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Stay Toasty With These Winter Outfit Accessories

Scarves, socks, boots and other must-haves to meet cold weather head-on


a collage with various winter accessories in colorful circles
(From left) Stay cozy and look chic in these must-have winter accessories, including: FLX Women’s Quilted Flap Crossbody Bag in Black; Banana Republic Factory Women Faux Fur Scarf in Vino Rosso; Old Navy Women’s Rib-Knit Balaclava in Heather Gray; J.Crew Women’s Cashmere Blend Trouser Socks in Radiant Ruby; Clarks Women’s Cloudsteppers Breeze Faux Fur Slip-On Ankle Boots in Dark Tan Textile; and Isotoner Women’s SmartDRI Lined Stretch Fleece Gloves With Overlap Wrist in Leo.
AARP (Getty Images; Banana Republic Factory; Kohl’s, 3; J. Crew; Old Navy)

“Hat hair drives me crazy — it’s why I never wear one!”

“I can’t wear gloves and find my lip balm in my bag.”

“Aren’t there weatherproof boots that look stylish indoors?”

“I watched two scarf-wrapping videos on YouTube and gave up!”

Anyone who lives in a climate that does its own version of winter knows that having a hat, scarf, gloves and boots with grippy soles is a good idea. If that’s you, I bet you have all the above just waiting to tackle the incoming cold, rain, snow and icy walks. I also bet you have plenty of complaints about them. How do I know? I’m a fashion editor with a side gig as a personal shopper for women over 50 who bundle up while saying “I can’t wait for spring.” Time for an update. Here are six style solutions to make your winter woes disappear.

If you want: 

a collage with three different styles of hair friendly winter hats
(From left) Gap Women CashSoft Drawcord Hood in Black; Old Navy Women’s Rib-Knit Balaclava in Heather Gray; Heat Holders Women’s Alta Headband in Beige.
AARP (Gap, Old Navy, Macy’s)

1. A hair-friendly “hat.”

Swap your beanie for a knit balaclava or a sweatery hairband. They’re this year’s most fashionable trend and protect your vulnerable ears (which lack protective fat) from the cold and wind. The best part is their superpowers: both prevent flattening for those with bangs, thin hair or curly hair; ensure blowouts don’t deflate and dry out; and keep dry, damaged hair from turning frizzy and staticky.

How? Unlike beanies, balaclavas (also known as hoods), like the Old Navy Women’s Rib-Knit Balaclava in Blackjack, Heather Gray or Howlite ($17, oldnavy.gap.com), and the Gap Women CashSoft Drawcord Hood in Terra Brown, Kola Nut Brown, Black or Modern Red ($45, gap.com), are non-compressive and skim gently over your hair. Most feature a drawstring to adjust the closure around the face. They protect not only your ears and hair but also your neck — front and back — making a scarf unnecessary.

Wide, stretchy knit hairbands, like the Loft Brushed Knit Headband in Roasted Walnut or Cinder Gray Heather ($26, loft.com) and Heat Holders Women’s Alta Headband in Beige or Cloud Gray ($14, macys.com), leave the crown of your head free — a perfect solution for women who want ear coverage but think earmuffs look juvenile and say hats trigger headaches.

Both balaclavas and headbands stow easily in coat pockets or bags and come in a range of colors. For a polished effect, choose a shade that works with your coats and jackets or matches your boots and bag. And for a cheery approach to the season, or for anyone who prefers a pop of color, a goes-with-everything red never fails.

a collage with four different styles of neck warmers
(From left) Kookaburra by Ugg Women’s Koolafluff Pull Thru Scarf in Chestnut; Universal Thread Cozy Alpine Oversized Cable Triangle Scarf in Cream; Banana Republic Factory Women Faux Fur Scarf in Vino Rosso; L.L.Bean Women’s Wicked Plush Pull-Through Scarf in Midnight Black.
AARP (Kohl’s, Target, Banana Republic Factory, L.L. Bean)

2. A neck warmer and neckline filler.

Tired of trying to wrap, drape and tie a long scarf like a pro? Do you think prewrapped “infinity” scarves never sit quite right? Don’t say, “I give up! I’m wearing a turtleneck till April.”  Two new alternatives — knit kerchiefs and pull-through scarves — offer better neck coverage and fuss-free ease, along with a style refresh for all your coats and jackets.

