What to Wear on Winter Date

Winter is the best time to go on a date. The weather is cold and you can snuggle up with your date under a blanket, or even in a heated car! But what should you wear? Winter is the best time to go on dates. It’s cold, it’s dark, and you have to bundle up together! It’s a perfect storm of romance-inducing conditions. So what do you wear on a winter date? We’ve got you covered with some tips and tricks to keep you warm and looking hot in the winter months.

What to Wear on Winter Date

Winter is the best time of year to go on a date. It’s cold, it’s snowy, and you can bundle up in layers and snuggle together while you watch the snow fall outside. But if you’re like me, then you’re also busy and don’t have time to think about what to wear on your date—which is why we’re here today!

Let’s start with what not to wear: no jeans! Jeans are great for the summer because they’re casual and easy to move around in, but when it’s freezing out? They’re just going to make you feel even colder than you already are. Instead, try wearing leggings or stockings under your pants—they’ll keep your legs warm without being too thick or uncomfortable.

Next up: hats! Hats are an absolute must-have for winter dates because they keep your head warm without messing up your hair (and let’s be real, who wants their guy seeing their frizzy hair after they’ve been outside?). You should definitely invest in one before going out with him so that he doesn’t have any excuse not to kiss those rosy cheeks later on in the evening!

The winter months are upon us, and what better way to spend them than with your beau? If you’re looking for tips on how to look great on your date, this article is for you.

We’ve rounded up some of our favorite winter date outfit ideas that won’t leave you feeling cold or uncomfortable. From casual to dressy, we’ve got everything covered!

A cardigan and slip dress are a classic date-night combination. Just throw a coat over it and you’re ready for winter. A belted blazer dress can go from fall to winter with the simple addition of tights. Never underestimate the power of a cozy sweater, perfectly fitting jeans, and luxe-looking boots

Winter Date Outfit Ideas That Are Cute and Comfortable

Date night during the winter months can be a tricky event to navigate. Something you typically look forward to can become something you dread. Trying to put together an outfit that won’t leave you feeling cold or uncomfortable but still make you feel like the best version of yourself is a particularly difficult task. Throw a pandemic into the mix, and well, winter date nights really can’t be totally spontaneous. The little dress or pretty top you reach for during the warmer months just won’t cut it in the wind, rain, or snow. 

We’re here to help with a slew of outfit ideas that will turn winter date nights into the fun, romantic activities that they’re meant to be, even in cold weather. Just because it’s cold outside doesn’t mean you need to sacrifice your style or relationship building. From leather pants to sweaterdresses to belted trench coats, we’ve got your outfit covered to ensure you feel cute while remaining comfortable. Whether you’re dressing up to safely dine outside or stay in, below are 21 winter date-night outfits that you’ll actually want to wear. 

What to wear on a winter date

Leather pants always lend a cool vibe, and a fitted sweater balances out proportions. 

A knit set always looks elevated. 

This feminine sweater and skirt juxtaposed with edgy combat boots create a perfect balance. 

A furry coat feels especially fun when paired with patent-leather pants and boots. 

Cute winter date looks

A matching sweater and knit skirt are equal parts cozy and chic. 

What to wear on a winter date

It doesn’t get any cooler than a printed maxi dress and knee-high boots. 

Winter date outfit ideas

A belted coat is as timeless as it gets. Throw one on over an all-black outfit for instant polish.

What to wear on a winter date

A ribbed-knit dress with cutout detail is guaranteed to garner compliments. 

Winter date looks

A leather dress is cool on its own, and adding knee-high boots just doubles down on that fact. 

Cute winter date outfit ideas

A cutout sweater adds interest to any outfit. 

What to wear on a winter date

A cardigan and slip dress are a classic date-night combination. Just throw a coat over it and you’re ready for winter. 

Cute winter date outfit ideas

A belted blazer dress can go from fall to winter with the simple addition of tights.

Comfortable winter date outfits

Never underestimate the power of a cozy sweater, perfectly fitting jeans, and luxe-looking boots. 

