What to Wear on the Bourbon Trail

What is on the bourbon trail? When you’re visiting the bourbon trail, there’s one thing you need to know: dress for comfort. Today, we will discuss What to Wear on the Bourbon Trail and where to go on the bourbon trail.

That doesn’t mean you have to look sloppy—it just means that if you’re going to be clambering around in the woods and climbing up hills, you want something that will let you move without feeling restricted.

The best shoes for bourbon trail hikes are either hiking boots or tennis shoes. Tennis shoes are especially good because they tend not to get as wet when it rains, but both work well. You’ll want to stay away from sandals and flip-flops—they may not be great in mud or water!

Welcome to the world of bourbon, my friends. Whether you’re a connoisseur or just want to get your drink on, you’ve come to the right place.

In this article, I’ll teach you how to dress for success on the bourbon trail. Whether you’re wearing jeans and a t-shirt or heading out for a night on the town in your finest duds, bourbon can be an important part of your outfit—and it should be!

What to wear on the bourbon trail

The Bourbon Trail is a trip through Kentucky, where you can visit distilleries and learn about the history of bourbon. It’s a great way to spend a day or weekend, but what should you wear?

As far as clothing goes, you don’t want to look like a tourist and stick out from the crowd. We’ve put together a guide to help you find out what to wear on the Bourbon Trail so that you can blend in and enjoy your time there.

The Bourbon Trail is a series of distilleries in Kentucky, USA. It’s a popular tourist destination, and if you’re planning to visit any of these distilleries, you’ll want to know what to wear!

Whether you’re going for a day trip or staying overnight at one of the many hotels in the area, there are a few things to keep in mind when packing. These tips can help you make sure that you look great while exploring the area and getting up close with some of the best bourbon in the world.

Packing For Louisville and the Bourbon Trail
Mike and I are going to Louisville, KY with some friends to do the Bourbon Trail this weekend! It’s been a bucket list trip for all four of us and we’re stoked! Packing has taken some real forethought since temperatures average in the 90s and we’re going to be sipping hard booze and eating Hot Browns for four days. Aside from all the eating and bourbon boozing, Louisville is full of fancy places like The Champagnery and the Seelbach Hotel, the setting for the wedding scene in The Great Gatsby. So as you can see, our agenda is a mixed bag of outdoor casual and evening dressy so my suitcase better be, too!

My BFF perfectly described our packing strategy: as each day passes, our outfits should get roomier. (Biggest packing tip of all time: know thyself.) A fitted dress for cocktails and a nice dinner on our first night. A tailored romper and sun hat for bourbon trailing all day Friday (car leaves at 9AM y’all, they don’t play). Then by Saturday all bets are off. I’m not even packing leggings so I won’t be tempted.

What is on the bourbon trail

Here’s a look at the items I’m packing for our four day trip to Louisville, followed by a brief description of each one so you’ll know why it’s worth bringing!

Women’s packing list for summer trip to Louisville, Kentucky, and the Bourbon Trail. Southern-inspired dresses and rompers. Travel essentials for the stylish traveler.Women’s packing list for summer trip to Louisville, Kentucky, and the Bourbon Trail. Southern-inspired dresses and rompers. Travel essentials for the stylish traveler.

  1. White Swimsuit // For the rooftop pool at our hotel. A white swimsuit always looks glam…and best styled with a colorful cocktail or champs. This one is just $25!
  2. Purse Organizer // I always use this in my tote bags; it comes in extra handy for keeping up with travel necessities, room keys, tickets, phones, etc.
  3. Louis Vuitton Neverfull MM // The most aptly named bag of all time. I always travel with my Neverfull because it holds so much and elevates my outfits…even if they cost next to nothing! (With the right bag, nobody can ever tell.)
  4. Tortoise Sunglasses // Glam, oversized, and under $20. Look mysterious while hiding bourbon-induced eye bags, ya feel me?

5, 6. Chanel Foundation and Bronzer // Just re-upped my base makeup with these two Chanel beauty blogger faves. The foundation has SPF 25 and gives you a slight glow. The bronzer is creamy, easy to blend, and gives your skin L-I-F-E baby! You can apply both with this retractable angled brush in a handy travel-friendly size.