Generously-sized, three-corner flat knit scarves, like the Universal Thread Cozy Alpine Oversized Cable Triangle Scarf in Red, Cream or Navy Blue (80-by-38 inches, $25, target.com), Echo Oversize Triangle Wrap in Camel or Black ($74, nordstrom.com) and the Madewell Women Knit Bandana in Crimson, Hthr Pecan, Midnight Navy or Pebble Gray (42.5-by-17.5 inches, $68, madewell.com) work the same way. All you need to do is tie two corners at the nape (as you would a bandana or lobster bib) and tuck the rest in. This fills the gap between neck and coat without extra bulk, and you can adjust any extra fabric by letting it softly drape like a cowl. And here’s a bonus benefit: Kerchiefs multitask as hats when tied beneath the chin, Audrey Hepburn- and Jackie O-style.

Predesigned “pull-through” scarves in fleece or faux fur, like the L.L.Bean Women’s Wicked Plush Pull-Through Scarf in Midnight Black ($33, llbean.com); the Banana Republic Factory Women Faux Fur Scarf in Black or Vino Rosso ($35, bananarepublicfactory.gapfactory.com); and Kookaburra by Ugg Women’s Koolafluff Pull Thru Scarf in Black or Brown ($38, kohls.com) sit higher on the neck for extra warmth and add a glam touch to plain puffers, tailored topcoats and barn jackets alike. No wrapping skills necessary!

a collage with four different styles of womens gloves and mittens
(From left) Isotoner Women’s SmartDRI Lined Stretch Fleece Gloves with Overlap Wrist in Leo; Lands’ End Women’s EZ Touch Screen Cashmere Lined Leather Gloves in Dark Walnut Brown; Echo Zip-Top Mittens With Faux Fur Lining in Forest Green; TrailHeads Women’s Running Gloves/ Convertible Mittens.
AARP (Kohl’s, Lands’ End, Bloomingdale’s, Target)

3. Phone-compatible gloves and mittens.

Funny how some trends become essential in the blink of an eye, like gloves that sync with our cellphone-at-all-times lifestyle. But not all touchscreen gloves are worth it. They need to be supple enough for dexterity when answering calls and texting or just scrounging in your bag for your car keys, but thick enough to keep your fingers toasty.

While once limited to a pretty unappealing bunch of gloves in black, new styles include touch-screen-enabled knits such as the Wild Fable Essential Glove in Brown, Navy Blue, Cream and Heather Gray ($6, target.com); sophisticated leathers, like Lands’ End Women’s EZ Touch Screen Cashmere Lined Leather Gloves in Dark Walnut Brown and Olive Drab ($90, landsend.com); and stylish leopard or bright red styles, like Isotoner Women’s SmartDRI Lined Stretch Fleece Gloves With Overlap Wrist in Leo or Red ($27, kohls.com).

Some women over 50 still love mittens, which can be warmer than gloves thanks to the shared finger space. The best choices for everyday use are flip-top styles that expose the fingers. They range from sporty styles, like TrailHeads Women’s Running Gloves/Convertible Mittens in Black/Reflective ($38, target.com), with a flip mitten top and touch-screen gloves beneath; to elegant embellished looks, like the French Knot Tilly Hand-Knit Convertible Mitten in Black ($82, nordstrom.com); and luxurious designs like the zipper-top Echo Zip-Top Mitten With Faux Fur Lining in Cinnamon Bark, Forest Green or Black ($104, bloomingdales.com). A reminder: When you’re outdoors in winter, your body prioritizes the circulation situation by sending blood to the heart, not your fingers! Gloves or mittens are not optional.

a collage with three different styles of womens winter boots
(From left) Toms Women’s Bennet Chelsea Boots in Dark Brown; L.L.Bean Women’s Rugged Winter Wellie Boots, Waterproof, in Burgundy Brown; Clarks Women’s Cloudsteppers Breeze Faux Fur Slip-On Ankle Boots in Dark Gray Textile.
AARP (Bloomingdale’s, L.L. Bean, Kohl’s)

4. Weatherproof fashion boots.

Take a look in your closet. You probably have a pair of cozy shearling slip-ons, waterproof rain boots and bulky snow boots. All practical choices that pair with leggings. So what’s missing? Short, stylish, insulated boots that are traction-secure but pair with real clothes to make changing into “indoor” shoes unnecessary.

Waterproof “shorties” are just tall enough to bridge the gap and slip easily under straight and boot-cut jeans and flared or wide pants. Unless you’re shoveling snow, styles like Skechers Women’s Hands Free Slip-Ins Relaxed Fit Easy Going Cozy Weather 2 Waterproof Booties in Taupe or Black ($90, dsw.com) with a knit cuff; Sorrel Women’s Kinetic Impact Puffy Zip Waterproof Boot in Black/Black ($160, zappos.com), a fleece-lined, sneaker-like style; and L.L.Bean Women’s Rugged Winter Wellie Boots, Waterproof in Classic Black, Burgundy Brown or Carbon Navy ($120, llbean.com), fleece-lined and slightly taller — like ankle boots that grew a turtleneck —  handle slushy parking lots, icy sidewalks and puddles efficiently.