Winter date outfits

Here’s proof you can never go wrong with a hint of sparkle and a red lip.

What to wear on a winter date

An open-back top is always a good idea for date night, and leather pants make it feel seasonal.

Winter date outfits

Throw your favorite slip dress over a long-sleeve top of similar color for a sophisticated, monochrome look.

Winter date outfits to try

A turtleneck-blazer combination is a classic, so pairing the pieces with leather pants and boots keeps the look feeling special. 

What to wear on a winter date

Although you may need to add a coat, the pairing of a sweater and leather skirt is one perfect outfit. 

Winter date outfits

Not only is a tailored suit classic, but it’s also ultra-comfortable. Just add heels to make it feel date night–ready.

Comfortable winter date outfit ideas

Make your leather shorts work for winter by layering them over sheer tights for a night out. 

What to Wear on Winter Hike

Winter hiking is a popular activity in the colder months, but it can be hard to know what to wear.

You want to make sure you’re prepared for your trip, without going overboard and weighing yourself down with too many layers.

We’ve compiled a list of some of our favorite winter hiking outfits, so you can enjoy time outside without freezing!

Hiking season doesn’t have to end with the arrival of winter. With the right clothing, you can enjoy your favorite day hiking trails all year round! In this post, we share the gear that helped us embrace winter and fall in love with cold-weather hiking.

Michael standing in the snow looking out at Crater Lake
There’s a Scandinavian expression that captures the essence of winter hiking: There’s no such thing as bad weather, only bad clothing.

For years, we felt we had to “get through” winter. It’s cold, dark, and miserable, so we would hunker down and wait for it to be over. Going for a short walk around the neighborhood, never mind going on an actual hike, was out of the question.

All that changed when we decided to invest in proper cold-weather hiking gear. It is no exaggeration to say having the right clothes reshaped our relationship with winter.

Now, with the right apparel, hiking in the winter has become its own unique outdoor experience we look forward to as much as summer hiking!

Half Dome covered in snow as seen over the Merced River in Yosemite Valley
Even in popular spots like Yosemite, winter hiking means fewer crowds! We saw very few people on this hike.
Pros of Winter Hiking:

No crowds
Stay engaged in an outdoor activity all year long
Experience your favorite trails from a different perspective
In this post, we’ll go over the basics of layering, tips to keep warm and dry, clear up a few misconceptions, and offer our recommendations for our favorite cold-weather hiking gear. Being a little cold is one thing. But being cold and wet can become very dangerous, very quickly. Water conducts heat away from the body 25x faster than air.1 That rate of cooling can rapidly become unsustainable and deplete your core temperature within minutes. So the name of the game is to stay dry!

The good news is there are only two ways to get wet: from the outside and from the inside.

The external factors are pretty obvious. Rain, melting snow, stepping through the ice, or a slushy puddle. Basically, anything around you that is wet, or can become wet, if exposed to the heat of your body (i.e. snow & ice). You want to select clothing that will keep that water moisture out.

The less obvious factor is getting wet from the inside. Physical exertion will cause you to sweat. You might have a perfectly waterproof shell on the outside, but if you’re overheating and sweating under your layers, you’re still getting wet. And once you stop moving, all that sweat will start cooling your core body temperature very quickly.

So the goal is to be comfortably warm but not so warm you sweat. Since hiking has variable levels of exertion (hiking uphill is more taxing than going downhill) you’ll need to be able to adjust your clothing accordingly. This brings us to our next point….

Layering For Cold Weather And Winter Hiking
This often misunderstood concept is the basis for how to dress for every winter outdoor activity.

You want to be able to adjust your layers to match your current level of exertion.

Start with a base layer, which traps a thin layer of heat against your body and wicks away any moisture if you do begin to sweat. Synthetics or Merino wool are ideal materials. Cotton needs to be avoided as it holds onto moisture.

Next is a mid-layer which provides the bulk of your insulation, trapping your body heat to keep you warm. Common mid-layers are down or synthetic puffy jackets. You can also break your mid-layer into two parts: a fleece and a light puffy jacket. This will give you more layers to progressively scale through as your body temperature changes throughout your hike.

