So I’ve been using the same small set of clothes for many conferences now, with a little variation from one to the next.
It packs light, works across all kinds of weather, and most importantly keeps me looking sharp without any effort on my part.
I have been able to really go to probably four conferences in the last four to five months and look sharp, and in fact, always get compliments besides being able to travel pretty darn light.
How is this doable?
Check out the video right here for an inside peek into my interchangeable wardrobe! — below, I’ll outline some of what I talk about in greater detail.
Okay, let’s get right into this.
1. Understand your needs
By doing this, you can pack appropriately.
First, look at the weather.
Are you going to be indoors most of the time?
Are you gong to give a presentation?
By answering these questions, you will know what to bring with you in general. Knowing what you’ll need means thinking about where you’re going and what you’re doing.
For example, most of my trips involve hotels and convention centers — I need to take the weather outside into a little bit of consideration, but mostly I’m dressing for climate-controlled indoors settings.
That means long trousers, dress shirts, and jackets for the most part.
If I’m going somewhere really formal I’ll throw a suit into the mix, but there’s really not that many suit-and-tie occasions on my agenda these days.
I pack a little bit of variety so my outfit can adapt to different places.
I’ve got my dress trousers and nice leather shoes for a more refined look, and when I want to dress it down a bit I use dark denim jeans and a pair of Western boots to relax the look.
What I don’t have is a lot of “just in case” items.
I leave the heavy overcoat at home and skip the suit unless I know there’s an occasion that will demand it.
They’re not going to be useful 95% of the time, so there’s no reason to worry about them.
2. Protect your investment
Good jackets and shirts are not cheap.
My travel wardrobe alone is worth about 5-8K depending on what I pack.
You don’t want to arrive at your destination and all of a sudden realize your shaving cream shot off all over the place and ruined some of your clothing.
Anything that can spill or stain (toiletries, mostly) goes in my Dopp kit.
A Dopp Kit is a small, zippered container that I put inside my other luggage.
It has a lined inside, so that even if my shampoo explodes at 15,000 feet or something like that, nothing but my other toiletries get messed up.
Next is something a lot of guys skip on – the garment bag.
I use one whenever I travel to Austin, Texas in my car. I don’t recommend the garment bags that you get for free.
Now, I don’t think it’s going to be stopping bullets here, but I can tell you it stops all types of stains, water, etc.
I can throw this around and not fear that I’m going to be tearing up my clothing and it keeps my clothing reasonably wrinkle-free.
And by ‘wrinkle-free’, I mean I haven’t had to press or iron my jackets for probably two months and I’ve taken them all over the place. They get a few wrinkles, but those usually fall right out.
Again, I love how it folds up on itself. It’s a great way to be able to take the clothing and protect it, so number two, protect your investment.
3. The Interchangeable Wardrobe
Whenever I’m traveling and if I’m traveling light by plane, I usually pack a little bit lighter. Maybe I’ll only take two jackets with me, one I’ll wear, but on these last few trips, I took three. I would usually be wearing a jacket, not necessarily in the vehicle – I’d hang it up.
Now, here is where we really come to the secret of packing light.
I’m able to get by with so few garments because almost all of them can be worn interchangeably.
I don’t have one jacket with a couple shirts that go with it, and then another jacket with two different shirts to match that one.
I can wear any of my jackets with any of my shirts, and vice versa.
I always travel with at least two jackets, and preferably three (it’s easy to do even when you’re flying if you wear one of your jackets onto the plane).
They’re all different colors, and I pre-load each of them with a pocket square in the breast pocket.
I also stick some business cards in the pockets of each one — not a fashion tip, per se, but handy when you’re traveling from conference to conference.
My shirts are also chosen to be flexible.
I always bring one plain white dress shirt, and every traveler should do the same — it’s the ultimately versatile shirt.
You can wear it with a suit and tie, or you can wear it with blue jeans and roll the sleeves up, or anywhere in between.
The other shirts cover a range of patterns and colors that are easy to match:
Semi-solid light blue (with a herringbone weave to make it a bit more interesting), blue-and-white candystripe, and a dusky lavender with contrasting herringbone.
I also pack a short-sleeve linen shirt and guayabera in the summer, for when I want to shed the jacket and look casual.
I wear dark, fitted jeans when I travel, and pack a pair of lightweight gray flannel trousers and a pair of khaki dress slacks. Any of those can go with any of my suit jackets, for a wide variety of looks.
My neckties cover a good range of colors and all have pretty basic patterns — I keep it simple so they’re easy to match.
For shoes I usually have a pair of casual brown leather bluchers cap-toes, a pair of Sperry topsiders (slip-on boat shoes), and my Lucchese Western boots.
And here’s the total effect of all that - If you slim me down to my bare essentials, I have:
three pairs of trousers
two neckties, and two pairs of shoes
How many different outfits do I have?
A hundred and eighty different combinations.
Now, a few of those might look a little off, but by and large I can combine any one of my jackets, shirts, trousers, ties, and shoes and be in good shape.
Throw in three pocket squares and suddenly I’m at 540 different outfits — some of them might be pretty similar, but it’s still an incredible number!
4. Wear the bulkiest clothing
Now number four, wear the bulkiest clothing.
This one’s pretty quick.
I wear these boots, Lucchese 1883s. My jeans, they’re going to take up more space than my dress trousers; I wear them.
Also when I’m driving, if I spill coffee, jeans are very easy to clean up.
I always wear one sports jacket especially if I’m flying. I will take the jacket on. I can always have it hung up. The shirts, they’re all pretty interchangeable there, so pretty simple.
5. Secret weapons
These last few tips are a few tricks I’ve picked up over the years to making looking good while I travel easier.
They’re the product of experience and practice — over time, I’ve learned what works well for me, especially when I’m not only traveling but also presenting or doing business, and I need to look my best.
Wurkin Stiffs Magnetic Collar Stays – these go right into the collar if your shirt is built like that. You put the magnet under there and it keeps your collar points exactly where you want it.
Again, if I’m getting in front of hundreds of people or I’m talking to one person at a networking event, I don’t want to worry about my collar.
I don’t want to worry about the way I dress. I want to worry about making a deep and solid connection with the people I’m talking about.
These look less than masculine when you see pictures of them, but they work great.
They’re little elastic garters that clip to the bottom of your shirt and the tops of your socks, making sure the shirt stays tugged down and neatly tucked inside your trousers.
It’s a fantastic way to never have to worry about “muffin top” — the unattractive look of a guy with a lot of extra shirt cloth billowing out over the waistband of his trousers.
I use a set from Sharp & Dapper – they have lasted for over a year which is much better then cheap versions I’ve tried in the past.
RibbedTee undershirts makes an amazing V-neck and Crew Neck undershirt.
I use these all the time.
I double them whenever I’m going to exercise or when I’m going to work out.
I’ll just simply wear one of my undershirts.
Occasionally, I will take out my workout gear, but if I forget that, I’ve always got my undershirt. I could wear it around my hotel room, work in it, feel perfectly fine.
Those are my five points.
Let me summarize them again:
• Know your needs
• Protect your clothing
• Pack an interchangeable wardrobe
• Wear your bulkiest clothing
• Secret weapons
Hopefully you enjoyed this article!
If you want more information or if you’ve got some questions, make sure to leave questions. I love hearing from you guys in the comments section. You can also go check out my Men’s Style Q&A and post your questions there!