My Dream Fall Wardrobe
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items I blame What Not to Wear for this list. I grew up watching Stacey London and Clinton Kelly transform wardrobes, and I still half expect them to show up one day and tell me it’s time for an overhaul. If they did, these are the pieces I’d be adding to ...
Sections
8
Dresses
Tops & Sweaters
Denim
Bottoms
Layers & Jackets
Shoes
Dresses
The dream fall dress lineup is all about pieces that can carry you from late summer into actual sweater weather.
A little romantic without feeling overly sweet. This is exactly the kind of mini I’d wear with boots, a cardigan and a very fall coffee in hand.
Madewell The Melody Smocked Minidress
Denim dresses are one of my favourite ways to make an outfit feel pulled together without actually trying very hard. This one has major everyday fall potential.
Madewell Denim Boxy Shirtdress
For those early fall days when it still feels like summer in the afternoon but you’re mentally ready for September. Add boots and a jacket and I’m sold.
Rails Anastasia Shirred Sleeveless Maxi Dress
This is probably the most obviously fall piece of the bunch, and I love it. Plaid, pleats and a midi length feels like the perfect excuse to go apple picking.
Julia Jordan Plaid Pleated Midi Dress
A little more playful than the classic denim shirtdress, and the flared skirt makes this one feel especially cute with sneakers or ankle boots.
Women's Denim blue Denim Dress with Flared Skirt
The kind of knit dress that feels effortless but still looks like you actually got dressed. I’d pair this with tall boots and a jacket once it gets chilly.
Reformation Jamen Off Shoulder Knit Midi Dress
Tops & Sweaters
These are the pieces that make getting dressed in fall so easy.
Wear it on its own now, layer it over a tee later. The versatility alone earns it a spot.
Madewell Button Front Sleeveless Cardigan
The kind of basic you’ll reach for several times a week without even thinking about it.
Madewell The Perfect Crewneck Tee
A slightly more fitted take on the everyday white tee. Perfect for layering under jackets and cardigans.
Madewell The Perfect Crewneck Baby Tee
The perfect striped tee is a wardrobe staple, and this one has that effortless “I’ve owned it forever” look.
Barbour Otterburn Stripe T Shirt
For those dinners or date nights where you want to look a little elevated without giving up knitwear season.
Reformation Iris One-Shoulder Knit Top
The rich burgundy colour instantly makes every outfit feel like fall, even if you’re still wearing denim shorts.
Women's Burgundy Short-Sleeved Fine-Knit Cardigan
Soft, feminine and easy to style. This feels like the sweater version of your favourite neutral tee.
Women's Brown Cap-Sleeved Pointelle-Knit Cardigan
A beautiful elevated knit that proves neutral sweaters never have to be boring.
FRAME The Gathered Honeycomb Cashmere Sweater
A classic gingham button-up is one of those pieces that somehow works for everything from workdays to pumpkin patches.
Rails Josephine Gingham Button-Up Shirt
The oversized stripes and mockneck give this sweater that perfectly relaxed, weekend-in-the-fall feel.
PARKE Vintage Stripe Sweatshirt
The sweater you’ll throw over your shoulders at the farmers’ market and actually end up wearing all day.
Free People Classic Stripe Sweatshirt
Cozy without feeling bulky. This is exactly the kind of sweater that makes crisp mornings something to look forward to.
Pistola Nadya Alpaca Blend Boxy Polo Sweater
One of my favourite affordable sweaters. It looks just as good with leggings as it does with denim and tall boots.
Seaside Cotton Shaker Tunic Sweater
The iconic bear sweater will never not feel charming. It’s classic, cozy and somehow always comes back every fall.
Polo Ralph Lauren Cotton Bear Long Sleeve Crew Neck Pullover
Denim
A good pair of jeans can completely change an outfit.
Every wardrobe needs a great pair of black denim, and this wide-leg silhouette feels modern without trying too hard.
Levi's Ribcage Wide Leg Jeans
Comfort and structure rarely go hand in hand, but these promise both. Exactly what I want in an everyday pair of jeans.
Reformation Bex Super Stretch High Rise Wide Leg Jeans
A clean, classic crop that works just as well with loafers as it does with ankle boots.
SLVRLAKE Grace Crop Jeans
The kind of effortless denim that instantly makes a simple sweater and sneakers look intentional.
AGOLDE High Rise Wide Leg Ren Jeans
A dramatic wide leg that still feels timeless. These would be beautiful with a fitted knit and a belt.
Good American Good Waist Palazzo Jeans
The perfect vintage-inspired pair that somehow manages to look relaxed and polished at the same time.
AGOLDE Lana High Rise Vintage Straight Jeans
A great alternative to wide-leg denim when I want something a little more classic without sacrificing comfort.
SLVRLAKE Virginia Tapered Leg Jeans
The kind of piece that makes getting dressed feel fun again. I’d throw these on with a striped tee and sneakers all fall long.
Free People Ziggy Denim Overalls
Bottoms
These are the pieces I’d build the rest of my wardrobe around.
A rich burgundy skirt instantly makes any outfit feel like fall. I’d wear this with boots, a fitted cardigan and a long wool coat.
Women's Burgundy Midi Skirt
An easy, elevated skirt that works just as well with a simple tee as it does with a chunky knit.
RAILS Romina Skirt
Relaxed tailoring is one of my favourite trends. These look polished without sacrificing comfort.
AG Century Cinched Pants
The perfect combination of relaxed and refined. These are the kind of pants I’d reach for when I want to be comfortable but still look put together.
