Travel fashion Q&A with Samantha and Aldo

Travel fashion

Both Aldo and I travel a lot. He does much more than me, especially with his work. I frequently visit New York, and once or twice a year I go somewhere for holidays. We’re both admitted light packers. I only started in the last year and a half, because solo travel and carrying around heavy luggage didn’t appeal to me after doing it once. Aldo is a light packer by nature.

Neither of us checks luggage unless it becomes necessary. Airlines allow you to bring a carry-on bag and a personal item such as a laptop bag, purse or backpack. We both take one carry-on and one personal item for trips up to two weeks. Well, Aldo can do it for three weeks, but I haven’t tried it yet. I’m not sure I can get there!

People have asked us how we do it and manage to look stylish when we’re away. So we decided to do a joint Q&A about it. Like our first Q&A post, my bestie Carrie interviewed us.

Overall tips

Question: What type of luggage do you take with you?


Travel bags 
I carry a large flexible bag like the Odette travelers bag I just got from Zaimara and a gold laptop bag with compartments from Coach (the gold is a standout in person). I fit a purse or two in the laptop bag, and I pack my makeup and other personal items in my purse, so it’s not empty just taking up space. If I’m only bringing one, it’s small to mid-sized so that it can function day or night (there’s a picture of it near the bottom of the article).


Tumi Bags

Tumi backpack that can hold a laptop and a carry-on that can hold suits

I take a backpack and carry-on. Backpacks can hold a lot more than other personal bags and will still fit under the seat. I use Tumi because I find them durable and they have a laptop protector. It is expensive, but I travel more than 150 days a year and have gotten my return on the investment. Skywalk makes similar bags for much less, and I have heard good things.

Question: What are your overall clothing packing tips?


Tumi Carry-On Suit Bag Packed

My carry-on suit / laptop bag packed

Pack a week’s worth of clothes. If you’re going for a couple of weeks, you can wash them in your room and hang them to dry or pay for them to be cleaned. Pack clothes that coordinate with everything you’re bringing. If it doesn’t work in multiple outfits, don’t bring it. Think of what you can do without, not what will be handy. I suggest taking two pairs of shoes, the type depends on your trip, and two pairs of pants, and wearing your heaviest items on the plane. Bring a reversible belt, black on one side and brown on the other so you can wear it with anything you need, Amazon carries a lot of brands and styles.



Travel outfit city

Taking a break from walking in my Zaimara dress, jacket and travel bag

I agree. I’ll wear one pair of pants on the plane depending on the weather, but I tend to stick to dresses that don’t need to be ironed, like jersey material, or ones that look fine if they’re slightly wrinkled. That would be my number one tip for women. If you don’t mind wearing dresses, I’ve found them so much better for travel. They take up less space than pants and shirts. You also don’t have to coordinate tops and bottoms, so it’s less work! And, they can be dressed down during the day or up at night with some small accessories.

Question: What do you wear on the plane?



Style, form and function with these boots and leggings. Photo in New York last year during my stay.

I wear the clothes that take up the most space and are comfortable. So if it’s cold in Toronto and where I’m going, I wear a jacket, sneakers, leggings and a shirt.  If it’s cold where I’m heading, I wear stylish high boots with a flat heel that can double as something I can wear out at night too like shown in the picture. These boots are comfortable to walk in for hours too so that I can wear them all day long. If it’s warm, I wear a maxi dress.

I don’t have much else to add since I also wear the clothes on the plane that take up the most space.

Question: What must-have clothes do you pack?


Girly slip on shoes

Girly slip on shoes by Naturalizer

Comfort and convenience are key for me. For a week or two, I go in leggings and as I mentioned, dresses that don’t wrinkle. I don’t want to waste time ironing anything, ever! I always bring a workout outfit and two pairs of shoes, sometimes three if I can squeeze in an extra one (one of these I wear on the plane). Unless it’s a special occasion, I only wear flats when I travel. They take up way less space. From May to September, I find ballet flats are travel-friendly. They’re also fine to walk around in and look good with almost everything. I have Girly slip on shoes from Naturalizer in multiple colors. Amazon carries them. The other months I wear high boots with a flat heel.



Light jacket, Calvin Klein sweater and reversible belt from Ted Baker

I follow my first tip. I bring two pairs of shoes; one I wear on the plane. One will be a pair of sneakers so I can work out and walk around. The other will be either dress shoes or casual, depending on my trip. I take two pairs of pants or three pairs of shorts, five shirts of varying weights depending on the weather, and workout clothes. For shirts, I tend to stick to Calvin Klein t-shirts or their slim fit Infinite shirts because they are comfortable and don’t wrinkle. I also bring a reversible belt and I’ll also wear a light jacket on the plane in case it rains or gets cool at night, like this one shown in the picture. Old Navy has similar styles. I bought this years ago!My style is always somewhat casual, so to travel I don’t have to change much to be able to go for hours. If one of the pants I have to bring must be dressier, like for work or an event, I will make sure the one pair of jeans I take with me look good day or night.

Warm weather trip

Question: What are your essentials to keep cool and look good at the same time?



Wrap/Cover-up in Cancun

Maxi dresses and sundresses. For a week I can fit five or more dresses into a bag at least, and three bikinis that I’ll wash and hang to dry. I pack one workout outfit, a cardigan if it gets chilly at night and a beach wrap that can double as a full cover-up like shown in the picture. Amazon has lots of them. Beach shoes and a pair of decent looking flats are all I pack, and I’ll wear my sneakers so I can also use them to workout.