Finally, you should have a waterproof and windproof external shell. This will keep external moisture out and block the wind—wind rapidly accelerates cooling the same way that water does (even more so if there is moisture present). If it’s a calm clear day, you might not need to wear it at all, but it’s always recommended to have it with you.

Megan stuffing a jacket into a hiking daypack
One commonly overlooked part of the layering system is having someplace convenient to put your layers when you don’t need them—which is why it’s so important to have a daypack with you.

If you don’t have anywhere to put your layers, you’ll be tempted to keep them on and just push through. (We have been guilty of this in the past!)

The moment you feel yourself getting a little too warm, you need to stop, open a zipper, push up your sleeves, or strip down a layer.

Conversely, the minute you start feeling a bit chilled, you should add a layer—it’s far easier to stay warm than it is to get warm.

This process should be easy, quick, and convenient. If you’re covering terrain with a lot of variation in elevation, you want to really make a habit of adjusting your layers frequently.

What To Wear For Hiking In Winter
Below we’ll cover—from head to your toes—all the winter hiking apparel you want to consider before heading out into the cold.

Starting At The Top
A good Merino wool or synthetic beanie is invaluable. We’re not sure exactly how much heat you lose through your head, but personally speaking, our feeling of warmth is directly correlated to wearing a cozy hat.

Black beanie product image
REI Co-Op Beanie

While beanies come in all shapes in sizes, I prefer those that contour closely to the shape of my head. I’m not really into the droopy top Smurf Hat look. This REI Co-Op Beanie is a perfect no-frills hat made from a blend of wool and synthetics.

This beanie is perfect for active winter hiking. It’s thin and lightweight, which means you won’t break into a sweat the moment you put it on. Merino wool fabric is moisture-wicking, breathable, and anti-odor. Plus it comes in really fun color blocking!

Neck Gaiter, Buff, or Scarf
A wool or synthetic gaiter is a great way to trap warmth from escaping up your collar. You can also pull it up over your mouth and nose to cut down on the wind. After 2020, I’m pretty sure we are all pretty familiar with these things. Oy vey!

Wool gaiter product image
Buff Lightweight Wool Gaiter

They make thicker ones for when it’s really cold out, but I prefer a lightweight Merino wool neck gaiter. Just enough to keep the heat in and cut the wind without overheating.

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Polarized Sunglasses
A bluebird day might be great for a winter hike, but bright white snow can quickly become blinding. Polarized sunglasses do a great job of cutting down the glare. If it’s particularly cold and windy, snug-fitting goggles might be good options instead.

Sunglasses product image
Sunski Treeline Sunglasses

We can’t say enough good things about Sunski sunglasses. Great products, a real deal lifetime warranty, and very reasonably priced. This model is called the Treeline and comes with polarized lenses and detachable side sun blinders to keep light from leaking in from the periphery.

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Balms, salves and sunscreen
The dry winter air can wreak havoc on your skin and as always, an ounce of prevention is worth a pound of the cure, so make sure to apply (and reapply) chapstick and lotion to exposed skin. Also, sunscreen! Sunlight reflecting off snow can burn your skin quicker than on a hot day on the beach. So stash these in your day pack and apply regularly!

Megan hiking on a snowy trail. She is wearing a wool baselayer top and winter hiking pants.
Winter Hiking Jackets, Shells, And Base Layers
Base Layer Top
A base layer top traps heat close to your body and wicks moisture away, but it should also be something that’s soft, cozy, and flexible. Merino wool or synthetic are ideal materials.

REI 185 Base layer top
REI 185 Merino Wool Base Layer Top

I personally like a midweight baselayer top like this 185 weight top from REI. The merino wool traps a lot of heat close to my body and wicks away any moisture that develops. These are super versatile long-sleeved shirts that are great for around the house or as a base layer on a hike.

This quarter-zip from Smartwool gives you the ability to open it up a little to regulate your body temperature. Basically, it can go from being as open as a polo shirt to as snug as a turtle neck just by adjusting the zipper.

