Bleisure Much? Packing for a Business Trip and Beyond

Jessie Beck

Bleisure travel (no, that’s not a typo): whether you’ve heard of this strange sneeze of a word before or not, there’s a good chance — especially if you’re a millennial — that your last business trip was actually a bleisure trip. Increasingly, business travelers are taking advantage of the opportunity to extend work trips for leisure; arriving the weekend before a conference to sightsee in a city, or taking a couple of PTO days after a trip to explore, visit friends, or decompress after a busy week.

I, too, am guilty of participating in the bleisure trend. I’ve flown directly from a conference in Boston to a weekend at my parents in D.C.; scheduled in a 4-day pit stop in Taipei after a sight visit in Sri Lanka; and arrived the weekend before MozCon in Seattle to bike the annual Seattle to Portland ride.

Logistically, these combined business and leisure trips are more complicated. From separating expenses to making sure your work travel policy allows for bleisure, there’s more to consider than usual in the planning phase. And of course, there’s my favorite question: how do you pack for this trip? How do you go about packing for a business trip you’re extending into a vacation? As always, we’ve got you covered (literally):

Tips for Packing Light on a Business Trip

With your schedule tightly packed and no time to waste, packing light is just as important on a business trip as it is on any other — even if you can expense that checked baggage fee. When packing carry on only for a business trip, we use the same tested and true packing tips that have helped us for other adventures such as:

  • Get a good carry on sized bag: you’ll restrict yourself from overpacking; a travel backpack is best for freedom of movement and flexibility. 
  • Ship business/conference supplies: shipping supplies won’t just lighten your bag, it’ll also help you save time at the luggage carousel and avoid any lost luggage issues.
  • Pack a couple of days in advance: to avoid frantically stuffing everything and anything in your bag.
  • Limit “just in case” items: medications, business cards, and IDs aside, you’ll be able to pick up most anything else you forget or unexpectedly need on the road.
  • Take advantage of hotel freebies: like shampoo and blow dryers, and leave these items off your packing list.
  • Use packing cubes to stay organized: and waste less time packing and unpacking.
  • Roll clothes: while it won’t save you more room, it’ll help you organize your bag and keep clothes from wrinkling.

Pro tip: need a place to stash your luggage for the day? Download LuggageHero or KnockKnock. Both apps help you find places to securely stash luggage for a few hours (though in limited locations).

Leisure and Business Travel Packing List Template

When it comes to building a travel wardrobe that can take you from conference hall to weekend in the mountains, it’s all about choosing versatile, wrinkle-free items. Even though you’re rolling two trips into one, it’s less about packing more and more about packing the right items. After all, the right pair of shoes, accessories, and a blazer (or lack of one) can transform an outfit entirely.

Before we leap into clothing recommendations and outfit ideas, here’s a rough packing list template you can follow using items from your own closet, our recommendations below, or both:


Approach your list like a capsule wardrobe and choose 10 staple items. This is enough for 5-10 day trip:

  • 4 tops
  • 3 bottoms
  • 2 jackets
  • 1 dress
  • + underwear (obviously)


Dress outfits up or down with a couple small, easy to pack accessories.

  • 2-3 pairs of shoes
  • 2-3 pieces of jewelry
  • 1 purse
  • Sunglasses
  • Bandana or scarf (depending on season)
  • Hat (optional)


Stick to travel size only and rely on hotel freebies (i.e. blow dryer) when possible.

  • Toothbrush + toothpaste
  • Basic makeup kit (3-4 essential items)
  • Razor
  • Lotion
  • Basic first aid kit
  • Tweezers + nail clippers


It’s a work trip after all, and you’ll probably be taking part of your office. Take it all in a bag specifically designed to carry your mobile office, like the Laptop Backpack. It’s a versatile secondary bag with considered details for air travelers. Slide it under the seat of most airplanes and carry all your electronics, chargers, a change of clothes, and your in-flight essentials.

It’s the perfect companion to a duffle bag or rolling suitcase and acts as your personal item on the plane.

In that personal item pack:

Miscelaneous Stuff

For items that defy categorization:

Clothing for Women’s Business Travel Wardrobe — and Beyond

Since it’s not just about how much you pack, but what you pack, here are a few specific clothing items I love for combination business and leisure trips — loosely based off the packing list I used for a summer conference and birthday trip to Seattle.

3 Bottoms: Trousers, Leggings, and Jeans

Leggings (ADAY, $135)

These leggings by ADAY, a technical clothing company for women, have recently replaced my Lululemon leggings as my favorite travel pants. They’re comfortable, versatile, almost impossible to wrinkle, and breathable in warm weather.