  1. Gingham Pleated Dress // A classic southern print updated in this flowy shirred fabric! I bought this dress in pink for Mother’s Day and it’s so comfy and gets all the compliments. Planning to style it with some white Chuck Taylor’s (#12) and this…
  2. Straw Boater Hat // This hat is an homage to my grandfather, born in Bardstown, KY, who loved wearing a straw boater hat with his sharp blazers. A true southern gent! We’re planning to visit the farm where he grew up.
  3. Apple Watch // I’m so attached to this thing for keeping time, tracking steps (we’ll be walking A LOT!), and checking texts without digging my phone out of my giant bag.
  4. Yeti Cooler // We booked a private car for our big day out on the trail. We’re allowed to bring hydration and libations along for the ride so we’re bringing the big daddy cooler to hold it all and keep it cool in the brutal heat.
  5. Floral Midi Dress // Sweet with southern charm, perfect for visiting Louisville’s historic landmarks and neighborhoods. The thick straps make wearing a regular bra easy — no sweating off a sticky bra for me!
  6. Converse Chuck Taylors // The classic white sneaker to wear with cut-off denim and dresses.
  7. Lace-up Sandals // So pretty on the foot, and better yet, so comfortable. The strappy-ness give solids a little more oomph but the barely-there design means they can go with anything.
  8. Rancher Hat // This ivory hat goes with SO much and styles up your casual looks. I can wear it with any of my day time options and disguise sweaty, flat hair in the name of fashion. That’s what you call a WIN.
  9. White Romper // Tailored but not tight, in a crisp summery white. (Almost ordered the pink though!) Breezy, comfy, compatible with a regular bra…it felt like my best chance of staying put together after nine hours on the Bourbon Trail.
  10. Cult Gaia Ark Bag // The bag that works with almost every summery ensemble, dressy or casual. I own the real deal but there are crazy good dupes (HERE and acrylic version HERE).
  11. Open-Back Bow Tie Dress // Couldn’t resist the back detail! Perfect with flat sandals for hitting up the Urban Bourbon Trail around downtown Louisville.
  12. iPhone Camera Stabilizer // This fancy gadget stabilizes your phone while you film video as well as panning and zooming with the touch of a button. A great option if you plan to film a lot of video during your travels.
  13. Sage Green Halter Dress // The vintage vibes and dramatic open back have me swooning over this linen dress. If we choose to do a dressy casual dinner one evening, this is my go-to look for that occasion.
  14. Boho Paisley Dress // Comfy enough for travel, cute enough for daytime sight seeing. Will hide bloat and Hot Brown belly bumps.
  15. Drip Drop Hydration Powder Sticks // What the kids are using to fight hangovers these days. Just add to water like a Crystal Lite packet! The trick is to use before bed and the next day. Will still be packing my bougey coconut water though 🙂
  16. Dolman Sweater // Ahhh the timeless tale of the husband who likes the car’s A/C on -50 while the wife freezes into cryo mode. Planning to wear this comfy, forgiving sweater with cream pull-on shorts on a travel day, or to pick up breakfast from Fall’s City Market in our hotel in the AM.
  17. Nude Heeled Sandals // The shoes that go with everything are the ones that belong in your suitcase. And these are just $23.

Have you ever traveled to Louisville or ventured along the Bourbon Trail? We’re taking some time on our way up there to drive through Bardstown, KY, where my grandfather grew up on his family’s farm. That’s going to mean a lot to me, for sure.

As we’ve researched Louisville we’ve found so many cool things to explore — we are so excited to visit! Where are your summer travels taking you this year?

Ultimate Guide to the Kentucky Bourbon Trail
Enjoy the vanilla or caramel undertones of bourbon when you visit all the distilleries on the Kentucky Bourbon Trail.
What is it?
Created by the Kentucky Distillers’ Association, the Kentucky Bourbon Trail is a trip to a variety of distilleries in Kentucky. You can go with family and friends to try different brands of bourbon, which helps you be part of the community and supports the locals. You’ll also most likely learn the history behind bourbon or the distillery you’re visiting as you talk to distillery experts.

The trail is ideal for those who are 21 years and older, especially if you want to try the whiskey. If you want to buy bourbon from any of the distilleries to take home, feel free; just know that you can only purchase up to 4.5 liters per day.
Is the trail open?
Yes, the trail is open for 2021. You’ll need to check with the individual businesses you plan to visit to see what their hours of operation are.
Where is the Bourbon Trail?
Where it starts

You can start the trail at a place that is convenient for you. The KDA has itineraries you can try if you don’t know where to start.

Distilleries open

Some of the 38 distilleries (all part of the KBA) you can visit on this trail are:
Angel’s Envy
Bardstown Bourbon Co.
Bulleit Frontier Whiskey
Evan Williams Bourbon
Four Roses Bourbon
Green River Distilling Co.
Heaven Hill Distillery
Jim Beam
Lux Row Distillers
Maker’s Mark
Michter’s Distillery
Distillery at Old Forester
Rabbit Hole Distillery
Stitzel-Weller Distillery
Town Branch of Lexington Brewing
Wilderness Trail Distillery
Wild Turkey
Woodford Reserve

Click on the individual links to make an online reservation with each distillery.

Where it ends

Similar to the starting point, the trail ends where you want it to end. Map out a trail that doesn’t take too much time and is the most efficient path.
How long does the trail take?
The trail can be as long or as short as you’d like. The average time it takes for someone to complete the trail is 90 minutes, according to the KDA. You can go on a tour at each distillery, which takes around an hour and a half.
How much does it cost?
The cost will differ depending on how many distilleries you visit. There is an admission fee to visit each distillery.
How do I tour the Bourbon Trail?
Hop in a car and drive to each of the distilleries. If a distillery is within walking distance, you can do that, too!