Choose a sports bra that contains zero cotton. Everyone has different needs out of a sports bra and should choose accordingly. I personally like the Patagonia Barely Sports Bra.

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Megan walking on a snowy trail with Wizard Island in the background
Insulating Mid-layer
Your mid-layer is where the bulk of your insulation will come from. The most common forms of insulation are down and synthetic (usually PrimaLoft). They both have their pros and cons, but it basically boils down to: Down weighs less but will stop insulating if wet, synthetics weigh more but will (kinda) continue insulating if it gets wet. Again, ideally speaking, this layer should never get wet.

Better Sweater Quarter Zip Better Sweater Quarter Zip product image
Patagonia Better Sweater

This quarter-zip pullover sweater is our lightest and most casual mid-layer for winter hiking. We use this a lot of around-town hikes on milder days. On its own, it is great for temperatures in the 40’s F, and when paired with a vest (below) and it can be good down to the low 30’s.

A sweater & vest combination is a great flexible option for a winter hiking mid-layer. A puffy vest ensures that you’ll be able to keep your core warm, and the sweater gives a little something for your arms. This setup offers a little more flexibility while reducing the overall bulk of your outfit.

Patagonia’s Nano Puff Jacket is a great mid-layer option that features synthetic PrimaLoft insulation. I like that it’s not as puffy as a down jacket, so it fits better under other layers and packs away easily when I’m not wearing it.

As far as down jackets are concerned, the REI Co-op 650 is an incredible value. It’s filled with 650 RDS-certified down so it’s warm and insulating, but it comes with a lower price tag than many other down jackets on the market.

This is another one of our go-to puffy jackets. 800-Fill traceable down, recycled ripstop polyester, and comfortable elastic cuffs. But my favorite feature is the interior pocket that doubles as a zippered stuff sack. This makes it super easy to put into a day pack.

Are you cold all the time during the winter? Then the Magma 850 down hoodie is the jacket for you! With 850 fill power goose down, it’s the warmest jacket on this list. It features water-resistant down, abrasion-resistant Pertex ripstop nylon, ergonomic shoulder seams for carrying a pack, and zip pockets positioned to be compatible with a backpack’s hip belt. Best of all, it compresses down and can be packed inside its own pocket!

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Outer Layer Shell Jacket
A weatherproof shell is designed to keep all external moisture (and wind) out. Look for synthetic materials with a waterproof membrane, stretch fabric, zipper vents, adjustable hoods. Your shell also needs to be large enough to go over your mid-layer, so you might want to consider sizing up.

Blue rain jacket product image
REI Co-op Rainier Rain Jacket

Waterproof, windproof, and breathable, the REI Co-Op Rainer Jacket is technically a rain jacket but it’s designed to repel any type of precipitation. Pit zips allow you to vent out excess heat, the 3-way stretch fabric offers excellent flexibility, and a 3-point adjustable hood keeps your beanie dry.

When it comes to rain jackets, there is always a delicate balance between waterproof and breathable. But if you ever find yourself caught in the freezing rain, you’re going to want a jacket that is actually waterproof. And the Patagonia Torrentshell is actually waterproof. It also features storm flaps, a 2-way adjustable hood, and pit zips.

Gloves / Mittens
There is a big divide between glove people and mitten people, but we think the best solution is a hybrid approach: glove liners + mitten shell. A thin glove liner is great for maximum dexterity when you come to a stop. But when you’re hiking and don’t need your hands, mitten shells offer water and wind protection.

These Polartec fleece gloves are fairly warm and aren’t bulky, so you retain a fair amount of dexterity when wearing them. They are touchscreen compatible and made from sustainable bluesign-approved materials.

These gloves are perfect if you want something more substantial than a liner but not as bulky as a pair of mittens. Designed with touch-screen compatibility, you’ll have no trouble using your phone to navigate or take a quick picture out on the trail.

These are waterproof and windproof outer shells for your gloves. You may not need them, but if the weather turns, you’ll be thankful you have them.