If extreme snow and rain are not your concern but warmth and extra traction are, choose a water-resistant style, like Clarks Women’s Cloudsteppers Breeze Faux Fur Slip-On Ankle Boots in Dark Olive Textile, Merlot Textile, Dark Tan Textile, Dark Gray Textile  ($80, kohls.com) or Toms Women’s Bennet Chelsea Boots in Black or Dark Brown ($160, bloomingdales.com), both with a faux fur lining. All look as stylish as non-weatherproof versions and can handle a base layer of socks without feeling crammed at the toes.

So what’s the difference between water-resistant and waterproof? Waterproof boots are tougher, completely sealed and impenetrable, even in heavy snow or a downpour. Water-resistant means your boots can handle a drizzle or light flurries, but prolonged exposure to snow and stormy weather will eventually lead to wet boots and wet feet. Know which ones you need.

a collage with winter socks and leggings for women
(From left) Lane Bryant Fleece Lined Leggings in Black; Gap Women’s CashSoft Cable-Knit Knee-High Socks in Modern Red; Gold Toe Women’s 6-Pack Ribbed Crew Socks.
AARP (Lane Bryant, Gap, Kohl’s)

5. Snuggly tights and socks.

Funny thing, but hosiery gets no thought until your toes feel like icicles and drafts are wafting up your midi dresses. Buying seasonally warm socks and extra-thick pantyhose never make the to-do list. Many women think they can get by with their ordinary opaque tights and the no-show socks they wear with sneakers. If you wear a lot of midi skirts or sweaterdresses, swap your usual tights for fleece-lined ones, like J.Jill Fleece-Lined Tights in Black ($24, jjill.com) or Muk Luks Women’s Fleece-Lined Tights 2-Pack in Charcoal/Black ($20, macys.com); and your black leggings for fleecey ones, like Lane Bryant Fleece Lined Leggings in Black and Coffee ($22, lanebryant.com). The difference in texture won’t be discernible to anyone but you, and drafty rear ends and thighs will be history.

Socks are also a confusing category, with women asking whether to do a crew sock or a knee sock. If you’re wearing tall boots without tights or want extra warmth under wide-leg pants, opt for a higher sock, like Gap Women’s CashSoft Cable-Knit Knee-High Socks in Heather Gray or Modern Red ($12, gap.com), or Old Navy Women’s Knee-High Boot Socks in Blackjack or Heather Gray ($10, oldnavy.gap.com).

For every other winter shoe/boot sock situation, or if you can’t stand the calf compression of a tall sock, choose a crew length, like Gold Toe Women’s 6-Pack Ribbed Crew Socks ($15, kohls.com), a cotton/polyester blend in a range of light to dark neutrals; or, for a splurge, J.Crew Women’s Cashmere Blend Trouser Socks in Black or Radiant Ruby ($37, jcrew.com). What’s the difference between crew socks and trouser socks? Both hover at the lower calf, give or take an inch, but crews are often more casual, thicker or ribbed, while trouser socks tend to be silkier and dressier in texture. Once again, follow the coat/hat/scarf color strategy. Neutrals will give you the most polished effect, whether you match or tone the socks to your shoes and/or pants, but red never fails for a pop-of-color statement.

a collage with three different styles of waterproof womens handbags
(From left) Gap Factory GapFit Nylon Cross-Body Bag in Black; FLX Women’s Quilted Flap Crossbody Bag in Black; Quince Revive Nylon Crescent Shoulder Bag in Olive.
AARP (Gap Factory, Kohl’s, Quince)

6. A  no-slip, hands-free, rain-resistant bag.

 You have a fabulous leather or suede shoulder bag that’s absolutely perfect. It holds all your stuff, is totally organized with perfect pockets for keys, breath mints, your phone and sunglasses, and it’s ready to go. Is this the bag you want to wreck when it rains or snows? Does it slip right off your puffer shoulder and not have an adjustable or extra crossbody strap? If your favorite bag is a tote, does it leave you hands-free in icy, rainy weather when holding on to a railing might be a good idea?

My advice is not to give up your “good” bag, but do yourself a favor and get a weather-busting backup. A water-resistant nylon crossbody with an adjustable flat strap, like the streamlined Quince Revive Nylon Crescent Shoulder Bag in Olive, Ash Gray or Black ($29, quince.com); the Gap Factory GapFit Nylon Cross-Body Bag in Black ($16, gapfactory.com); the quilted FLX Women’s Quilted Flap Crossbody Bag in Black ($24, kohls.com); and the MZ Wallace Small Sutton Deluxe Tote in Black or Buff ($245-$265, nordstrom.com) will save the day. Black is what you want here. It goes with every coat and never shows stains.

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