Twenty bucks can go a long way. But can it buy a full outfit from a high-end clothing retailer?

On Thanksgiving eve, I ventured to the Macy’s at the Westfield Old Orchard mall with $20 in my pocket to find out if the feat could be done, and perhaps to succeed where former Sports Editor Greg Svirnovskiy had nobly failed. 

I set a couple of rules for my pursuit. One, I had to buy the outfit in the unfamiliar and expensive terrain of Macy’s. Two, I had to purchase both a shirt and a pair of pants. And three, the ’fit had to be as fly as me. 

Another motivation pulled at my proverbial strings. A couple days earlier, Ray O’Connell from athletic communications expressed his high hopes for my outfit at the Illinois-Northwestern football season finale, and I couldn’t let Ray down. With the stakes set, I strolled into Macy’s, the sweet symphonies of “An Evening with Silk Sonic” streaming through my AirPods. 

I brushed off the distractions of Macy’s red bows and ornaments and got to work in the men’s section. A Black Friday presale extended to most of the items, and suddenly, my outrageous goal seemed within reach. 

I sampled a black velvet jacket with gold accents for $25, then a baby blue zip-up hoodie on half-off sale for $37.50. Both were well over the price range, but feeling the soft textures and bold colors against my skin got me in the mood. Each would make a fine addition to my wardrobe collection, but rules are rules. I took brief trips to the athletics and suit sections — two low-risk, low-reward detours that fulfilled their purpose — refreshing my mind for another swoop.

Slowly but surely, I returned and worked the price down. My hands grazed the eclectic fabrics of a rack of $12 shirts. Any pair of chinos or formal pants would price me out of my budget, but pair a tee with some athletic shorts and maybe I could hit $20. 

Then, as I combed through the discount tees, I saw it. A “42 Wallaby Way Sydney Australia” shirt, replete with a glorious sunrise, Marlin and Dory from “Finding Nemo” and a comforting blue shade. I checked the size — medium. I’m in business.

The problem was that the price tag wasn’t there, so I proudly wheeled my treasure to the cashier stand. I handed it to the cashier, explaining the price tag situation, and she checked the computer. Minutes passed, her eyes darting across the screen and my heart palpitating. 

We made eye contact. This was normally a $28 shirt, she said, but with the sale it would be … $20.

Disaster. That meant the seemingly storewide half-off sale didn’t even apply, and there was no way I could pair this shirt with another item. The setback sent me into a frenzy, now battling against the limitations of my budget and the factor of time. I now only had 30 minutes before my movie, “House of Gucci,” started a couple stores down. 

I kicked my strategy into a higher gear. I planned to drop $12 for Champion shorts, leaving $8 for a top. 

A navy long-sleeve got me down to $10, but the fabric started shedding on my nice white turtleneck and felt more like a waffle than a waffle-patterned shirt. Worse, the shirt dislodged my AirPod when I tried to fit it over my big head, and I wasted precious time sprawled on the floor trying to find it. Fifteen minutes left. 

I spent a couple minutes trying on a $280 navy blue jacket in the mirror, a necessary distraction, then snapped back in. Ten minutes left.

With eight minutes left, I stopped to reassess. I wouldn’t find an outfit for less than 20 bucks. I wouldn’t find this AirPod. I wouldn’t make it on time to the movie. But I could still find a fit for the Illinois game, and I could still make Ray and The Daily proud. 

I brought the baby blue hoodie from the start of my visit to the register and coughed up $40 for it, then I threw it over my turtleneck during my stroll across the mall. Success evaded me, but that’s for the next sports editor to achieve. I came away with a sweet hoodie, and I even found my wayward AirPod when my turtleneck unwrapped. 

Minutes later, I strutted into Theater No. 2 to watch “House of Gucci,” proud and fashionably late.

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