How Bailey Sees It
Welcome to What Bailey’s Wearing
If you know me, you know I’ve always believed that what we wear tells a story. It’s more than just clothes — it’s confidence, creativity, and a little glimpse into how I’m feeling that day. This space is where I share my real-life outfits, favorite finds, and go-to looks for everything from coffee runs to nights out.
Expect a mix of everyday style, affordable pieces, and a few statement moments that just feel so Bailey. Whether it’s a classic denim day or a “let’s be extra” kind of night, this column is all about finding joy and personality in what you wear.
So grab your iced coffee, scroll through, and maybe find a little outfit inspiration along the way, because life’s too short to not wear what makes you feel good. 💕
Ella Langley Concert
Okay, let’s talk about this dress — the Linny Mini Dress by LoveShackFancy. I wore a size medium and honestly, it’s one of the most comfortable and flattering dresses I’ve ever put on. The top has built-in support and hidden boning (a total game changer), so it holds its shape beautifully without needing a bra. Plus… it has pockets. Need I say more?
I rented it through my Nuuly order, but now I’m seriously considering buying it for future events because it’s that good. It’s originally $375 on the LoveShackFancy website, and while that’s definitely a splurge, I’d say it’s worth every penny for how confident and cute it made me feel.
Rating: 10/10.
Now, the red cowboy boots — super cute, but they were a different story. I ordered them from Shein, and while they photographed perfectly, they were definitely more for looks than comfort. By the end of the night (and the walk home), they had to come off.
Rating: 5/10.
Boos Before I Dos
This ZESICA Women’s Summer Boho Strapless Maxi Dress from Amazon was such a pleasant surprise! I wore a size medium, and it fit perfectly—snug enough at the top with the smocked bodice to stay in place, but flowy and comfortable through the skirt. The length hit right above my ankles, which I loved, and it moved beautifully when I walked.
I wore it to an engagement and wedding party on November 1st, and it was just right for the breezy fall night, light but not too summery. For only $50.99, this dress feels like such a steal. The off-shoulder, tiered design gives it that effortless boho vibe that works for so many occasions.
Overall rating: 9/10. Comfy, flattering, and perfect for dressing up or down. Definitely one I’ll be keeping in my closet rotation.
Kaitlyn's Brunch
This Firerie Women’s Elegant Romantic Holiday Pleated Maxi Dress from Shein definitely made a statement. I wore a size large, and the ombre floral print photographed beautifully. It gave total boho summer vibes and was perfect for pictures. The material itself felt nice and well-made, which I wasn’t expecting for the price. When I first bought it, it was $28.79, but it’s now on sale for $18.47 on Shein’s website, such a steal for how flattering
That said, this is one of those dresses that’s prettier to look at than to move in. The skirt tapers down in a mermaid-style fit, which looks flattering but doesn’t leave much room to walk comfortably. It was also a bit see-through, so I’d say it’s best for styled photos or a quick event rather than a long night out.
Overall rating: 7/10. Gorgeous in photos and made of good material, but not the most practical for real-life wear.
Kaitlyn's Bachelorette Dinner
This Women’s Summer Halter Neck Dress from Shein was such a fun and easy outfit. I’m wearing a medium, and it fit really comfortably. The halter neck tie made it super adjustable, which I loved, and it made me fall in love with this top style even more. It paired perfectly with my Dolce Vitas, giving it that effortless summer look that still felt put together.
When I first bought it, it was $36.98, but it’s now on sale for $20.38 on Shein’s website, such a steal for how flattering and comfy it is. The only thing I wish is that there had been a bit more fabric at the top, but overall it wasn’t tight or constricting at all.
Overall rating: 8/10. Super cute, comfortable, and easy to style for just about any summer outing.
Graduation Pictures
This Graceful Breeze Peplum Poplin Mini Dress from Expectations Too was the perfect choice for my graduation pictures. I wore a size large, and it fit just right. It wasn’t too long or too short, just the perfect length to feel classy while still showing a little style. The adjustable bow around the waist was one of my favorite details because it added such a flattering touch.
The top was slightly sheer, which made finding the right bra a little tricky since it could show through. I also wasn’t the biggest fan of the button under the armpit area on the sleeve, but it wasn’t a dealbreaker. For the price of $62, this dress was both cute and affordable, and I loved how it photographed.
