When it comes to fashion, I am very good at staying in my lane. I learned this the hard way during a closet cleanse last year: When I purged my wardrobe with the help of an expert, it came to my attention that I was intensely loyal to A-line dresses. (She counted close to 50 of the same style, eep!) I also apparently have an aversion to work-appropriate tops, because I own exactly zero of them.

Post-cleanse, I internalized a new set of self-imposed sartorial marching orders. For one thing, I needed to re-train my brain to walk in the opposite direction of styles I already own in abundance (ahem, A-line dresses). But I also needed to practice getting outside my fashion comfort zone by seeking out new and fresh silhouettes that could help me not only modernize my look but evolve it, too.

So, I called in another expert: the queen of PureWow fashion, Dena Silver (she’s the fashion editor here). We set our sights on Zara, a store known for its relatively affordable mix of trendy and classic pieces. We also set what felt like a reasonable budget: I had $250 to spend on this shopping spree—I used it as a chance to liven up my wardrobe for fall. Dena’s main job? To select pieces I wouldn’t normally consider—then send me off into the wild (i.e., my apartment) where I would test-drive each piece and mix and match it with items already in my closet.

To document the experience, I called on my dear friend Ana Gambuto, a New York-based lifestyle photographer with a talent for beautiful images that capture the moment—and the mood of her subjects.

At the end of my shopping spree with Dena, we spent $259 total. (Pretty spot-on with our target budget, I’d say.) Here’s how each look made me feel, plus which looks I decided to return and which ones I kept.

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Outfit #1: Pleated Skirt + Oversize Sweater

The Shopping Experience: When Dena and I first walked into Zara, her hand skimmed this skirt. My reaction: “I have hips, so that style probably won’t work.” I’m also short—just 5’2”—so my gut instinct was that this was an item I would absolutely put back. She encouraged me to give it a try. “Pair it with something easy, like a sweater or a graphic tee,” she encouraged. That’s just what I did, pulling out an oversize pink Everlane sweater to balance the black and give the look a pop of color. I also slipped on a pair of studded heels (although Dena mentioned that a knee-high boot would also work).

The At-Home Verdict: I loved this skirt. Not only was it flattering; the midi length actually worked with my height. The crease of the pleats, which were sturdier than I expected, also meant that I didn’t get any lumpy spots in the fabric over my hips—a win. I gave the sweater a French tuck and it felt effortless, which is all I ever want from my clothes.

Total Spent: $39.90

Get the look: Zara skirt ($40); Everlane sweater ($95); Sézane heels ($225)

Outfit #2: Puffy Sleeved T-Shirt + Cropped Pants

The Shopping Experience: When Dena first showed me this top, it was impossible not to think of Seinfeld. Specifically, that episode when Kramer pressures Jerry to don what was certain to be the trend of the '90s: the puffy shirt. But I trust Dena's expertise, of course—she also assured me puffy sleeves are really and truly going to be big (pun intended) for fall. Another piece she plucked from the rack that goes against every style impulse I have: pants. I have plenty of denim in my closet, but more structured trousers, especially a pair that’s cropped, felt like a bold choice.

The At-Home Verdict: In the comfort of my own bedroom, I was surprised by my own reflection. First, the top. The delicate structure of the sleeves gave me instant polish. In my head, I thought I’d look like a football player, but once it was on, it was the opposite: I felt feminine and chic. As for the pants, I loved the length and the extra-wide hem. As an outfit, it looked great, but I kept pulling at the ripple effect by my waist and thighs. A sizing issue? Perhaps. But the constant fiddling and adjustments gave me a bit of pause here.

Total Spent: $79.80

Get the look: Zara shirt ($30); pants ($50); Birdie’s slippers ($95)

Outfit #3: Ruffled Floral Print Dress

The Shopping Experience: While wandering through the racks, Dena set my sights on another style goal: “Do you have any special occasions coming up?” My September birthday immediately crossed my mind. It’s not that you have to have a list while you shop but having a loose idea of events where you might need an outfit can help you prioritize the items in your cart, she explained.

The At-Home Verdict: This dress felt like the right balance of formal and relaxed. It also had a lot of details that were out of my wheelhouse: For one thing, it had keyhole sleeves (which, let me tell you, were a bit of a trial to get on correctly). It also had a slit that hit above the knee, a sexy detail that I was actually into. What looked like had the potential to be a totally busy pattern actually had an elegant and subtle effect once I tried it on. The pops of dark florals hit at all the right spots, making the overall effect very slimming. I also loved the peplum waist. I’m a new(ish) mom and that flourish made me feel so much more confident about my postpartum body.

Total Spent: $69.90

Get the look: Zara dress ($70); Sézane heels ($225)

Outfit #4: Floral Print Dress

The Shopping Experience: When Dena first added this to my cart, I immediately thought: This is a dress for cool girl moms—i.e., the kind that frolic around hilly Malibu on Instagram. I was certain the loose-fitting waist would swallow me whole. The whole thing just felt a bit too billowy for a petite person to pull off.

The At-Home Verdict: I was wrong. This dress is my favorite, and not only that, it’s the perfect transitional piece to take me from end of summer to fall. (Just picture it with a pair of brown boots.) Details worth calling out: The material doesn’t wrinkle (!!!!); the drop waist is loose, yes, but totally comfortable; the long sleeves make it a one-and-done ensemble, which means I can be dressed and out the door in no time at all.

Total Spent: $69.90

Get the look: Zara dress ($70); Madewell sandals ($128)

What I Kept and Returned

Bravo, Dena! I kept 60 percent of what I bought. I returned the pants—not because of the style but because of the fit. I’m now on the hunt for a cropped style that works better around my middle and comes in a darker, more kid-friendly shade. (Seriously, my son, pictured above, gets his food-covered hands on everything.) I also returned the short-sleeve ruffled floral print dress, but that was mainly due to the fact that I love, love, loved the second floral option. I’m trying to really nitpick my closet, remember? I don’t want to buy repeat styles right now if I can avoid it. And that puff-sleeve shirt? Well, it’s now in regular rotation for my weekday wardrobe.

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