Holiday lights are up, snow is falling — this is one of my favorite times of year. I love to dress up just because, and the start of winter means it's time to have fun with holiday dressing [1]. It also marks the beginning of the season for plaids, checks, and flannels! There's red-and-black buffalo plaid, the rich green and blue of black watch tartan — I even extend my appreciation into summer with madras! Yes, I'm mad about plaid; the chic heritage looks are effortlessly stylish and, at the same time, rugged. I love seeing holiday cards with families decked out in plaid pajamas. Whether it's great skirts or charming toddler jackets, Gap has a huge selection of plaid styles and great deals for the family. But plaid isn't just for the holidays; a great flannel shirt carries you right through spring! Even better, the more you wear it, the softer it is when it's broken in.
Right now, Gap is offering 50 percent off of outerwear, an extra 50 percent off of sale styles with the code BIGSALE, and an extra 20 percent off with the code ADDON. Order today to arrive before Christmas for last-minute gifting solutions!
Plaids to Cozy Up To
Keep scrolling for plaids to cozy up to from head to toe and great deals you'll be excited about.
Gap Adult Contour Mask With Filter Pocket (3-Pack)
An easy stocking stuffer that everyone could use, we love the checks on the Gap Adult Contour Mask With Filter Pocket (3-Pack) [3] ($5, originally $18).
Gap Grey Plaid Everyday Flannel Shirt
Pair this Gap Grey Plaid Everyday Flannel Shirt [4] ($40, originally $60) with a great pair of white jeans for a rugged winter-whites look!
Gap Red Tartan Everyday Flannel Shirt
This Gap Red Tartan Everyday Flannel Shirt [5] ($40, originally $60) is a classic for the holidays and beyond. We love this button-down with distressed blue jeans.
Gap Everyday Flannel Shirt
This Gap Everyday Flannel Shirt [6] ($40, originally $60) offers a softer colorway for this menswear look.
Gap Shirred Button-Front Shirt
This Gap Shirred Button-Front Shirt [7] ($44, originally $55) is a perfect top to go under a camel blazer.
Gap Shirred Plaid Popover Top
Trust us, this soft Gap Shirred Plaid Popover Top [8] ($54, originally $60) is so cozy, it's soon to become your work-from-home favorite.
Gap Double-Breasted Blazer
This Gap Double-Breasted Blazer [9] ($134, originally $148) has a classic sportsman style. Wear it with jeans and a great pair of cowboy boots as a nod to Princess Diana's style [10].
Gap Plaid Wool Coat
This Gap Plaid Wool Coat [11] ($124, originally $248) is a heritage statement piece at such a great deal!
Gap Plaid Sherpa Jacket
Sherpa is all over this season. We love this printed Gap Plaid Sherpa Jacket [12] ($58, originally $98).
Gap Recycled Cozy Scarf
This Gap Recycled Cozy Scarf [13] ($20, originally $30) is the perfect stocking stuffer.
Gap Slim Ankle Plaid Pants
Were you loving Leti's style [14] on HBO's Lovecraft Country [15]? These Gap Slim Ankle Plaid Pants [16] ($47, originally $80) are something she'd pair with tennis shoes and a knit polo.
Gap Double-Breasted Blazer
This Gap Double-Breasted Blazer [17] ($74, originally $148) would look great over a little black dress.
Gap Cape Scarf
This Gap Cape Scarf [18] ($24, originally $50) is the most elegant "little thing to throw on"!
Gap Blackwatch Plaid Everyday Flannel Shirt
This Gap Blackwatch Plaid Everyday Flannel Shirt [19] ($26, originally $60) would look perfect paired with Gap velvet joggers. Sumptuous and regal, but comfy!
Gap Blue Window Pane Plaid Everyday Shirt
We love this Gap Blue Window Pane Plaid Everyday Shirt [20] ($26, originally $60). It's very girls-next-door cool. Couldn't you see Joey Potter wearing this on Dawson's Creek?
