I Faced Down My Biggest Fashion Fears, From ‘Ugly Shoes’ To Sheer Skirts

Here’s what I learned.

reformation cargo pants

The fluidity of fashion is what makes it fun — and keeps us on our toes. Yet, because trends come in waves, it can be hard to decide which ones are worth investing in and which to skip. Personally, I’ve always stuck to the basics. If you took a look at my wardrobe, you’d be surprised at how many different variations of the same button-down, tank top, and vintage jeans I have smushed into my extra-small NYC closet. These staple garments feel easy-to-wear and are guaranteed to look good together; that way I never have to worry about not having an outfit. But, as I walk around the New York City streets or peruse my daily Instagram feed, I always find myself envious of more adventurous women confidently boasting the fashion trends dominating 2022 — sheer garments and cargo pants, for instance, have been all over the city’s street style scene lately.

As I’ve begun to focus on what’s buzzy amongst those in the know, I’ve found that there’s a disconnect between what I want to wear and what I’m actually wearing. For example, I wind down at nights by scrolling through my favorite retail sites (we all have different guilty pleasures!) and curating a cart filled with on-trend, sometimes over-the-top garments. Then, just as I get out my credit card to click purchase, I abandon my mission because I simply can’t imagine wearing the pieces IRL. To scratch that shopping itch, I’ll then turn to my go-to sites and add yet another button-down to my wardrobe and think: Maybe getting it in stripes will spice things up?

But, as of late, 2022’s fashion trends have been tempting me more than ever before — all the see-through garments, quirky shoes, and retro-inspired accessories are just calling my name. So I decided to take on a challenge: wear buzzy pieces in public, one item per day for a week, and see what happens when I step outside my comfort zone. Join me on my journey ahead!

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Day One: Retro Sunglasses

After being out of town for a week, I made plans with my 22-year-old sister and her best friend to grab drinks and dinner — we had lots to catch up on, of course. I decided this meal would be the perfect opportunity to start my challenge as Gen Z girls are probably the least likely people to judge me for wearing retro, alien-like sunglasses.

Trying on my shades from Lexxola, I felt like the only way I’d be able to wear them in public would be to channel my style icon Hailey Bieber; she’s been known to sport a sleek pair when strutting around NYC. I decided to copy her formula of an oversized blazer and neutral hues so my eyewear would have ample opportunity to shine. But as I slipped into my black Zara blazer and Mango tube dress, I started to get nervous. I thought “this isn’t me” and my stomach was in knots (maybe dramatic, but this look felt like I was diving into the deep end.)

My solution? I Facetimed the girls to get some much needed support and they told me I had to do a slicked back bun to get the full street style look. I agreed. They guided me on how to do it (the key is lots and lots of hair gel) and I was ready for my photo-op. Luckily, I had the shades to make me feel a bit less naked, as they shielded my eyes and drew the attention away from the unfamiliar hairstyle. I looked in the mirror and thought, “who is she?!” But at the same time, I felt like I’d be making Mrs. Bieber very proud.

My Takeaway: If you’re trying out something new, go into it by channeling someone whose style you admire (for me, of course, that was Hailey Bieber). Even if you’re not someone who typically dresses similar to that celeb or influencer, tell yourself you’re going to try out your own version of their look. That way, if it doesn’t feel comfortable for you, it’s not your style — its theirs.

Day Two: Cargo Pants

Bella Hadid, Emily Ratajkowski, and Kendall Jenner have all worn cargo pants lately, making them one of the buzziest pant styles for 2022. The garment has received a bad rap, though, as they are typically associated with putting function above fashion. But recently, pants covered with pockets have become a staple for celebs and, IMO, they’re a playful and quirky way to spice up your bottom collection. Honestly, this style felt the least intimidating for me as Reformation had a pair that felt like the balance between full-on cargo and denim — so thank you, Ref!

As I ran out for an afternoon caffeine pick-me-up, I reached for my new cargo jeans and styled them how I would for a normal afternoon in the neighborhood. On top, I wore a graphic baby tee (it’s actually from Reformation, too) that showed just a bit of my stomach since the pants were mid-rise. Then, I kept with the edgy feel by completing the look with my white Classic Old Skool Vans.

My Takeaway: Ease into trend-driven garments by finding options that don’t feel too far from your normal. If you’re looking to style cargo pants for the first time, try a denim pair (like mine) or a pair of sleek trouser-style pants to help get the look without making too big of a commitment.

Day Three: Sheer Skirt

When I saw Kate Moss’s iconic metallic see-through dress from the ‘90s, I immediately became obsessed with the sheer trend. What I love about see-through garments is that they reflect major confidence. But, as much as I admire when other women wear transparent pieces, I’ve always felt like they were just too much for me to try. Of course, this hesitation is what prompted me to go all in for this challenge.

I decided I’d go with a sheer skirt as inspired by fashion editor Laura Reilly, who wore a bright orange sheer skirt with a plain tank top while on vacation. Her outfit was so good and relatively simple to recreate — so I decided to copy it for a beachside happy hour when headed out East to the Hamptons for a weekend with my family. Before leaving, I mustered up all my bravery and reached for my transparent, mesh midi skirt from Frankies Bikinis (which has a super cute sequin logo on the back). Underneath the statement piece, I wore a simple black thong from CUUP that gave me a bit of coverage thanks to the mid-rise silhouette. To finish the look, I went with my black Aritiza tank top, platform flip flops from mou, and carried my sparkly Frasier Sterling shoulder bag.

Did I feel naked (and every slight breeze)? Absolutely. Was my dad unhappy with me leaving the house like this? You bet. (I did it anyways in the name of journalism!) But, I was surprised at how confident I actually felt once I walked through the front door. “I’m really doing it,” I thought.

My Takeaway: Sometimes all you need is an inspo pic. Look for ideas on your favorite influencer’s Instagram feed or a dreamy Pinterest board. Once you’ve decided on what vibe you’re going for, use the photo as a roadmap — but don’t forget to add your own personal touches if you can.

Day Four: Clogs

For the fourth and final day of my styling challenge, I went for the chunky clogs — you’ll find similar pairs in the wardrobes of Kendall Jenner, Dakota Johnson, and Katie Holmes. What makes these “ugly” shoes so popular with celebs? I think it’s because they’re easy to slip into but feel elevated compared to a pair of simple sandals or slides. And while I typically stick to leather slides with a criss-cross vamp or my Birkenstocks, I loved my new chunky mules from Reike Nen, a South Korean brand that sells made-to-order footwear, from the get-go. I felt like the neutral tan color would fit right in with my relatively minimalistic wardrobe while still emanating a certain clunky-cool aesthetic.

When selecting the rest of my outfit, I considered the activity at hand — which in this case was heading out to the farm stand to pick up fresh fruits and veggies for the week. (I’m not sure the exact logic, but when I saw these shoes, I thought “these are farm-appropriate.”) To create the look, I kept things casual with my high-waist Paige denim shorts and a semi-sheer Zara crochet top with a CUUP bra underneath. Really, the shoes were the simplest part — I just slide into them and was off.

My Takeaway: Select your footwear based on the occasion, even if it’s something small. For me, I had to envision my new shoes in a place (the farm) in order to decide the best way to style them. By placing them within a vibe, I could then curate the rest of the outfit to match the mood of the outing.