Can you Uber the trail?

Yes, you can take an Uber to each of the distilleries.
Where should I get a Bourbon Trail passport?
You can get your passport for the trail here. The passport allows you to keep track and get stamps for each of the distilleries you visit.
What should I wear?
Wear comfortable and casual attire when visiting the distilleries.
Can you have a Bourbon Trail bachelor party?
Yes, you can have whatever kind of party or celebration you want when visiting these distilleries (so long as you’re respectful). If you have 10 or more people going on the tour with you, call ahead to make sure the distilleries can accommodate you.
What’s the history behind the trail?
The KBA started the trail in 1999 to celebrate the history and heritage of bourbon. According to the KDA, 95% of the world’s bourbon or “American’s Official Native Spirit” is produced by Kentucky.
Where should I stay?
If you’re looking for a place that gives you easy access to any of the distilleries on the trail, then check out our list of bed and breakfasts that are part of the Bed and Breakfast Association of Kentucky.

What to wear on test day

When you’re preparing for a test, it can be easy to get caught up in the details. Should I bring this or that? Did I memorize enough? Will my answers be good enough?

But there is one thing that’s even more important than all of those things combined. And it’s not a study guide, flash cards, or even your lucky socks. The most important thing for you to bring on test day is your confidence.

When you’re about to take a test, there are some things you might not think about. You might be thinking about how nervous you are, or how much you want to ace the test. But what about what you’re wearing?

It might not seem like a big deal, but what you wear can have an impact on your performance. So we’ve put together some tips for what to wear when it comes time for your next big test!

You should have a light base, a t-shirt or an oxford/blouse, and at least a light sweater or jacket ready to wear, if not a jacket jacket. Layers means no shorts/ no short skirts.

What to wear on test day (seriously)


By Alex S

Advice for test day is easily doled out, and often hard to actually follow.

Don’t cram the night before. Sleep as much as you possibly can. Eat a real, but not heavy breakfast, with only as much caffeine as you normally have. These are your goals, at least.

On the question of clothes, the advice you are most likely to get is to be “comfortable.” In blogs and forums, I have seen shorts widely recommended for warm days, sweats for cold ones. These kinds of suggestions employ a rather narrow definition of “comfort,” which does not have to mean “slacker attire,” just as “comfort food” does not have to mean “Cup Noodles.”

You actually do need layers. There is about a 50% chance the room will be freezing, especially if the test is in a warmer month. You should have a light base, a t-shirt or an oxford/blouse, and at least a light sweater or jacket ready to wear, if not a jacket jacket. Layers means no shorts/ no short skirts. You can’t layer coverage on your legs. It is safe to assume the room will not be so scorching that wearing pants will prove distractingly difficult, but if you take your seat at a cold desk in a cold room with only shorts and a t-shirt, your focus will be compromised before you start filling in your name.

The test is not a dinner party; there is no reason you cannot take it in a coat. If the room is frigid, not only will you be as warm as you need to be, you’ll be more comfortable than your peers who either didn’t come prepared or have some stigma about wearing outerwear indoors. Comfort can be competitive. If you feel like nothing can touch you when you’re in your down jacket or giant hoodie, that’s a feeling you can harness for the exam.

This is the point where my advice bifurcates a bit. Wear sweats or temperature regulating gear ONLY if that’s part of your normal look. Comfort on test day is the same as comfort during a normal school day or workday. In other words, if it would normally feel weird for you to dress like you plan on a day of Netflix, or like you are about to hike the Appalachian Trail, then don’t do that! Comfort means feeling confident, which means wearing your “best” clothes more than the most ergonomic ones. If it helps you get in the zone, dress up a bit, generally going for “business casual.”

For my own part, I like to wear a proper oxford shirt even when working at home. Real confidence comes from taking yourself seriously, and feeling put together can help establish a capable mindset. There is no single strategy for every test-taker. Be comfortable, yes, but remember that the test site is a competitive, formalized space. Picture someone you would assume did well and embody that!

Where to go on the bourbon trail

There are many great places to visit on the bourbon trail, but here are some of our favorites.

The first stop on most people’s bourbon tours is the Buffalo Trace Distillery in Frankfort, Kentucky. This distillery is located just off I-64 and offers daily tours for a nominal fee. It also has a gift shop that sells all manner of bourbon-themed merchandise including t-shirts, hats, glassware and other souvenirs.

Another popular stop on the Bourbon Trail is Four Roses Distillery in Lawrenceburg, Kentucky. This distillery offers free tours and distills its own bourbon at its facility on site. They also have a tasting room where you can sample their products before purchase as well as a gift shop full of unique items like chocolate-covered cherries or gourmet chocolate chip cookies with Four Roses whiskey in them!

If you’re looking for something different from your normal bourbon tour experience then make sure to check out Woodford Reserve Distillery in Versailles, Kentucky! This distillery offers tours but they put their own twist on it by offering horse drawn carriage rides through their property before or after your tour ends so you get some fresh air while learning about whiskey production!

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