Tip: if you’re between two sizes like me, opt for the smaller one.

Work Pants (ADAY, $125) 

Traditional business clothes suck for travel because they’re hard to style as anything but and easily wrinkle. That’s not the case with the Turn it Up Pants by ADAY which, like the leggings, are comfortable, don’t wrinkle, and are actually stylish enough to work into a more casual outfit.

For the full head to toe, check out their uniforms, like The Monday.

Jeans (Sezane, $125)

We all have our favorite pair of jeans and though I’ve been wearing BDG for years, I’ve recently fallen in love with the denim line from French brand, Sezane. No matter what denim brand you call your favorite, though, pack those.

This is cheating a bit — but I’ll sometimes throw in a pair of lightweight jogging shorts (or bike shorts) for workouts. Fortunately, ADAY’s leggings work well for hikes and yoga when I don’t.

1 Dress: The Little Black Dress

Leith Racerback (Nordstrom $49)

Who doesn’t love a great little black dress: so easy to style, so difficult to stain. It’s a travel list essential.

For a business to leisure trip, choose a simple yet conservative dress like the Leith Racerback (Nordstrom $49).

The simple shift cut means it works just as well layered under a blazer for a meeting as it does over a bright t-shirt for a casual day out.

4 Tops: T-shirt, Sweater, and Blouses

For tops, I want basic pieces that’ll be easy to layer, style up or down, and options for both cold and warm temperatures. For this trip, I went for:

Basic t-shirt ($25 Everlane) 

If you haven’t heard of Everlane yet, then there’s no better time than now. Their clothes are timeless, affordable, and quality — all things I want in my travel items. Bring a basic t-shirt in a neutral color to layer under a blazer or wear on its own with jeans. Or, go bright and have it be your pop of personality.

Sweater ($50 The LOFT

A fitted sweater is always a nice business casual piece.

Layer it over a collared blouse for a more professional look, or throw it in your day bag in case that jean-and-t-shirt outfit isn’t keeping you warm enough while exploring around town.

Collarless blouse ($40 Madewell) 

For your first blouse, either go tank or long-sleeve, depending on the season. For a summer trip, a simple blouse like Madwell’s ruffle-sleeve tank works well. It’s basic but fun, and unlike a lot of business clothes, machine washable (win!).

Collared blouse ($69 Azalea) 

For the second one, pack a collared top like Azalea’s t-shirt blouse.

This gives you a professional look underneath your fitted sweater or blazer, or a casual yet stylish outfit when styled with a pair of jeans or leggings.

2 Jackets: Blazer and Bomber

Ministry of Supply ($245)

Ah, the blazer: a staple of every business trip. How do you find one that’s just as easy to pack as it is to wear? Business Insider suggests Ministry of Supply , which is stretchy, comfy, and wrinkle-resistant, while being structured enough to hold its shape. My friend and business traveler, loves Everlane’s ($125) classic blazer. I have a cotton-blend blazer from Target that I wear, or go the cardigan route for business casual events.

Above the Clouds Jacket ($128)

For the leisure side of travel, I want a jacket that lies somewhere between streetwear and activewear.

This way, it’s cute enough for urban sightseeing, but also has the technical specs I need for a quick day hike or sudden rainshower.

Fortunately, the rising athleisure trend makes this easy: an athletic bomber like Lululemon’s Above the Clouds Jacket ($128) fits the bill.

2-3 Shoes: Flats/Heels and Sneakers

Shoes can transform an outfit — but they can also take up a lot of room and weight in your bag. Try to stick to two pairs, ideally a professional pair (be it flats, booties, or loafers) and a casual pair (like sandals or sneakers). If you need to wear heels, throw them in as your third and final pair.

Professional Pair of Shoes (Rothy’s $145+) 

For flats, I’ve heard great things from friends about Rothy’s loafer and pointed-toe flat.

They’re “just as comfortable as a sneaker” and made from recycled material (how many flats can say that?).

TOMS, always a favorite brand of the Tortuganaut squad, also makes some really comfortable flats ($89) and, for cold weather, booties ($110+).

Casual Shoe (sneakers or sandals) 

Depending on your style, either go for a fashion sneaker you can also wear outdoors, like Reebok Classics ($55) or Keds ($40+). For a more summery look, bring a pair of comfortable yet nice-looking sandals like anything by the stylish vagabonds at Soludos ($60+). Birkenstock sandals ($100) are also a comfortable and back-in-style option.


