Samantha Elise’s Weekly Attire Guide

Samantha Elise started sharing outfit photos on Instagram for fun while in high school in Missouri. People began to notice, and she’s now a stylist in Chicago. “I’m finally reaching a point where I can celebrate who I am and what I do,” she says. “It feels freeing.” Here, Samantha presents five outfits she donned over a week and discusses ballet, her experience growing up adopted, and tips for finding the ideal blazers…

Shirt: Everlane. Sweater: ASOS. Glasses: Jimmy Fairly. Watch: “hand-me-down from my mom.” Purse: vintage.

“I refer to this as my ‘no-hassle uniform.’ The jeans are relaxed, allowing me to enjoy meals without worry. It’s layered, so I can wear it in various settings, like a museum where the AC is cranked or with the sweater casually draped over my shoulders outdoors if it’s warmer.”

Vest: Madewell. Pants: Naked Wardrobe. Glasses: Jimmy Fairly.

“You can rock a vest alone or over a tee or turtleneck. Just experiment and enjoy the process of discovering what feels right. I don’t know anyone who curates their favorite outfits on the first attempt.”

“My sister designed this window tattoo. It represents my apartment in Boston, where I lived for six years while dancing at the Boston Ballet School. I practiced ballet from age three to 19. I adored it for a long time, but transitioning from local performances to dancing for a company was surreal. It resembles the media’s depiction — intense and competitive. The atmosphere felt akin to Black Swan.”

“I was in a leotard for eight hours a day, six days a week. I only wore regular clothes on Sundays, my day off. I’d assemble outfits and go people-watching. Boston boasts numerous colleges, so I’d encounter fascinating, inspiring streetwear. I also noticed people in exquisite office attire, like stunning suits and dresses. It felt so unlike St. Louis, where outfits skewed towards comfort, like sweatpants and Uggs.”

Tank: Madewell. Skirt: Madewell.

“I’m adopted, and as a child, I often pondered my identity. My entire family is white, except for my other adopted sister who’s Black and Puerto Rican. Ballet is predominantly a white environment — I was the only Black girl during my time at the Boston Ballet School. For a long time, I was quite reserved because I struggled to locate my place. Yet, I consistently conveyed myself through clothing.”

“You know that TikTok video showing horses running freely on the beach? That’s how I felt when I stopped dancing. About two weeks post-exiting the program, I cut off my hair. To comply with company uniform standards, I’d had to heat train my hair, which left it damaged. I also began getting tattoos and vowed to dress myself every single day. Back then, my top priority was avoiding anything skin-tight. It felt eerily similar to a leotard, and I wanted nothing to do with that.”

Blazer: thrifted. Shorts: Dissh. Poplin shirt: Gap Factory. Loafers: Dole.

“I adore a great blazer — they immediately boost my confidence. The ideal place to find them is a thrift shop. I’ve come across vintage Ralph Lauren blazers for just $5! And be sure to check the men’s section. Men’s blazers are superb because the shoulders are broad; they add flair and look incredibly chic.”

“As a child, I would shop for clothing at Goodwill with my mom. It felt like a treasure chest, and everything was budget-friendly. In middle school, I found patterned blouses with enormous shoulder pads and paired them with my Jordans. My primary thrifting guideline is to never skip an aisle. These days, I like to enter with a playlist that spans at least an hour. Then, I’ll listen to it as I sift through every single garment. It’s quite therapeutic.”

Shirt: Target. Jeans: Madewell, similar.

“When you grasp denim washes, you can pull off denim-on-denim effortlessly. I wore this outfit 50 times this summer. People assume it’s a set, but the jeans are from Madewell, and the top is from an old Target collaboration that I snagged on Poshmark for $10. Still, since both are medium washes, they harmonize beautifully.”

“I’m an instinctual dresser. Before I decide on my clothing, I check in with myself. If I’m not feeling confident, I will choose something that boosts my confidence. Those pieces evolve over time. For a while, I gravitated towards bolder items, like fire-truck red pants. But currently, I prefer neutral shades with relaxed fits. They simply resonate with me.”

Thank you loads, Samantha! You are amazing.

P.S. More individuals share their weekly outfits, including an architecture professor with a pink power suit and an antique dealer showcasing the best button-downs.

(Photos by Kendra Lynece for Cup of Jo.)

Note: If you purchase something through our links, we may earn an affiliate commission or have a sponsored relationship with the brand, at no charge to you. We only endorse products we genuinely appreciate. Thank you very much.