As an editor at Who What Wear, I should really be well-versed in the sartorial options available at Amazon… but I’ll just be honest: I’ve never bought clothes from the site before. And since the retailer’s strong assortment of brands (and deals) is a constant topic at work, I knew I needed to change that. But it’s a big site, and I had no idea where to begin, so I turned to the girl who’s always shown me the way since we met in seventh grade.

My best friend Alex is a clinical social worker at Bellevue Hospital’s Program for Survivors of Torture in New York, and when she’s not meeting with her clients there, she’s running a private therapy practice at her home. Did you just scroll up and scroll back down to read that right? Yeah, social workers don’t look like they used to! The point is, she doesn’t have a ton of free time. But as a stylish woman, she still wants to shop and look good for herself, so she often turns to Amazon to update her wardrobe on the quick. Her advice to me? Know your brands and the look you’re going for, then read the reviews. So I took her advice and browsed the list of brands available on the site: I instantly recognized names she mentioned were solid—The Drop, Astr the Label, Daily Ritual—and stumbled upon even more I already know and love, from Staud and Sam Edelman to Free People. From there, Amazon kept leading me to similar brands I’d never worn before but always hear my co-workers talk about: Line & Dot, Lioness, LNA, to name a few. Alex told me I was overthinking it, and well, she was right. I ended up with so many items in my cart, I have to send a bunch to her because my closet can’t handle this many new purchases. Curious to see all my amazing finds from my first Amazon swoop? Keep scrolling for pieces I want for myself and ones I know Alex would love, too.

Everyone needs an oversize blazer in their wardrobe. It’s a nonnegotiable staple.

I see second skins everywhere I look these days. It’s time to get my hands on at least one.

Another winter trend I’ve had my eye on. I think this is the workwear jacket for me.

The top for all my Zoom holiday parties.

Everyone needs a fun and colorful sherpa in their loungewear rotation right now.

A small cardi may be the most versatile thing you can buy.

I love a warm-colored oversize coat for the winter months. It feels more unexpected than black and goes with everything.

I love the way Alex layers her gold jewelry with the coin pendant and chunky chain necklaces. This mosaic coin feels like something I’d wear, layered or not.

But I’m obviously going to follow her lead and layer it up.

I love a mesh top. I always feel confident, edgy, and a little unexpected when I wear a top like this. That square-neckline doesn’t hurt either.

I live in high-waist rigid denim, and I need a pair in this colorway.

Alex and I are both Bay Area girls, so we’ve already lived the Doc Martins trend. While we will always love the classic, I think I can speak for both of us when I say it’s time for a fresh spin on the combat boot.

You can’t have enough black mock-neck sweaters in winter. It’s a fact.

The perfect WFH dress.

Actually, you can’t have enough mock-neck sweaters in any hue.

I know if Alex and I were still roommates we’d share these joggers.

This dress hits every important styling note of 2020: square necks, tiered midi skirt, and delicate eyelet fabric.

Quilted coats have such an understated, chic quality to them.

I know I have another sherpa jacket on this list, but this bomber style is so cute, and I feel like would make an amazing thank-you gift to Alex. She needs proof I listened to her advice, after all.

Chunky oxfords are the way to add a cool-girl edge to any outfit. You think it’s a pair of lug-sole boots, but I promise these do the trick as well.

That ribbed knit has made its way to sweatpants is the 2020 win we all need to celebrate.

You say summer dress; I saw throw that black second-skin top from earlier underneath this dress with a pair of tights and combat boots, and you actually have a really cute winter look.

I really do like a tiered midi skirt. What else can I say?

I can’t even believe this isn’t sold out.

I’ve been looking for the perfect acid-wash jeans for too long.

It would not be an Alex-inspired style guide without a pair of gold hoops. I opted for a smaller pair for myself because we’d all have a laugh if I threw on a pair of large hoops.

For too many years, Alex has pushed me to wear sweater dresses that hug my body, and I think I’m finally ready.

I can’t look at these and not see my best friend.

Paperbag pants are the secret looking put-together while dressing comfortably. And they look really good with a pair of ankle boots like the ones above.

I couldn’t be happier puffer jackets are back in style because they’re the only thing that actually keeps me warm when it’s cold out.

The exact top I’d throw on any day of the week. Pair with jeans, leggings, sweats—you name it.

I don’t know about you, but I’m in California, so buying another pair of biker shorts in the middle of the winter isn’t that crazy.

That doesn’t mean I’d say no to the perfect pair of black leggings though.

Everyone has their go-to white sneaker, and the classic Superga Cotu is mine.

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