This is a great pack for winter hiking. The large top-loading zippered pouch makes it really easy to stuff layers into, while the top and bottom compressions straps allow you to cinch it down into a compact unit. We also love all the ergonomic features like adjustable shoulder and hip straps.

The more layers you bring with you, the larger your day pack needs to be. This 40-liter pack by REI is a great option for colder winter hikes. It has plenty of room for extra layers, food, water (and even some of your hiking partner’s stuff!) It features one large interior compartment, an adjustable hip belt, hiking pole straps, and a waterproof rain shell.

Insulated Water bottle
Even though you shouldn’t be sweating, winter air can be very dry and you’ll lose a lot of moisture through your breath. So you will want to bring water with you to stay hydrated.

We like to fill insulated water bottles with lukewarm water, which is perfect when it’s really cold outside. As a special treat, we also like to bring along an insulated bottle of coffee, hot chocolate, or tea.

Blue water bottle product image
Hydro Flask Insulated Water Bottle

We have a variety of Hydro Flask insulated bottles that are perfect for winter hiking. Water, coffee, tea, hot chocolate. So long as it’s not frozen, we’re into it!

Hydro Flask Food Jar

Hydro Flask also makes a wide-mouthed insulated food jar. This can be great for soups & stews, chili mac, or any other warm meal you want to enjoy on the trail.

Winter Hiking Pants And Baselayers
Base Layer Pants
Depending on the temperature, you may want some base layer bottoms. Most are designed to be worn without underwear. This is good because most underwear is cotton-based, which you don’t want to be wearing.

Smartwool baselayer legging product image

These are my new favorite base layer, which I wear throughout winter even when I’m not hiking. Just like my Smartwool top, these bottoms are super comfy while providing a thin layer of warmth close to my legs. On a really cold day, wearing a bottom base layer really takes the edge off.

This is a more affordable synthetic version of a bottom base layer from REI. Same concept, different fabric.

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Mid-Layer Bottoms
While mid-layer bottoms are technically a thing, it’s more common for downhill skiers and snowboarders. There are options out there if you are interested, but our legs never get that cold and we think it’s far too cumbersome for hiking in.

If it’s really cold out, we’ll wear our ski pants with wool base layer bottoms. And if it’s really really cold out, we’ll stay home and play checkers.

A woman hiking in snow
Winter Hiking Pants
A good pair of winter hiking pants should be, at a minimum, water and wind-resistant. Pants with a DWR (durable water repellent) coating on the fabric means that water will bead off, though in a downpour waterproof pants would be a safer choice–or pack a pair of rain pants to put over your hiking pants if you encounter rain.

Women’s winter hiking pants product image
REI Activator Soft Shell Pants

I wanted a pair of winter hiking pants that would be water and wind-resistant, have a bit of stretch, be roomy enough to wear base layers under, and cost under $100. These REI Activator Pants checked all those boxes (and offer 50 UPF protection).

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Sahara lined pants product image
REI Sahara Lined Pants

For hikes that will be really cold–or if I don’t want to have to wear a base layer under my pants, these fleece-lined pants are perfect. They have a DWR fabric to repel water, have a slight stretch, and are SO toasty.

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Mens winter hiking pants product image
prAna Stretch Zion

I hiked the JMT in a pair of prAna pants and I still think they’re fantastic. The fabric in these Stretch Zion pants is incredible. Water-repellent, 4-way stretch, UPF 50+, and abrasion-resistant – all while feeling incredibly soft against the skin. The pants are also loaded with a lot of subtle technical features but still look sharp enough to wear around town. They come in an expanded range of sizes, too. Awesome pants, really recommend them.

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Grey winter hiking pants
Kuhl Silencr

These are my first pair of Kuhl pants and I’ve been really happy with them so far. The ripstop soft-shell Reflex fabric is really durable yet flexible and has a water repellent (DWR) finish to fend off light snow/rain. The ergonomic construction and stretch fabric allow for a great range of motion. They are fast becoming my go-to winter pants.

