A Fashion Editor’s 14 Best Winter Clothes Deals

Whether you’re looking to revamp your entire winter wardrobe or update some beloved (and belabored) cold-weather staples, the beginning of fall is actually the best time to get started. I should know: I’m a fashion editor with almost 20 years of experience obsessing over all things style. That’s why I’m already filling my online shopping carts with cozy sweaters and coats while keeping an eye on emerging winter trends and versatile basics that can be easily packed for upcoming travel. 

To help get you started, I’ve included my winter clothes shopping list, along with some styling ideas, packing tips, and where I intend to wear some of these steals, which are up to 60 percent off at Amazon. Throughout my years of shopping just about every type of sale, I’ve developed an overarching strategy to make the most of my time without overspending. It’s simple, it’s obvious, and it works: Make a list. Before diving into this list, I encourage you to weed through your closet (now’s a great time to start a donation pile) and reflect on the past few times you’ve gotten dressed for work, a dinner party, a date, or whatever. Take stock of what you found yourself wishing you had in your closet — and what’s ready to be retired. 

Next, review your forthcoming slate of engagements. Do you have a destination wedding on the docket? A festive New Year’s beach trip in the works? A day with family that requires matching pajamas? Just write it all down. Then (and only then!), list the types of pieces that will accommodate both of these needs. Ta-da! You have your sale shopping list.

Dokotoo Cropped Trench Jacket

There comes a time in every fashion lover’s life when, on the road, you wish you’d packed the dang jacket. Am I right?! After too many times finding myself without a lightweight option, I’ve now made it my personal mission to always — always — bring along a trench coat, no matter the event or destination. Lately, I’ve been charmed by cropped versions that are not only ideal for a travel day but can be layered over a variety of outfits, making them a carry-on packing list must-have.

Levi’s 94 Baggy Jeans

Relaxed denim is a traveler’s cold-weather wardrobe’s best friend. To update a classic silhouette, consider a dyed pair in one of the most popular — and enduring — colors: dark green. This shade should be a mainstay in every fashion lover’s rotation. It’s subtly sophisticated, while the shape of the pants keeps things casual, ideal for a weekend road trip. An admitted book nerd, this fall, I’m driving to Oxford, Miss. to tour William Faulkner’s stomping grounds and take in the local scene. I’ll be donning these pants with a vintage Fair Isle sweater, a trench coat (never leave without one!), and comfortable, but cute, walking sneakers.

Free People Women’s Easy Street Tunic Sweater

If you’re anything like me, you’re always cold. Case in point: temperatures are still in the 80-degree range as I’m writing this(shout out to fall in the South!), and legitimately shivering. So, when I go to the airport, I make sure I’m armed with packable layers that can be easily tossed on without elbowing the person in the seat next to me. As a former overpacker, I’ve found that simple sweaters like this on-sale one from Free People can address freezing mid-air just as well as a highly air-conditioned museum.

Automet 2-piece Sweatsuit 

I have a confession to make: I’m a reformed athleisure critic. Here’s what happened. Early one morning during a girls’ trip, I found myself showered, but reluctant to commit to the outfit for the day. Badly in need of coffee, I donned a sweatsuit, much like this, tossed on a dramatic coat, and strolled to a nearby café. To a fervent always-on dresser, it felt scandalous. Why hadn’t I done this before?! Gone were the grumbling mornings spent itching in the clothes I would wear for the next 12 hours. I was forever changed. Now I’m convinced that, suitcase space permitting, one should always have cozy attire on hand for those in-between moments.

Puma Palermo Leather Sneakers

No one has time to be uncomfortable — especially when you’re traveling. These low-profile sneakers work on so many levels that they’ve achieved must-have status. I’ll definitely be popping on a pair when I’m headed to Austin for a wedding this fall. Not only are they ideal for a simple travel day outfit but they’re perfect for poking around all the vintage stores the town has to offer.

Karl Lagerfeld Paris Wool Coat

Flannery O’Connor once wrote that “a good man is hard to find.” I guess she never tried to buy a budget-friendly designer coat. Because, wow. Sale events like October Prime Day are the optimal occasion to pick up investment pieces, especially ones that you can wear throughout the years. Winter coats can, sometimes, seem a little drab, which is why invigorated pieces, like this knee-length wrap coat that features understated hardware along the lapels, feel fresh without being so trendy it’s bound to collect dust in your closet after a season.

Merokeety Half-zip Sweater

I’m a big fan of juxtaposing cozy staples with refined separates, especially for work trips. I love to pair a half-zip sweater with a leather-looking pencil skirt and sneakers. Throw on your favorite, classic white T-shirt underneath so you can wrap this around your shoulders if the conference room starts to get stuffy.

Nova Active Workout Set 

Yes, I am one of those annoying people who exercise on vacation. An avid runner, I love getting familiar with my surroundings on foot. But even if you can’t fathom squeezing in a sweat sesh not at the hotel spa, a matching set like this is ideal for brunch after one of those nights. For $22, this Nova Active set delivers a supportive, high-waisted pair of workout leggings and a matching sports bra (or workout top depending on your style).

Venecore Suede Clogs

After a night spent in high heels, having a cozy pair of clogs on hand, err…foot, will make all the difference the next day. But these aren’t just the light at the end of a stiletto tunnel. I love to wear slip-ons with warm socks for longer flights when I want to snooze. But to vamp these up for daytime, slip on your favorite wide-leg jeans, patterned socks, cable sweater, and you guessed it, trench coat, for a day perusing local bookstores.

Lillusory Cardigan

Chances are, it’s time to switch up your office sweater. You know what I’m talking about: the bedraggled knitwear that’s screaming for the dry cleaners from the back of your chair. I, for one, am more than guilty of relying on the same sweater for way too long. While chocolate brown is the color of the season, it never really goes out of style, making this cardigan a top contender for your office sweater update.

Zeagoo Satin Slip Skirt

The answer to every overpacker’s wishes, slip skirts work for a range of occasions without taking up too much suitcase real estate. These lend themselves to so many types of occasions and needs, from a casual rehearsal dinner and a night at the ballet to spur-of-the-moment drinks at the hotel bar. Regardless of where you’re headed, I find these look especially elevated when worn with a monochromatic top. 

Durango Harness Boots

A graduation from last season’s Western trend, harness boots are this year’s nostalgic footwear of choice. Sales are optimal for picking up trend-forward items, especially if you’re unable or uninterested in shelling out a chunk of change for pieces that’ll probably have a short shelf life. That said, I can’t wait to wear a pair of these with the above slip skirt and a slouchy sweater of the same color.

Badgely Mischka Leather Weekender Bag

The holidays call for plenty of long weekends and road trips to visit loved ones. A good quality leather weekender bag is the answer when you want to travel light without shouldering a mix of random tote bags. I like to keep a stash of essentials like toiletries, pajamas, and outfit basics in a weekender to take the fuss out of last-minute packing. This Badgley Mischka tote is a stunning choice, and it’s a sell-out risk. Don’t worry, I found another one that’s also heavily discounted, plus a spare lookalike version in case it meets the same fate.

Asics Gel-Kayano 30 Running Shoes

Look, I get it. Not everyone likes to run. We’ve covered that earlier. But on the off chance you feel like you might be bitten by the run bug (or you have a walking-heavy itinerary ahead of you), a supportive option, like these by Asics, is sure to keep you enjoying the scenery without blisters. I find a pair with black uppers to be a closet staple, too, as they look just as seamless with leggings as they do with a pair of jean shorts. You decide where you want to take them.