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The New Jackie O.

5 Subscription Box Trials that Earn Southwest Airlines Points

Updated: Apr 25, 2018

Get the best subscription box discounts and earn airline points at the same time!



When a good friend announced they were getting married in another city, I said, "Fun - a weekend getaway with my best buds!" Know what isn't fun? Spending $450 on the hotel, $300 on a flight, $100 on a dress and knowing just how much our group will spend eating and drinking around town. As a Southwest Rapid Rewards credit card holder, I was about halfway to earning a free flight with my points. Rapid Rewards Shopping is the easiest way to earn quick points - and I fell head over heels for their subscription box offers. Not only do you get points, but you also get great sign-up deals*! So which boxes came out on top?


1. Gwynnie Bee - 2700 pts for signing up | 30-Day Free Trial

If you have never heard of Gwynnie Bee, it is a clothing subscription that allows you to rent clothing, wear it as long as you like and then send it back in a pre-paid return bag. Think Netflix DVD rentals - but for your wardrobe! Members build their own personal closet and GB sends you items from your digital closet. Pro: I loved ordering clothing, wearing it and not having to wash it before returning it! From size 0-24, there is a huge selection of work, evening and casual pieces to add to your wardrobe. Most tops and dresses that I added to my closet fit well. Bottoms were a little trickier, but no different than ordering any other jeans online. Con: You don't get to choose which items you receive. After adding about 20 items to your profile, clothing is sent out based on availability. It's a fun surprise, but can be difficult to get a specific piece.


2. Winc Wines - 1,400 pts for signing up | $20 off Your First Order

Specialist-chosen wines tailored to your personal taste profile - what's not to love? The box packaging from Winc was so cute and it was securely packed in there. Two bottles in the order were excellent, but the other two weren't memorable. Pro: While I didn't get much say in the wines I received, I liked that with every box order, my wine specialist is more likely to send wines I would like. Con: I usually spend $6-$8 per bottle of wine at Trader Joe's. The average bottle price for Winc was higher than I would usually spend, so this was a bit of an extravagant purchase past the initial first-order discount.


3. Bright Cellars - 12 pts / $1 spent | $30 off Your First Order

Bright Cellars is very similar to Winc, but with more flexibility on what you can order. Bright Cellars recommends wines, but allows you to choose your own if something in their collection strikes your fancy. Maybe you love red, but are hosting a girls' brunch and need a bubbly white? No problem! Pro: While a little more expensive, Bright Cellars runs all sorts of email promos for members that lower the overall price of being a member. Con: A little pricey. Also, if you love a particular wine, it may be sold out by the time you place your next order. The variety turn-over is a blessing and a curse.



4. Home Chef - 350 pts | $30 off your First Order | $10 off your Second Order

There are a few other dinner kit subscription boxes on the Southwest Rapid Rewards site that offer higher points (and I tried them), but Home Chef was the clear winner. While 350 pts may not sound like much, this was overall the best deal for a first box discount. I have to make dinner anyway, right? Pro: I consistently liked the large meal selection offered every week and the price point seemed really fair for what I was getting. I also felt the meal prep times and protein selection were fantastic. Con: By comparison to some of the other kits, Home Chef gives smaller carb portions of rice, pasta or potatoes (and this Midwest girl loves her carbs).


5. Stitch Fix - 400 pts | The $20 Fee Can Be Applied to Any Item Purchased

Stitch Fix is an inexpensive way to boost the points in your Southwest account. After filling out a style profile and creating a Pinterest inspiration board, a personal digital stylist will send you a five item box fashion box ($20). This has been hit-or-miss for me so far, but I love the idea!

Pro: If you have an upcoming event or need certain items (i.e. office attire or dresses for attending a wedding), this is painless way to shop. Returns are super easy. Con: Stitch Fix doesn't allow for much communication between you and the stylist. In my last box, I said in my note section that I was "backpacking through Europe" and my stylist thought I meant I was going camping. With more note space or communication, that could have been easily cleared up.


With so many different subscription boxes popping up every day, finding the best Rapid Rewards Shopping deals on airline points can be tough. This list is just a guide for which boxes worked best for me. Be sure to check out my website referral links for even more discounts, and download the Southwest Rapid Rewards Chrome Extension to learn which of your favorite sites already use SWRR. Happy shopping!


*The bonus points for Southwest Rapid Rewards Shopping sites are constantly changing, so be sure to check the site for current promotions.

What is on my Stitch Fix Pinterest Board?

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