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PS: I was initially concerned about all these pants because of the snap button waist. (A feature on all Kuhl pants.) I didn’t want something flimsy that would pop open every time I bent over. But thankfully the snap is really heavy-duty, with a lot of positive resistance when closed. It hasn’t accidentally opened on me once.

Megan walking with trail crampons attached to a pair of winter hiking boots.
Using Hillsound trail crampons provides extra traction on snowy trails.
Winter Hiking Boots And Footwear
Wool Socks
Resist the urge to wear super thick hiking socks! Those might be fine around the house, but putting thick socks into already snug-fitting boots is a recipe for loss of circulation. Your feet will stay warmer if there’s a little bit of space in your boots. You may want to pack an extra pair of socks to switch into if your first pair gets wet.

Darn Tough socks product image
Darn Tough Socks

These are our standard year-round go-to socks with an incredible lifetime warranty program.

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Toe warmers
If your feet are chronically cold while hiking 1.) consider sizing up your boots—this will allow you to wear thicker socks while maintaining good circulation. 2.) consider using toe warmers.

Ignik Toe Warmers
Ignik Toe Warmers

These single-use toe warmers come in a flat pad that fits under the ball of your foot. They take about 5 minutes to activate then remain warm for upwards of 6-8 hours.

Shoe Gaiters
If you’re going to be trekking through deep snow or powder, it’s worth considering a pair of shoe gaiters to keep snow out of your boots. For winter hiking, you are looking for something waterproof and potentially insulated (unlike lightweight hiking/trail running gaiters).

Shoe gaiters product image
Outdoor Research Gaiters

These gaiters are available in high or low, depending on the snow depth you’re likely to encounter. However, if you’re wearing water-resistant pants, then the main goal is to keep snow out of your boots. So our thought would be to go with a lower-cut gaiter.

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Waterproof Boots
If your hike will take you through any amount of snow, it’s essential to have waterproof boots. Snow might not seem wet, but before long the heat from your feet will melt it. So it’s essential to have some type of waterproof system.

Oboz Bridger Insulated Boot
Oboz Bridger Insulated Waterproof Boots

A good pair of winter boots can make cold-weather hikes feel like a walk in the park! These insulated, waterproof hiking boots by Oboz have been a crowd favorite for years. While we don’t personally own these boots (yet!), our friends do, and they’ve nothing but great things to say about them!

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Merrell Thermo Chill Mid Waterproof Boot
Merrell Thermo Chill Mid Waterproof Boots

A waterproof membrane, low-volume insulation, deep rubber tread–these are great all-around winter boots.

Pro Tip: If you don’t want to spring for a pair of winter boots, you can Scotchgard your summer hiking shoes the night before your hike to keep moisture out. It’s not as fool-proof as actually buying waterproof boots, but it will work!

Microspikes or crampons
Slipping on a patch of ice is one of the fastest ways to turn a pleasant winter hike into a trip to the emergency room. You might think your boots have good treads, but once you’ve worn microspikes you’ll have a whole new appreciation for good traction. In slippery, icy conditions they are absolute game-changers. Unwalkable sections of the trail suddenly become a stroll in the park.

Hillsound Crampons

These are the crampons we own and are a solid choice for hiking on packed snow or ice. We keep them in our car and throw them in our packs on all our hikes during the winter and never regret having them with us.

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Microspikes product image
Kahtoola Microspikes

We haven’t used these personally, but these microspikes are another choice that is popular with PCT thru-hikers for the snowy Sierra sections.

Snow Shoes
If you live in an area where there is a lot of deep snow cover during the winter, snowshoes might be the only reasonable way to “hike.”

Choosing a pair of snowshoes is worthy of its own separate guide, but there are lots of options to choose from if you’re looking to get started.

MSR Evo Snowshoes

MSR’s EVO snowshoes are a crowd favorite and are consistently one of REI’s top-selling snowshoes year after year. They are compatible with shoe sizes as small as 6 women’s (4.5 men’s) and as large as 15 men’s. If you’re interested in learning more about snowshoeing, REI has a great Snowshoeing 101 guide you should check out.

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