Three Ways to Transition Your Wardrobe to Winter

Pack away some stuff, refresh others, and bring the cold-weather favorites out of hibernation.

No matter what Fitzgerald says, life doesn't have to start all over again when it gets crisp in the fall. Sure, you’re no longer wearing some of your summer staples now that bourbon and bonfires have replaced beers on the beach. That’s obvious. But thanks to the money-saving and stylish practice of layering, transitioning between seasons doesn’t have to be a total closet overhaul.

To avoid ditching your current wardrobe entirely to stock up for winter, follow this guide for which summer items to retire, which items can transition to your winter wardrobe and which essential cold weather items you need for a good wardrobe refresh.

To Retire

These are the items you want to stash away until next summer.


This should be obvious but in case it’s not: shorts season is over. Yes, even on those last few unseasonably warm days of the fall. But looking ahead to your winter wardrobe is a great time to take stock of your summer items and decide whether you’ll want them around next season. If your favorite pair suffered some irreparable barbeque stains this summer, now’s the time to ditch them.

Low-Slung Loafers

Colder temps come with raking leaves, hot toddies, and one other important thing: socks. Bare ankle season has officially passed. Especially as the threat of snow and sleet starts to get more menacing, a solid pair of shoes that won’t fall victim to puddles of slush is a must. That means it's time to pull out your higher-cut boots to keep your feet warm and well-protected once the rain and snow sets in, and on a dry day, you can keep your same lower-cut kicks current with a quality pair of socks.

Linen Anything

Even when you're piling on layers, linen doesn’t do well in the colder months. On one hand, it’s impractical. Linen is an incredibly light fabric (which is the entire reason it’s such a sold staple for your summer closet), but it’s also extremely prone to wrinkling. In other words, it won’t hold up well when bunched under a heavyweight knit cardigan or layered under a quilted vest. Secondly, unlike other more versatile cotton pieces that blend well in both summer and winter wardrobes, linen has a distinctly summer feel. Once fall hits, it’s just out of place.

To Reboot

These are your go-to transition pieces.


Consider the humble tee the Swiss army knife of your closet: you’ll never regret having one on. And obviously, your favorite summer tees transition just fine into fall and winter when layered appropriately. To keep them looking current (and to keep you from freezing) in the colder months, layer your t-shirts under items with a little more weight to them: heavy knits, extra-sturdy flannels, raglan crew necks, denim jackets – you get the idea.

Light Jackets

Speaking of jackets, your light and medium weight layers can also be year-round closet staples. But rather than tossing your waxed cotton coat over your t-shirt on a rainy day at the beach, you’ll be slipping it on over your sweater as extra wind protection. The same rule also applies particularly well to denim jackets. Black versions and darker washes are best for fall, but even if your current jacket is a summery light wash, it can still work – just layer it over a sweater or under an overcoat on especially cold days.

Jeans and Chinos

Jeans and chinos will always be season agnostic. To make your year-round staples especially current in the colder months, it’s all about the color palate. Onboard yourself to the world of seasonal transitions with foolproof dark wash denim. Like with denim jackets, lighter washes can still hold up through the leaves falling – you just have to switch up how you style them. Instead of a pair of canvas sneakers, look for a sturdier desert boot or suede Chelsea boot to pair them with.

For chinos, color is everything. Leave the bolder salmons and Kelly greens on the golf course for the season and keep your khakis, olives, and blues – or anything else neutral. Add a cap and a pair of boots and you're good to go.

To Refresh

These are the items worth a winter wardrobe investment (or reinvestment) this season.


With the exception of a couple of chilly nights on the beach, you haven’t thought about your sweaters in months. Dust off (read: dry clean) last year’s cable-knit crew necks and re-introduce yourself to sweater weather. To give your sweater collection a seasonal update, consider investing in either a color-blocked crewneck or shawl cardigan with a heavy knit for this winter.


Ah, the winter boot. Always worth the investment. Not only does your go-to pair have to keep your feet warm and dry, but they should also, you know, look good. As such, you’ll want to look for a pair that does double duty. If you’re a shoe fanatic and planning on buying a boot for every occasion, consider a pair of suede Chelsea boots in a rich cognac – they're boldly stylish, but not overly trendy. And while luxe, suede isn’t exactly practical in snow, so if you’re more of a one-size-fits-all-footwear-occasions guy, you can’t go wrong with a sturdy pair of Red Wings. Casual, respectable, and strong enough to stand up to Jack Frost.


Sturdy flannel is pretty much the number one winter wardrobe staple. And while plaid is all well and good, you subtler, more monochromatic options are out there, too. To keep the fit from wandering too far into your dad’s L.L. Bean territory, make sure the cut is slim and the sleeves hit the right point on your wrists. If it doesn't pass the test, head to the tailor – a good flannel shirt has enough seasonal staple status that it’s worth the trip.

Do all that, and you'll be ready to brave the cold winds like they're nothing. As for the stuff you won't need until next spring, stash it in that big suitcase that’s collecting dust under your bed or check your local thrift store for a vintage trunk that can do double duty as storage and grown-up apartment décor.

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