Gap Flannel PJ Set
Do you have Christmas morning PJs yet? This Gap Flannel PJ Set [21] ($34, originally $70) is a must!
Gap Maternity Midi Shirtdress
We love the stylish ease of this Gap Maternity Midi Shirtdress [22] ($41, originally $70).
Gap Baby Plaid Shirt
As promised, we have looks for the whole family. How cute is this Gap Baby Plaid Shirt [23] ($14, originally $25)?
Gap Toddler Double-Faced Shirt
This Gap Toddler Double-Faced Shirt [24] ($17, originally $30) is perfect with a great pair of khakis for your toddler.
Gap Smart Flannel Shirt
He'll love this Gap Smart Flannel Shirt [25] ($53, originally $60) for years to come.
Gap Pleated Midi Skirt
Pair this Gap Pleated Midi Skirt [26] ($63, originally $90) with a great pair of boots and a fair isle sweater.
Gap Denim Western Shirt
We love the rugged cowboy look of this Gap Denim Western Shirt [27] ($49, originally $70).
Gap Baby Plaid Bodysuit
Gift this cute Gap Baby Plaid Bodysuit [28] ($21, originally $25). It's perfect for spring!
Gap Flannel Shirt
This Gap Flannel Shirt [29] ($41, originally $60) is the perfect layering piece.
Gap Baby 3-in-1 One-Piece
This whole Gap Baby 3-in-1 One-Piece [30] ($21, originally $40) is a great gift. It's the perfect full outfit!
Gap Baby Plaid Flannel Shirt
This Gap Baby Plaid Flannel Shirt [31] ($14, originally $25) is perfect for Christmas Day brunch with the family.
Gap Baby Plaid Jacket
This Gap Baby Plaid Jacket [32] ($29, originally $58) is so chic! Pair it on your little one with white stockings and Mary Janes for a classic look.
Gap Toddler Plaid Skirt
Or mix and match plaids with this Gap Toddler Plaid Skirt [33] ($20, originally $35)!
Gap Flannel Pajama Shorts
These Gap Flannel Pajama Shorts [34] ($12, originally $25) are perfect for lounging around the house all year round.
Gap Toddler Plaid Bow Clip
Buy this Gap Toddler Plaid Bow Clip [35] ($5, originally $17), as it's perfect for spring!
Gap Kids Plaid Bow Tie
We love the buffalo plaid of this Gap Kids Plaid Bow Tie [36] ($9, originally $20). How dapper!
Gap Kids Plaid Wool Jacket
This Gap Kids Plaid Wool Jacket [37] ($54, originally $108) is perfect for weekend adventures. It's durable and stylish.
Gap Toddler Mix and Match Graphic Leggings
At home learning? Add a little fun to the "uniform" with these Gap Toddler Mix and Match Graphic Leggings [38] ($8, originally $17)!
Gap Kids Smocked Plaid Dress
This Gap Kids Smocked Plaid Dress [39] ($29, originally $50) reminds us of a cute American Girl doll.
Gap Baby Plaid Dress
Or this Gap Baby Plaid Dress [40] ($22, originally $35) version.
Gap BabyGap Disney Mickey Mouse PJ Set
Grab this Gap BabyGap Disney Mickey Mouse PJ Set [41] ($31, originally $35) for the Disney fans in your life.
Gap Flannel Shirt Jacket
We love this Gap Flannel Shirt Jacket [42] ($71, originally $80).
Gap 4.5" Box Plaid Boxers
These Gap 4.5" Box Plaid Boxers [43] ($8, originally $15) are on sale, so get them in a few colors!
Gap Toddler Recycled Plaid Gap Logo Hoodie
Gap logo gear is making a big comeback! Gift this Gap Toddler Recycled Plaid Gap Logo Hoodie [44] ($27, originally $35).
Gap Flannel Joggers
These Gap Flannel Joggers [45] ($31, originally $40) are the perfect loungewear that you can wear to run errands as well.
Gap Kids Plaid Shirt
Stock up on this Gap Kids Plaid Shirt [46] ($14, originally $30) while it's on sale!