What To Buy At the Gap Sale

Through this weekend, Gap is having up to 50% off everything, and then an additional 20% off your order with the promo code CHEERS. Not only that, this is GapCash time, so you will earn GapCash to use closer to the holidays. Reader Kim asked me to share what I think are the best buys during this Gap Sale, my picks are below.

Gap Crazy Stripe

I shared the Gap Crazy Stripe on Facebook yesterday. This is such a fun stripe, festive without screaming a specific holiday, a fun look for holiday photos, and a great gift.  The classic crew sweater is awesome, it comes in sizes for women (with tall and petite options), girls, and toddlers. I got me and Emerson matching ones, I sized up for her so hopefully we can still wear them together next year too.  Is a dress more your thing?  Again they have one for toddlers, girls, and adults.  Want your pup in on the Crazy Stripe action? Here you go!  I bought this scarf for Karl; it may be categorized for women but the men's Crazy Stripe pieces aren't the same color combo and I think it looks relatively gender neutral.  Same goes for the beanie, it could be worn by anyone.  Some other cute Crazy Stripe pieces are the Crazy Stripe slipper for women, the cutest headband with pomp pom “ears”, adorable booties for little ones, and these gloves that will slide up under your coat to keep your wrists warm.  Speaking of warm, it's ridiculous but I adore this Crazy Stripe union suit, and the sweater leggings for girls, toddlers, and women would make for cozy loungewear with the matching sweater.  Now I want to get the leggings for me and Emerson… this is the dangerous part of writing these sale posts for you – I want it all!

Festive Fashion

‘Tis the season to be jolly… and sparkly.  Whether it's a cookie exchange in your office lunchroom or a black tie gala at a hotel ballroom, likely there's a situation coming up in the next several weeks where you need to look festive.  Gap's fit can be hit or miss, but these are the pieces that look the best IMO:

  • This foil cable knit sweater is traditional with a touch of sparkle. Pair with jeans for a GTG at your best friend's house, or up the festive factor with a red pencil skirt or ankle pants for the office happy hour.  A sweater like this can also go glam, style with a pencil skirt like this one from Gap for classic meets disco ball style or consider pairing it with a midi-length or ballgown-length black taffeta skirt and a pair of jet bead earrings.  Available in tall, regular, and petite.
  • I‘ve always been a fan of a sequined t-shirt style shift dress.  All the comfort of a relaxed fit, but super glam.  Wear for the office holiday party at the restaurant down the street with black tights and ankle boots.  Come New Year's Eve pair with silver heeled sandals and dance into 2018 in style.  In silver, this dress isn't stuck to the winter months; you can wear a dress like this year-round if the situation is right!
  • Velvet is a hot trend this season, and a way to look luxe without spending a pretty penny.  Even better, most velvet is stretchy so you can have that extra canapés or cocktail.  This velvet short sleeved tee is a great wardrobe addition.  Wear with dark jeans, heels, and a sparkly statement necklace for a night out.  Style it with a sequined pencil skirt and heels for a cocktail party, wear with velvet pants for a restroom-friendly jumpsuit (these joggers also from Gap would be a cool pairing and look great with pointed toe flats in leather or some sparkly confection).  Or consider a skirt like this velvet wrap skirt from Gap to create a dress effect but have two awesome separates to style in different ways (the skirt would look gorgeous with a turtleneck sweater or even a denim shirt!).
  • A party top is always a smart closet addition.  Style with black pants or a pair of jeans and you're ready to hit the town!  Gap has several this season that look appealing.  This long sleeve sequin top is spectacular (and omigosh pair it with the matching pencil skirt for an ultra-glam look that provides a more custom fit than a single dress and more styling options!).
  • Just want a touch of casual glam to pieces already in your closet?  How about a kimono? This velvet kimono comes in two colors and looks so rich.
  • This blouse isn't shiny or glitzy, but the red color and the details like embroidery and puffed sleeves makes it festive.  Style with black velvet ankle pants and D'Orsay pumps, or even with a pair of jeans and ankle boots.

What to buy during the Gap Sale

Jackets and Coats

Gap does cool jackets and outerwear really well.  I have Gap jackets that are decades old and they have a perennial cool style that transcends trends and I find to be pretty versatile with a variety of personal styles.


