25 Fall Items That Put a Smile on My Face

A post full of pick-me-ups.

Shop With WWW, our annual two-day shopping event, is here! Between now and 11:59 p.m. PT on October 22, you get to shop with exclusive discounts from our favorite brands and retailers. Be sure to visit our event page to browse all the incredible deals on offer. Happy shopping! Shopping makes me happy. Shopping makes me smile. There I said it! I must not be the only one who is a little too dependent on their mail carrier for a mood boost am I? If you’re in the “looking for any excuse to smile” club with me, join me on a little shopping excursion in the form of a slideshow of happy picks. And since my shopping has taken a turn for the slightly more practical with a longevity-focused bent, I picked items that are lovely and special, but not over-the-top trendy or kitschy. Sorry, no tie-dye in this roundup! And since the Shop With WWW event I mentioned above is going on right this second, all the picks happen to be on sale—just use the code AFFIRMWWW at checkout for the discount. Take a scroll and get ready for a smile.

In my mind, hat-wearing people are fun people who are not afraid of pulling off a look. This fall, I’m calling all that hat-wearing energy in. 

Oh baby, these buttons. These buttons are doing it for me! On that little diagonal? Perfection!

At first glance, she may not seem so special, but take a closer look. Is this not the perfect never-take-it-off chain? It’s beyond effortless. 

All summer long, all the fashion people have been wearing these lightweight rubber slide-on sandals. I think they’re on to something, so this fall I’m adopting the comfort shoe with a chic ribbed sock. 

Shop the matching Terry Shorts ($51). Verishop deal: 20% off full-price fashion with a $75 order minimum. The fervor induced by a beautiful set has not left the building. Get. This. On. My. Body! 

In case you also overbought into the floral mask category this spring and summer (ahem, just me?), here is a delightful palate-cleansing trio for fall. I like the neutral colors (no mask-outfit-matching anxiety), and the little pop with the coral ear loops. 

Click this link to apply a 10% off site-wide code. My word, these boots are gorgeous. I know, I know, the black would be more practical. But when you’ve got a 1” lift off the ground, you’re a little more protected from scuffs and dirt, no? And you can’t beat the wow factor that comes from the eye-catching white color. 

Long-sleeved terry in the summer sounds a little hot, so I’m going all in on this darling set for fall. It will be perfect for pretending that I play tennis.

Ya’ll know chocolate brown is where it’s at, right? The color is all that matters right now, and this easy dress is the pick of the litter. Those sleeves are a special touch, and I love the ruching at the bust, too. Hello, Thanksgiving outfit! 

Click this link to apply a 10% off site-wide code. I want to stack all of these gorgeous rings on one finger until I can’t move my knuckle. But if I had to choose one, I’d go for the green. 

There’s something deliciously retro about these sneakers. Imagine them with a bright yellow sock. 

Click this link to apply a 10% off site-wide code. Please note the special little v seam right at the base of the turtleneck. This little seam has my heart, and the whole sexy open back situation just sealed the deal. 

You didn’t think I was done with sets did you? This little floral trio in perfect fall shades is exceptional. I can also vouch that Le Set’s lounge separates are supremely soft.

A mismatched earring is fun! A mismatched earring makes me smile! Pearls and cloisonné. What more could you want?

How can you fault this bag? It is timeless. It is understated luxury. It is 30% off for just two days. Don’t delay, my stylish friend!

There is nothing that says expensive like a tennis necklace or bracelet. I also enjoy that Stone & Strand is fine jewelry (a.k.a. you are buying a family heirloom) without the markup that’s common in the diamond industry.

A string of baby pearls with a big drop pearl at the center? Good gorgeous, this necklace is stunning. I can feel your next Zoom compliment coming… 

A blazer coat is always chic, and always in style. I think this one is particularly special because the brown and black check makes it just as easy to wear with either neutral. This is one you’ll have for years to come. 

I own these bangles, and a) enjoy how they look more chic than your average wrist and ankle weights and b) appreciate how if I’ve made the darn effort to workout, these bangles will make sure my time is worth it. 

This plaid top is styled in a rather summer-ready way, but I see this easy, alluring top as a perfect fall pick. Just picture it under a shearling coat with your easiest jeans.

Soft pants! Two words that have become very important to me over the last several months. These are a super easy oat color, and I swear would look borderline polished with a tee and a blazer on top.

There’s something about a fresh pair of sneakers that just makes me smile. I always spring for white season after season and get bummed when they start looking dingy. This fall, I’m one step ahead with this dreamy cloud gray that is sure to last longer. Next up, check out the pretty face mask trends to know before your next re-stock.