T’s are easy to pack. Rolling them stops them from wrinkling and you can fit more.

I have a similar approach to Sam, it’s easier to pack warm weather clothes because they’re lighter and take up less space. I still wear jeans on the plane in case there’s a night that you need them, but can usually fit five-seven shirts, three-five pairs of shorts, the same amount of swim shorts and two pairs of shoes.

Special occasion trip

Question: How do you pack if you’re going to an event like a wedding, or on a cruise?


I can still get away with using my bags I typically bring. I may swap out the laptop bag for another large bag that looks like a purse since I mostly likely won’t need a laptop. I will wear a jersey dress shown in the picture from BCBGMaxazria because it does not wrinkle. I have traveled with this to two weddings over the years, and it comes out of travel still looking spectacular. Lulus has some great jersey occasion dresses from mini to maxi at good prices.


Tumi Carry On Suit Bag

Carry-on suit bag from Tumi

To pack a suit I use a carry-on that doubles as a folding suit bag and has some compartments (Skyway carries one). It helps me pack my other things in it as well and then I’ll bring another bag that can fit under the seat with everything else like my dress shoes. I turn my suit jacket inside out so that if anything happens, it’s only the inside that is affected. Another tip that I mentioned earlier is to bring a reversible belt. You can wear it with anything. Depending on where I’m going for the event and the cost, I may rent a suit there, so I don’t have to carry one. To do it, I have to set it up before I leave (the time depends on location), know my size and fit in the brand, and what to do if it doesn’t fit.

What a great idea! I never thought of renting an outfit in advance instead of bringing one.

Business trip

Question: How do you pack for a business trip?


calvin klein infinite

Calvin Klein Infinite shirt

I wear similar clothes as I do for a special occasion. I will need at least one suit, dress shoes, and a belt, plus my shirts. Calvin Klein Infinite dress shirts don’t wrinkle. Amazon carries them plus other brands that don’t wrinkle at different prices. I have to take a laptop in this case, so I have less space for clothes. I will usually go with lighter shirts like t-shirts and then wear the jacket that I wore on the plane if it’s colder.


Suit and laptop

Suit and laptop in bag

I wear suits for business meetings usually. I can fit a suit into my regular travel bag. I’ve even been able to fit it in with my laptop in that bag. Because that’s the bag I keep under the seat, I can check to make sure my suit keeps its structure, unlike when it’s crammed in the overhead compartment. If I need more than one suit, I switch to my Heys hard case leopard print carry-on, so they don’t wrinkle. Walmart has it plus others at various prices.

Cold weather or potential bad weather trip

Question: What travel essentials do you bring for cold weather, or if it rains?


Winter Toronto
I bring layers rather than take a thick coat. The same T-shirt that I wear when it’s warm can be worn as a layer when it’s cold. I pack less of my heavy layers. Sweaters or thick shirts can be worn more than once if you change the shirt closest to your skin. I bring a fitted hat that can fit in a jacket pocket  in case I need it.


purse + umbrella

9-inch (22.86 cm) purse and umbrella

I would just add that I carry a small umbrella. I have what I call my “Wile E. Coyote” umbrella, and it fits into anything. It shelters me enough from actual rain too! I’ve had it for five years, the best $10 I have ever spent!


Couldn’t resist adding in a photo of Wile E. Coyote and his umbrella!

Last question

Question: Any final tips you want to share?

Keep to your style but stay comfortable.

I just want to reiterate that Jersey material is your best friend on a trip! It works whether the dress is flowy, fitted or wrap-style depending on your preference.

These are some of our travel fashion tips. What are some of yours?

73 replies »

  1. Practical tips from both. My wife learned a lot she said! I haven’t heard of Skywalk brand. Thanks for sharing. I am looking for something more durable. I also never thought of renting a suit before instead of bringing it. I have to look into that. Valuable info you provided!

    Liked by 2 people

    • Thanks a lot! Renting a suit is good. Do your research into how long in advance you need to book it, what happens if it doesn’t fit (would they have backups in your size). I try on brands that look good off the rack and go from there.


  2. These are awesome tips! I do get fussed over matching clothes so I bring more so I get your point about dresses. I guess jumpers and jumpsuits would do the same. Thanks for sharing these!

    Liked by 1 person

  3. Great job both of you! How you manage to fit a suit in a laptop bag I’ll never know! And what a great idea to rent something instead of carrying it if you know what your exact size is. I tend to take too much with me so this is appreciated. Love the QA style too

    Liked by 2 people

  4. This is awesome! Thanks for sharing . I find these tips helpful . Agree about dresses being easier to pack. Happy Weekend too👌


  5. Thank you to both of you for the packing tips. My question for both of you is which type would you recommend to bring. I know it depends on the type of the trip. I usually bring a pair of casual, dress and athletic shoes.

    Liked by 2 people

    • Thanks Marko! I usually bring athletic shoes that can function day and at the gym and one other pair depending on what else I need to do so either semi-casual, or boots if there’s a lot of snow or dress shoes.


    • Thanks so much! I bring sneakers so I can work out and sometimes to walk in and 1 pair of flats or boots depending on the temperature. If it’s a special occasion I’ll bring one extra pair of shoes.


  6. Thanks for the tip about Calvin Klein Infinite shirts. These are all great tips. I never thought about renting suits away but I have a tough body type to fit! I get the idea as long as I know my fit in a brand it would be easier. Thanks for sharing!

    Liked by 1 person

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