If I Were Starting My Winter Wardrobe From Scratch, I’d Buy These Pieces

After years of refining my wardrobe, I’ve found myself reaching for the same pieces again and again, and this year is no exception. These are the staples that make getting dressed feel effortless: beautifully cut skirts, perfectly broken-in denim, crisp shirts, and accessories that pull everything together without a second thought. Taken together, they almost form a capsule wardrobe: one that works just as well at home as it does packed neatly into a carry-on for a weekend away (for those of you who always ask!). What I love most is that nearly all of these pieces transcend seasons, and because I wear them so often, the cost per wear has quietly dwindled to pennies. They’re the kind of thoughtful, hardworking investments that simplify your closet and make every outfit feel like you.

A flattering sweater dress in a solid color is a piece you'll reach for all season. A wardrobe workhorse that looks put together and yet is as comfortable as pajamas. Three favorites: the speckled oatmeal merino midi I'm wearing above reminds me of The Row, my cream ribbed knit midi is so pretty with a statement belt (seen here) or necklace, and the tie waist on this brown wrap dress is incredibly flattering. All three work with tall suede boots or pumps all season long.
Leopard suede ballet flats are my secret for grounding any outfit, and they're incredibly comfortable.
Nothing peeks out of a sweater cuff better than my lab diamond tennis bracelet, a staple in my daily rotation. (I also own and love this.)
This blue cropped jacket made with Linton Tweed adds instant polish to everything from midi skirts to high-waisted jeans.
Best-selling and under $200, this olive corduroy mini dress goes with ballet flats, loafers, pumps, or tights and boots.
I have this dark denim midi skirt in three colors, and it's so pretty with tall boots and sweaters.
Light wash, non-stretch, and perfectly straight, these high-waisted jeans are my everyday pair with chunky sweaters and loafers. These relaxed jeans have a slightly lower rise and are so comfortable I can do long-haul flights in them.
A khaki cotton trench coat with a beautiful drape, perfect over cashmere sweaters now and sundresses in spring. The fabric is almost identical to the iconic Burberry gabardine, but much easier on the wallet! (I also own and love this one.)
Mother-of-pearl buttons and fine-gauge cotton-silk make this ribbed henley the perfect layer under a tweed jacket.
Wear this tiger's eye necklace long or doubled up for instant warmth on button-downs and sweaters.
If you love a tall pointed-toe suede boot, these stiletto boots are a splurge I wear constantly (the croc-embossed heel is such a chic detail), but I also got these dark brown suede boots, which are almost identical for a fraction of the price. Both look polished with midi dresses and jeans all winter.
Ok, this cable knit cashmere lounge set ($50 off with STACIE50) is the most flattering set I own, and I've worn it in a cabin in Maine and out to dinner in Manhattan. (And it's machine washable!)
Under $200, this bestselling cashmere slim turtleneck is an easy, warm layer on its own tucked into skirts or trousers, or layered under any blazer or coat. (You'll want one in every color!)
This slim-cut button-up shirt is a wardrobe MVP. The tulip-shaped hem means it stays tucked, and I love pairing it with jeans and a chunky necklace, or layered under a cashmere sweater or blazer. (I wear it so much I have two of the same white shirt.) This stand-collar shirt is another go-to, and the oversized fit is gorgeous with statement skirts or pants.
These high-waisted wide-leg jeans elongate your figure and are a nice, dressier version of your favorite wardrobe staple. (I like them best with these boots.)
These pumps are the most perfect heels ever created. So comfortable I have them in 6 colors.
I love a long-sleeved silk dress for winter dinner dates and occasions, and I'm obsessed with this blue paisley silk dress and this berry-hued paisley silk dress (20% off with StacieF20), both of which look great with knee-high boots now and heels when it warms up.
Classic menswear-inspired suede loafers look so polished with cropped jeans and a cozy sweater. (I have the iconic Gucci loafers, but they aren't as comfy or flattering!)
A checked blazer is the hardest-working third piece in a winter closet, and there's one for every budget. The blue and camel check on this cashmere-blend boyfriend jacket feels relaxed, while this double-breasted checked blazer is a splurge with exceptional Italian tailoring. This houndstooth blazer gives you the look for a fraction of the price. Throw any over a turtleneck and jeans.
Fair Isle always feels right in winter, and this Fair Isle turtleneck is my most-worn version of the style. Throw it on with a Barbour coat for dog walks, or with a camel wrap coat for a day running around town.
Rosewood cords are the PERFECT fit, with just enough stretch for busy weekdays and weekends.
I love a statement skirt that can be dressed up or down, and this tiered midi skirt works for the office with a blazer or on a date with a silk top.
Every closet needs a Barbour, and this navy waxed jacket only looks better with age. (I like to size up, and wear a US4/UK8.)
My most-worn brown suede booties have a low heel that makes them an everyday go-to with jeans or cords.
Contrast binding on the collar and patch pockets makes this Prince of Wales plaid coat so charming over jeans.
This chunky cocktail ring is a true splurge I wear almost daily, and it makes even a cozy sweater feel special.
The gold knot hardware on this saddle suede belt (20% off with StacieF20) dresses up denim and sweater dresses alike.
In winter, your coat is often your whole outfit, so be sure to have one fun style in your collection. This checked wool trench coat makes jeans and a sweater feel instantly polished, all winter long. Same goes for this, this or this!
A structured leather shoulder bag is the accessory that pulls every winter outfit together. I carry this acorn vacchetta saddle bag constantly (it ages to a beautiful patina and converts to a crossbody), and my horsebit bag adds instant equestrian polish to denim and knits. For under $500, this classic leather bag with three strap lengths is such a smart buy.
I'll argue a camel wrap coat is the most versatile piece of outerwear you can own. Throw it on over loungewear and clogs, or pair with a cocktail dress and heels. Mine is 5+ years old from Brooks Brothers (new season here), but Max Mara is the king of this category and has loads of beautiful options like this, or get the look for less with this.
Cozy and polished, this iconic cable knit cashmere sweater has a relaxed fit made for jeans and boots on weekends or throwing over your shoulders with a slip dress for a date. (I size up for the perfect fit.)
I collect cashmere-silk scarves, and they're such an elegant way to add warmth. My top two favorites right now include this burgundy floral version and this navy bandana print.
Everyday diamond studs like these go with absolutely everything, from lounge sets to holiday dinners. (I also have these and get them confused with my diamonds all the time!)