Finally, your accessories: those items on your packing list that are small enough to fit in your pocket, but powerful enough to transform your look. Here’s a sample of what’s in my accessory bag on a bleisure trip:

Jewelry (Amano studio, cost varies)

A long necklace helps dress up work outfits, while a pair of large statement earrings, like those from Amano Studio’s Brass Gypsy Hoops ($38 — appropriate name, right?) are a fun addition to any outfit for nights out. 

Bandana or scarf (UO, $8 / Zara, $25) 

Add a little flair to an everyday outfit with a cute bandana, or stay warm wherever you are with a cozy blanket scarf.

Purse (Baggu, $32)

I bring my Baggu duck bag everywhere — including bleisure trips. It folds down well and fits my laptop perfectly.

For something fancier, Baggu also has some nice (though expensive) leather bags.


If you don’t already have a favorite pair, check out our full list of the best sunglasses for travel. Honestly, I’ve just been wearing the same pair of cheap $20 vintage store glasses for years.

Work Outfit Ideas

Alright, now that you’ve thought through your list and have your 10 items. Here are a few ideas on ways to style them for the business side of your bleisure trip:

  • Leggings + collarless blouse + necklace + blazer + flats
  • Trousers + collared blouse + sweater + flats
  • Dress + blazer + heels
  • Trousers + basic t-shirt + sweater + heels
  • Legging pants + dress + blazer + flats
  • Trousers + collarless blouse + blazer + heels

Leisure Outfit Ideas

With those same 10 items, here are a few more casual combinations.

  • Dress + bomber jacket + sneakers
  • Jeans + t-shirt + bandana + bomber jacket + sneakers
  • Trousers + t-shirt + sneakers
  • Leggings + t-shirt + bomber jacket + flats
  • Leggings + sweater + flats
  • Jeans + collared blouse + flats

While researching this post, I came across a lot of great options. If none of these suit your style, explore more on this Bleisure Travel Pinterest board.

Packing for an Extended Business Trip: Men’s Picks

Shawn Forno joined Jessie to contribute the men’s picks for this piece. Thanks Shawn.

Jean, Chinos, and Stylish Travel Pants

Travel pants have gotten so good (and good-looking), that I typically pack the same pants for any trip—whether it’s work or a vacation. If you one of the poor unfortunate souls that has to wear a suit, this is how to pack it. Here are a few solid slacks that work for casual business drinks or exploring the city in between pitch meetings:

Bluffworks Tailor Fit Chinos ($135)

These awesome travel-friendly pants are my go-to slacks for a long business trip or a casual beach vacation. They’re stain-resistant, water-resistant, comfy as heck, and feature zippered interior pockets so your wallet/phone/keys don’t fall out while you’re passed out on the redeye flight from JFK.

I can’t say enough about these pants. They look good everywhere and feel great doing anything.

Pro tip: get the Harvest Gold color if you want that extra stylish pop


Uniqlo Relaxed Ankle Length Pants ($39)

I’ve been consistently impressed with Uniqlo’s travel gear, and their pants are no exception.

Budget friendly, modern, and stylish as all heck, Uniqlo’s ankle length pants are great for mixers and working on the road, but still look comfy enough for a night out on the town.

If pleats don’t do it for you, snag a pair of the Ultralight Kando Pants ($39) or the Stretch Fit Skinny Jeans ($39) in any color you want.


Outlier Slim Dungarees ($198)

The “workcloth” fabric on these travel jeans gives an exquisitely designed pair of pants a more comfortable feel than traditional denim with a more sophisticated look than your average travel pants.

They’re stretchy enough to rock climb in (I have), and are designed to impress at any business function. 10 out of 10. If you can afford to splurge on a great pair of business friendly travel pants, go with Outlier.

Hybrid Shorts

I always pack a bathing suit when I travel. Always. Seriously, it doesn’t matter if I’m going to the moon—I bring something to swim in. Business trips have hotels, and hotels have hot tubs. It’s great to pack a pair of quick dry hybrid shorts you can swim in or hike in if you have some time to kill on the end of a business trip.

RVCA Weekend Stretch Shorts ($50)

As a former surf instructor, I know that RVCA makes a solid product that can handle the elements (they’re known for surf gear). These shorts are built for the water, but still perform on land.

The weekend shorts have belt loops—which are a big plus compared with a draw string or elastic waistband. Dress these up with a belt if you need to. Polycotton blend fabric means they’ll dry quickly, and they have the ever-important 2% elastane (that’s actually a lot) for a ton of stretch for hiking, biking, climbing, or even cliff diving. Get a bright color. You deserve it.