Women's Dark brown Pleated Drawstring Pants
Layers & Jackets
Fall is really all about the layers. These are the jackets and outerwear I’d reach for every year because they feel timeless, practical and somehow make every outfit look better.
Perfect for crisp mornings, weekend walks and every coffee run once the temperatures start dropping.
Patagonia Women's Retro Pile Fleece Vest
A lightweight vest is one of my favourite layering pieces because it’s practical without feeling bulky.
Patagonia Women's Down Sweater™ Insulated Vest
If there was one jacket that defined my dream fall wardrobe, it would probably be this. The corduroy collar makes it feel perfectly classic.
Women's Jacket with Corduroy Collar
This has that timeless, outdoorsy feel that never goes out of style. I can already picture it at the apple orchard.
Patagonia Women's Point Reyes Cotton Canvas Coat
A quilted jacket is one of those pieces that somehow makes every fall outfit feel instantly cozier.
Women's THERMOLITE® Quilted Jacket
The rich cognac colour makes this feel softer and more versatile than a traditional black leather jacket.
Women's Leather Jacket
The kind of casual layer I’d throw on with denim, leggings or dresses without giving it a second thought.
Madewell Denim Chore Jacket
The contrast corduroy collar completely won me over. This is classic fall style at its best.
Madewell Denim Rancher Jacket
A lightweight trench is the perfect layer for those in-between days when it’s chilly in the morning and warm by lunch.
Women's Short Tie-Belt Trench Coat
Every dream wardrobe deserves one beautiful wool coat that instantly elevates even the simplest outfit.
Longline Wool Blend Reefer Coat - Lauren Ralph Lauren
The jacket I’d keep by the door all season long. Warm, lightweight and one of those pieces I’d reach for almost every day.
Patagonia Women's Down Sweater™ Insulated Jacket
Shoes
A great wardrobe starts from the ground up. These are the shoes I’d actually wear on repeat all fall, from everyday sneakers to boots I’ll still love years from now.
Whether it’s the cognac or chocolate brown, these feel like the definition of effortless fall style. I’d wear them from September right through November.
Birkenstock Boston Big Buckle Clog (Women)
An easy slip-on that instantly makes a simple outfit feel a little more polished without sacrificing comfort.
Frye Faith Mule
Boat shoes are having a moment again, but this pair feels timeless enough to wear long after the trend fades.
Sperry Slim Boat Shoe (Women)
They’re the perfect everyday sneaker when you want something classic with a little personality.
adidas Gender Inclusive Samba OG Sneaker
The suede gives this iconic sneaker a softer, more autumn-inspired feel that’s perfect for transitioning into cooler weather.
Nike Cortez Suede Sneaker
Some shoes never go out of style. These are the pair I’d reach for when I want to keep an outfit simple and effortless.
Converse Chuck Taylor® All Star® Low Top Sneaker ...
Every fall wardrobe deserves a great Chelsea boot, and these are the kind I’d wear for everything from errands to weekend trips.
Madewell The Benning Chelsea Boot
A timeless ankle boot that works with dresses, denim and trousers. The kind of purchase you’ll never regret.
Madewell The Darcy Ankle Boot
If I could splurge on one pair of boots, it would be these. They’re classic, beautifully made and exactly the kind of piece that only gets better with age.
Frye Campus Knee High Riding Boot
Bags
These are the styles I’d happily carry all fall, whether I’m running errands, heading to dinner or packing everything I need for a weekend away.
The brown colour makes this everyday staple feel especially elevated for fall. It’s the bag I’d grab for coffee runs, walks and weekends.
Everywhere Belt Bag
A timeless crossbody that proves classic pieces never go out of style. This is the kind of bag I’d love to own forever.
Louis Vuitton Trotteur Monogram Handbag
Perfect for dinners, weddings or any occasion that calls for something a little more polished without being over the top.
Loeffler Randall Delphine Leather Clutch
Simple, understated and endlessly versatile. This feels like the everyday shoulder bag I’d reach for without thinking twice.
Coach Brooklyn Shoulder Bag 39
If I had to choose one tote for fall, this would be it. The woven leather gives it just enough texture while still feeling timeless.
Madewell The Handwoven Leather Tote
Accessories
These are the accessories I’d wear on repeat because they add just enough character without ever overpowering an outfit.
A beautiful leather belt is one of those pieces that quietly pulls an outfit together. I’d wear this with everything from denim to dresses.
Madewell Lucie Belt
The easiest way to make an outfit feel casual, polished and effortlessly cool all at once.
'47 MLB Mini Logo Baseball Cap
A simple knit beanie that feels just as at home on a morning walk as it does on a weekend trip to the farmers’ market.
prAna Teenie Beanie
More than just a scarf, this is the layer I’d keep in my tote for chilly mornings, road trips and flights.
zestt organics The Dreamsoft Travel Scarf
A modern shape that instantly gives even the simplest outfit a little more personality.
I-SEA Geometric East West Rectangle Sunglasses
Classic aviators never really leave my wishlist. They’re timeless, flattering and work with absolutely everything.
AIRE Whirlpool Aviator Sunglasses
The everyday earrings I’d put on once and forget to take off because they go with everything.
Madewell Demi-Fine Huggie Hoop Earrings
A little more texture, a little more shine and still understated enough for everyday wear.
Madewell Hammered Puffy Small Huggie Hoop Earrings
When I want my jewelry to make a statement without feeling overly dressy, these are exactly what I’d reach for.
Madewell Hammered Sculptural Double-Hoop Earrings
A beautiful watch is one of those timeless accessories that never feels trendy. It’s the perfect finishing touch to an outfit.
BREDA Jane Revival Bracelet Watch