Overall rating: 8/10. A beautiful, feminine option for graduation photos or any spring event.
Graduation Ceremony
This “Olivia” Eyelet Midi Dress from I Just Have To Have It in Starkville, Mississippi, was the dreamiest pick for my graduation ceremony. It retails for $88, and I can honestly say it was worth every penny. I wore it all day and night, and it was so comfortable the entire time.
The pink color was absolutely radiant and made me feel like a princess. I loved the cutout detailing, especially toward the bottom, which kept it light and breezy, perfect for a warm Mississippi day in May. The fit was flattering, feminine, and easy to move in, making it one of my favorite dresses I’ve ever worn.
Overall rating: 10/10. Comfortable, elegant, and full of charm, this was the perfect dress to celebrate such a special day.
More Casual Looks!
Let’s be real, I don’t wake up in heels and a full face of makeup every day. This section is all about the outfits I actually wear on a daily basis. Whether I’m running errands, grabbing coffee, heading to work, or just hanging out, these are my go-to comfy but cute looks that still make me feel put together. Because even the casual days deserve a little bit of style.
Lululemon Class Fit
This outfit was such a comfy and practical pick for a busy day. I wore it while running errands and it would be just as perfect for going to class or grabbing coffee on the go.
I paired the Lululemon Define Jacket in black (size 8), which retails for $128, with the Ebb to Street Tank Top in light support, B/C cup (size 10), retailing for $68. The Align High-Rise Pants 25" (size 8) are a total staple piece and retail for around $98. For shoes, I went with my Hoka One Bondi 8s (size 10), which retail for $165, and they kept me comfortable all day.
Everything about this look was effortless, flattering, and so easy to move around in. The Define Jacket gives that sleek, fitted look, the Aligns are buttery soft as always, and the Hokas tie it all together with the perfect mix of comfort and support.
Overall rating: 10/10. A go-to outfit for staying comfortable while still looking put together.
Lululemon Running Errands
This look was my go-to for heading to the gym or running to class. I loved how low-effort it was while still making me look completely put together. Everything felt super comfortable but still cute enough to wear all day.
I wore the Lululemon Swiftly Tech Short-Sleeve Shirt 2.0 (size 8), which retails for $68, with the Lululemon Align No Line High-Rise Pant 28" (size 8), retailing for $108. For shoes, I had on my Hoka One Bondi 8s (size 10), which retail for $165, and they’re always a must for comfort and support.
The Swiftly Tech top kept me cool, the Aligns were buttery soft as always, and the Hokas made the outfit perfect for walking around campus or hitting a quick workout.
Overall rating: 10/10. Easy, effortless, and the perfect mix of comfy and cute.
Perfect Shopping Out and About Fit
This outfit became one of my go-tos for class because it was comfy, easy, and still cute enough to wear around town. I’m wearing the Offline by Aerie Real Me Flirty Shorts (size medium), which retail for about $59.95 on the website. They’re soft, breathable, and perfect for those days when you want to be comfortable but still look like you tried.
For the top, I paired them with my Mississippi State Baseball pullover from B Unlimited (size large/x-large). It retailed for around $50, and sadly, I don’t think they make these anymore. It’s one of those perfect pullovers that gives just the right amount of warmth for a chilly morning or a casual day out shopping.
Overall rating: 8/10. Super comfortable, easy to throw on, and perfect for those laid-back class days.
Dinner With Friends
This look was simple, comfy, and perfect for a laid-back day. I wore the Lululemon Scuba Oversized Half-Zip Hoodie (size medium/large), which is one of my favorite cozy pieces, with a Gold Hinge skirt (size large) that retailed for around $58. For shoes, I had on my Vintage Havana DREAM White/Pink high-top sneakers (size 10), which originally retailed for $190 but are now on sale for $59.
The outfit gave total “off-duty” vibes and was great for running errands or hanging out, but it wasn’t anything super special. Still, everything was comfortable and easy to wear, which is always a win in my book.
Overall rating: 6/10. Cute and casual for a chill day, but definitely more of a cozy comfort look than a statement outfit.
