Get Ready With Me Winter Edition: Men's Classic Prep Style With a Twist

As an August baby raised in the Deep South, I’ve never looked forward to the arrival of winter. I feel most at home in five-inch chinos, a linen shirt, and Birkenstocks. Unfortunately, since I can’t afford a condo in Miami, I’m stuck adapting to the changing seasons and the demands of Mother Nature.

Still, there is one shining light that almost makes winter bearable: fashion. Coats, scarves, hats, gloves, jewelry, socks, ties, bags, and shoes transform a cold, boring season into a daily fashion show filled with excitement. What will I wear today, and how will I show up in the world? That single question is what pulls me from bed each morning, compelling me to face the day and participate in society—however begrudgingly—until spring finally returns.

I knew that getting through this cold day would require color—lots of color. So I started with a bright yellow silk tie featuring a horse motif by Thomas Pink. Upon closer inspection, I noticed that while all of the horses are positioned facing east, there is a single horse facing west, calmly eating a carrot. But what does it mean?

The goal for the day was to be preppy, comfortable, and warm, while wearing layers that could be removed as needed, since I planned to work from a coffee shop for most of the morning. I didn’t want to look as though I had tried too hard to lean into an equestrian theme, so I scrapped the Thomas Pink tie and narrowed my selection down to two bow ties.

The striped bow tie was purchased in 2020 as part of a lot of approximately fifty ties from an eBay seller who was clearing out her late husband’s wardrobe after he passed away from COVID-19 complications. I almost wished she hadn’t shared the details surrounding the sale, but then I reminded myself that the earth is essentially a giant graveyard—we’re all living in recycled space and constantly breathing recycled air. What harm is there in using objects previously owned by someone who has passed on?

As an avid thrifter and vintage lover, I’m almost certain that many of my belongings were once cherished by people who are no longer among the living. In a way, keeping these items in circulation feels like a quiet act of remembrance, a way of honoring lives that came before us. If the wife had no use for the ties, why not pass them along to someone who will wear and enjoy them, rather than letting them sit unused and fade away? I'm happy to admit that I'm really enjoying the bow ties.

Choosing shoes was perhaps the easiest part of the entire process. A few months ago, I gave away all of my dress shoes in an ambitious attempt to rebuild my collection from scratch. The G.H. Bass Weejun is so easy to wear that it has become my go-to shoe for an effortless, casual prep look. They run a half size large and are hell to break in, but once you get past those hurdles, you’re good to go. The wine color adds just the right amount of sauce, and the Lincoln bit makes them anything but your grandfather’s penny loafer.

Yes, I know straw hats are intended for warm-weather use, but that’s the thing—it wasn’t exactly cold. It was cool, sunny, and a bit strange. I can’t quite explain it; you’d have to be in Atlanta to understand. I didn’t feel uncomfortable wearing a straw hat because I knew the temperature would increase significantly as the day progressed.

In other news, I’m long overdue for new hats, and I have my eye on several from Bailey. Updates to come.

Bags will always be my first love, so let’s get into it. This vintage L.L. Bean messenger fits a 13-inch MacBook along with all of my coffee-run essentials, while delivering the classic American charm I crave. I appreciate a well-worn leather bag—one that hasn’t been abused, but loved. The shoulder strap is actually a repurposed Ralph Lauren belt that just so happened to serve double duty beautifully.

Its companion is a vintage Coach Bleecker business tote in turquoise—a color I wouldn’t normally choose. But when I saw it, that little voice in my head told me we could make it work… and here we are. No regrets. Can we agree that Coach does leather exceptionally well, creating durable, high-quality goods that are built to last without breaking the bank?

Coach’s turquoise instantly puts me in the mood to pack up my things and head to the nearest beach, grab seafood tacos and margaritas, and leave my troubles behind. What more could I ask for in a bag? I typically choose bag colors based on my preference for classic, warm, earthy tones, but this one was selected purely for the mood it evokes. I may not be at the beach just yet, but every time I glance at this turquoise tote, I’m reminded that I will be soon—it’s only a matter of time. 

Bracelets have been an integral part of my life for the past fifteen years, so choosing which one to wear isn’t as simple as it may seem. I usually select my jewelry once I’m fully dressed and just about to walk out the door. I like to sense the energy of the day before choosing these final touches.

My bracelet for the day isn’t chosen simply to match colors, but rather for the overall balance it brings to the ensemble. I nearly opted for a bright white howlite bracelet to introduce a crisp note of freshness before ultimately settling on our new malachite piece.  I’m wearing three green pieces, each in a different shade, creating subtle contrast. 

The trench coat has long been a staple in my wardrobe but I haven't had one this color in many years. They weren't warm enough for New York winters and they were too warm for any other season. It feels great to be able to wear trench coats again just to get coffee or run errands. A good trench instantly gives the impression of effort even when little was made. 

This vintage find by Austin Reed features a removable lining, making it just warm enough for our current weather conditions. I’m almost embarrassed to admit that I was well into my thirties before realizing it wasn’t necessary to spend over $1,000 on a Burberry trench when high-quality alternatives exist—especially if, like me, you have an appreciation for vintage.

After scrapping the Thomas Pink horse-motif tie, this linen bow tie—one I’ve had for over a decade and worn sparingly—was begging to go outside. I happily obliged, heating up the iron for a quick refresh, and we were ready to go.

In my opinion, linen is the ultimate casual-luxury men’s fabric because it’s both durable and delicate at the same time. If you’re wearing wrinkled linen later in the day, people understand. Rather than assuming carelessness, they assume you’re booked and busy.

Linen may look significantly less formal than silk or wool, but a bow tie is still a bow tie—especially in a world where most men don’t even own one. But that’s a topic for another day.

Thank you for reading.

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