Big & Tall Outfits That’ll Keep You Warm All Winter

Big & Tall Outfits That’ll Keep You Warm All Winter

The cold weather is on the way. But are you prepared with the right apparel and footwear? The fashion industry is becoming even more inclusive these days, meaning it’s easier than ever to look stylish if you wear big and tall while keeping warm. In case you need some tips for how to look and feel your best all winter long, we’ve created outfit ideas.

Sweatshirt + Joggers

Let’s start with a casual outfit that’ll keep you warm in the cold. If you’re hanging out with your buddies at a football game or running a quick errand around the corner, a sweatshirt and joggers will undoubtedly keep you warm, especially if they’re both lined with super-soft fleece. A sweatshirt and joggers offer laid-back coziness. Plus, you can wear this combination to the gym or while running outdoors. You can replace the sweatshirt with a hoodie if that’s more your style. As for your shoes, sneakers and sneaker boots will do, especially if they feature optimal traction for braving slick sidewalks or water-repellent technology. However, for extra snowy days, sturdy work boots are dependable, plus they add rugged flair to casual outfits.

Crew Neck Sweater + Button-Down Shirt + Jeans

A crew neck sweater styled with a shirt underneath with big and tall jeans is still in the realm of casual outfits, but definitely not as laid-back as a sweatshirt and joggers. This outfit is ideal for casual work environments, dates, or outings with your family. The most comfortable sweaters you can wear include cotton and wool (such as merino or cashmere). The shirt underneath adds a stylish accent. You can’t go wrong with solid shades for the sweater, but stripes and color blocking are popular designs if you want to make more of a statement.

In terms of jeans, there are various big and tall jeans to choose from, such as straight, slim, and relaxed fit. Blue and black jeans would more than likely match most of your sweaters. No one’s stopping you, though, from rocking white, red, or other colored jeans. For a rugged casual look, style your outfit with leather work boots. For a more polished look, slide into leather Chelsea, chukka, or brogue boots.

Fleece Jacket + Solid T-Shirt + Jeans

There’s nothing like a cozy fleece jacket in the wintertime to keep you warm. A fleece jacket exudes a streamlined look, and a solid T-shirt adds an additional layer of warmth. When paired with jeans, this outfit is ideal for casual outings or even work. You could also wear big and tall fleece jackets during a winter hike since they offer warmth without all the extra bulk of other outerwear (however, for really cold days, you might want to layer over another jacket or coat). You can find fleece jackets with a quarter-, half-, or full-zip front closure—choose the design that best fits your style. This outfit also pairs well with leather Chelsea, chukka, or brogue boots.

Flannel Shirt + Graphic T-Shirt + Jeans

If you really want to make a stylish statement, a flannel shirt plus a graphic T-shirt and jeans are the way to go. This outfit—paired with the right outerwear—will certainly keep you warm and stylish. Flannel shirts are fit for the cold weather, but especially when they’re layered with other apparel pieces. Flannel shirts are usually made of cotton or wool and are available in multiple colorways. If you really want to go for that layered look, wear a denim jacket over your flannel (maybe consider an additional outerwear layer for frigid days). Finally, match this outfit with sneakers or sneaker boots. Or style it with leather Chelsea, chukka, or brogue boots.

Long-Sleeved Polo Shirt + Cardigan + Khaki Pants

Now, we’re getting into outfits that are less casual than those previously mentioned. If you’re looking for a go-to winter-ready outfit for work, a long-sleeved polo shirt plus a cardigan and khaki pants will keep your office style in check. Just like short-sleeved polo shirts in the summer, there are various long-sleeved polos to choose from, such as solid neutral tops to polos with vertical stripes. You might as well stock up on as many as possible! A comfortable cardigan will add a polished touch to your polos. You probably already have a pair of reliable khaki pants that you wear during the summer seasons—those same pair of pants will work just fine in the wintertime.

In terms of shoes, you can continue wearing your loafers and dress shoes. However, for snowy and wet days, you might want to wear a solid pair of men's winter boots—just switch into your office-ready footwear when the time comes.

Dress Shirt + Sweater Vest + Suit Jacket and Pants

Finally, this outfit is as formal as it gets. If you’re heading off to a special event, such as a holiday party or winter wedding, this cold-weather-ready outfit will keep you looking sharp. Start with a dress shirt—perhaps stick to a neutral tone that’ll blend in any environment. Then, style a cozy big and tall sweater vest over your base shirt. Finish off the look with a suit jacket and pants. A classic pair of leather brogue or Chelsea boots will match well with a suit outfit during the wintertime.

Pick the Right Outerwear for the Occasion

The right jacket or coat can take an outfit to the next level. For casual outfits, a parka, duffle coat, or puffer coat will all add a stylish layer. As for more polished outfits, pick out a wool peacoat or overcoat to wear. Once you’re done layering your casual or formal cold-weather-ready outfits, finish off by choosing the right winter accessories. Survive the winter months looking your absolute best—in cold-weather-ready apparel and shoes that’ll keep you as warm as possible.

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