Manduka Now Yoga Shorts ($60)

When it comes to staying in shape on the road, guys are pretty lucky. You can wear a t-shirt (or the Airism tank top) and a pair of basketball shorts and you’re good to go. If you want to upgrade your workout style try these.

They feature a surprisingly stylish cut (even the pockets are swag-tastic) with enough stretch and give to hit any yoga pose—which is more than you can say.

Uniqlo Airism Tank Top ($9) 

I can’t say enough about these cloud-like tank tops. They weight almost nothing. It’s unreal. The mesh material breathes like a dream, never stays wet, and somehow sheds odor like a boss.

I have two and they come on every trip—business or pleasure. The best part is that they’re so light you won’t even notice you packed them.



H&M Slim Fit Crew Neck T-shirt ($7)

These oddly comfortable t-shirts are the basic piece that’s missing from your wardrobe. Grab a few plain white t-shirts to wear under your oxford button down and supplement your normcore style game with a couple of flashy primary colors. The 10% rayon blend means they won’t wrinkle easily.

This is the perfect basic travel t-shirt and is affordable to boot.

Uniqlo Airism Shirt Collar Polo Shirt ($19)

If you’re not a fan of polo shirts, this lightweight, sweat wicking shirt will change your mind. If you are a polo shirt guy—look no further my friend. You’re home. The stiff (in a good way) collar, sharp silhouette, and tailored look make this shirt a welcome addition to any business trip or happy hour. Seriously, I wore this shirt at an all night swing dance in NYC the other week, and it handled that packed, sweaty room of hipsters like a pro. Plus, I got some style compliments (which is tough to do with the vintage crowd). Plus it’s only $20. That’s nuts.

Uniqlo Knitted Short-sleeve Polo Shirt ($19)

I know I’m kind of Uniqlo fan-boying, but they make incredible performance gear at an affordable price.

If you are into that vintage look, pick up the knitted polo shirt. Part sweater, part time machine, the tailored waist line will make you look like Sinatra.

And it’s still machine washable. So that’s awesome.

Travel-Friendly Blazer

Unless you’re packing a suit, you’re going to need a blazer. So why not bring one that’s literally designed for business travel?  

Bluffworks Gramercy Slim Travel Blazer ($295)

Built for comfort on the plane and packed with all the pockets, keep your phone, ticket, passport, book, and kitchen sink all safe an organized on your next long haul flight. Lightweight and breathable for hotter climes, it won’t weigh down your bag if you pack it away once the deal is done. Make sure you get your measurements just right before you splurge for a travel blazer, though, because fit is absolutely everything.

Read this complete guide to travel blazers for sizing tips and a few more great options for any budget.


Carry on travelers—even business travelers—can’t afford to bring too many pairs of shoes. So invest in one pair of comfy, durable, lightweight travel shoes that can handle any environment and bring another fancy pair for that meeting. Or don’t. One pair of shoes is more than enough.

People Footwear Stanley Shoes ($60) 

These ultralight foam shoes put clunky Toms to shame. Built to handle any activity, these shoes are about as light as they come. Made from 3D-printed breathable mesh, it’s like walking on a stylish cloud. Pack a pair in your backpack and forget about ’em. I like the red ones.


Finally, your accessories: those items on your packing list that are small enough to fit in your pocket, but powerful enough to transform your look. Here’s a sample of what’s in my accessory bag on a bleisure trip:

BUFF Lightweight merino scarf ($30) 

A BUFF scarf does it all. It can be a sleep mask on a long flight, a washcloth in an airport bathroom, a hat for chilly bus rides, or *gasp* even a stylish scarf. I use mine all the time.

Ministry of Culture Wax Lined Hip Pouch($35)

Embrace your inner hipster and kiss your business meetings goodbye with these durable, stylish, and super useful hip pouches. I’ve had one for three years now, and it’s now become a travel staple. 


If you’re extending your next business trip for some non-work-related travel fun, there’s absolutely no reason why you can’t still pack light and only bring a carry on travel backpack. Instead of packing more things, pack the right things.

  • Use the same packing light tips you would for any other trip
  • For clothes, stick to 10 items (4 tops, 3 bottoms, 2 jackets, 1 dress), 2-3 pairs of shoes, and accessories to transform your look
  • Whenever possible, pack versatile, comfortable, and wrinkle-free items

Now, go make the most of your next work trip!


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