Jeans are a personal decision.  What works for one doesn't always work for another.  However, I've had a lot of luck with Gap jeans over the years and I know a lot of you have figures similar to mine.  If I were shopping for jeans right now from Gap I'd be heading to their Real Straight Jeans which are a fave of mine.  I have these Mid Rise Classic Straight Jeans and they are a nice basic that looks classic and clean.  No frills, nothing to make them look cheap or too trendy.  I buy the short length for regular, it fits better for a curvy bum than petite.  My grey jeans are from Gap and getting threadbare; these high rise slim straight fit jeans look like a nice replacement pair.  As I mentioned, velvet is a hot trend this season but it doesn't have to be just for evening wear.  A pair of velvet jeans are a fun alternative to corduroy.  I‘m loving these velvet skinny ankle pants (they look more like jeans but Gap calls them pants) and they come in five fantastic colors.


Some items caught my eye and they just don't fit in a category.  Like this loop-fringe block cardigan that would look amazing with the velvet jeans in the same French vanilla ice cream color.  Or this hooded sweatshirt with a badass tiger graphic on it that channels Gucci without the insane price tag.  And the whole Softspun collection.  I have a dress from it and it is a fave; their winter pieces in this super soft lovely washable fabric look like the best loungewear ever and many pieces are quite appropriate for brunch, errand running, or even a casual office.

Do know this isn't all that is great at Gap.  I focused on street wear and didn't even delve into their amazing activewear or their sleepwear/intimates.  I've found their accessories and pants to be hit or miss; if you like them it's worth a gander because there's some gorgeous looking pieces.  And of course, Gap is great for babies, kids, and men (I love that they have tall options for Karl).  Let me know if you score any good deals at Gap this weekend!

FYI I tried to create collages of images for all the categories but I'm working for one of the first times on a Mac and I was STRUGGLING with PicMonkey and Gap's images acting weird.  I also had trouble grabbing Gap images for the collage I shared on Facebook and now I can't get it on this computer.  Give me a bit of time, I hear you and will try to have images in future sale roundups!


  1. Stacie Scattergood
    November 14, 2017 / 11:45 pm

    Oh that band jacket. So Beatles/David Bowie.

  2. Michelle Van Ellis
    November 12, 2017 / 8:16 am

    Ahh! That gold sherpa jacket! Thank goodness they don’t have plus sizes. I just saved $200!

  3. Anonymous
    November 11, 2017 / 8:59 pm

    I stopped in Gap today and got an extra 40% off coupon but I ultimately did not use it. I am not thrilled with their clothes anymore, although the baby/kids stuff is cute. They charge way too much for low quality goods. They did have a cute pair of pajama pants with skiers on it but then I asked myself: do I really need another pair of pajama pants? Plus, the pant legs were so wide. Gap used to be so good and it is really a shame. Uniqlo is now my go to store for quality basics.

    • November 14, 2017 / 3:31 pm

      I wish Uniqlo had a larger size range I’d feature them more often. But I don’t fit in their clothes so I don’t feel right promoting them if I can’t vouch for them. But I hear you on Gap, they used to be a go-to for great basics but seem to have lost their way. I still find some real gems there but it’s not as easy as it used to be.

  4. DC Celine
    November 11, 2017 / 4:59 pm

    Stop it. Too many good recommendations! And you know I follow yours. That being said, the sequined pencil might be just the thing (BELOW THE KNEE!), I need new classic jeans, and I do love their crewneck!

    • November 14, 2017 / 3:29 pm

      I think a sequined pencil skirt is such a smart purchase. With a silk blouse, a cashmere turtleneck or crewneck, a band tee and a pair of booties, a velvet blazer and ruffled blouse… I could go on and on!

  5. Leslie Beard
    November 11, 2017 / 3:10 pm

    Regarding the $560 leather jacket: one way to motivate yourself to remain the same size or close as years go by is to buy something this expensive and not want to waste the money by “outgrowing” it. I have an alpaca coat that I hope to wear forever. Given what I paid, it will be years before I feel I had my money’s worth out of it. That is thing with coats (and purses and watches)–we wear these things A LOT, and so I think they are worth a splurge. The cost per wear may be lower than that of less expensive but less worn garments.

    • November 14, 2017 / 3:29 pm

      That is SUCH a good point Leslie! I think of some of my priciest pieces in my closet, they are ones I wear regularly, and look forward to re-wearing making the cost per wear far less!

  6. Kim
    November 11, 2017 / 10:53 am

    I am the one who requested this on FB — I feel so special. I’m going to get the Vince-like coat. I live in the Bay Area so it’ll be perfect. Also just noticed ebates for Gap is at 11% for even MORE savings. Thanks! I think your full time blogging will be great for my wardrobe. 🙂

    • November 11, 2017 / 11:08 am

      Aaah that coat is divine! I hope it’s fantastic on you! And thank you for the suggestion. Posts like these are time consuming but they’re also fun and a bit meditative and you caught me at the perfect time (and it was a good test for me to get used to blogging on a Mac!)

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