I love, love, love to travel but I refuse to waste a single moment waiting on luggage at the baggage claim once I reach my destination. No matter where I’m going or far how long, I see it as a personal challenge to pack everything I need in a single carry-on suitcase and a bag that fits under the seat in front of me. Of course my plan is occasionally foiled when I’m forced to gate check my suitcase but at least then I know I did everything I could!

how i pack my carry-on suitcase

I decided to snap some pictures while I was packing for our trip to Nantucket so you could see my packing strategy in action and I could share a few of my carry-on packing tips. I almost always use this Steamline luggage — Will gave me this navy carry-on for Christmas two years ago and it’s truly one of my favorite things I own. People always comment and ask if it gets dirty — mine definitely isn’t spotless but I do take good care of it and most marks (especially on the white leather trim) wipe off pretty easily (I’ve even used my makeup wipes in a pinch!). It’s such a vintage-inspired suitcase that a few scuffs and scrapes don’t bother me! If it’s something you’re worried about, Will has the hunter green version with tan leather trim and his definitely shows less wear! And if it’s something you’re really worried about, this set gives you a similar leather trim look but with a more durable body.

design darling steamline luggage entrepreneur

My biggest piece of advice is to plan out your outfits in advance. Even if it makes you feel like you’re prepping for your first day of high school, it’s such a helpful way to get organized. I used to pack a pile of tops and sweaters next to a pile of jeans and shorts and call it a day (“I’ll see what I feel like wearing when I get there…”) but now I try everything on before it goes in the suitcase to make sure I have as many complete outfits as I’ll need for however many days I’ll be traveling.

design darling carry-on packing tips

Obviously I might mix things up once I get there but it’s nice to know I’ve packed the right number of items and can then make any game time adjustments if I’m so inclined. I typically pack twice as many tops as bottoms just because it bothers me more to repeat a top (especially if I’m on a trip where I’ll be taking lots of photos) than it does to rewear the same pair of jeans.

design darling carry-on suitcase packing tips

My second piece of advice is to pack your pajamas first so they’re at the bottom of your suitcase. This might sound strange but knowing I’ll need my pajamas soon after I arrive at my destination forces me to unpack the rest of my suitcase the same day I arrive. I’ll hang what needs to be hung and lay out other items on a surface in the room unless I’m staying long enough to actually put everything in drawers. It’s also a good way to avoid excessive wrinkling and remember what you packed in the first place!

carry-on packing tips

I also try to minimize the number of bags and shoes I bring as these take up the most space in a suitcase. I think it’s a good idea to travel in a pair of shoes you’ll want to wear on your trip and then pack any additional pairs in your suitcase. This is hard to do if you’re travel from a warm to a cold location or vice versa but it definitely saves space if you’re trying to make cuts.

design darling navy suitcase

Personally, I’m not a huge bag person so if weren’t for taking outfit pictures while I travel and not wanting to bore you all with the exact same accessories every time, I’d probably stick to a suitcase, a carry-on handbag, and a single clutch for nights out. You might substitute the handbag for a beach bag if you’re heading to the beach or swap out the clutch for a cross body bag if you’ll be doing a lot of walking in the city.

carry-on packing tips design darling

I’ll admit that I tend to bring the largest possible second carry-on, which during the summer often means a boat tote or oversized straw bag. Another good option is to carry a small duffel bag and then pack your handbag inside it with a few other essentials. I like to have easy access to my cosmetic case if I’m on an early flight and don’t do my makeup until I land, plus it’s light enough to carry in a bag instead of in my rolling suitcase. Then I’ll fill it up with my laptop, camera, phone, headphones, wallet, sunnies, etc. and I’m good to go! My carry-on is a lot lighter since switching to Audible for most of my reading — obviously it’s nice to purchase hardcover versions of your favorite books and the classics but I highly recommend it if you’re tired of lugging around beach books you’re only going to read once.

design darling steamline luggage carry-on packing tips

I wouldn’t say I have packing down to a science (I’m not one of those people who roll all their clothing, I wish!) but this works pretty well for me on most trips! Would love to hear your packing tips in the comments and let me know of any similar posts you’d like to see from me!

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  1. Love these tips…my family does the same thing! Was wondering where your nude wedges (pictured above) are from? Thanks!

  2. I have a question that I am genuinely interested in. You stated that you’d probably only bring one bag if you didn’t have a blog and posted lots of pictures, and I have to admit when I saw all three of your small bags it seemed like a lot. I recently found a blog where she had gone to Ireland and said something similar- if she wasn’t posting Instagram pics of her trip she would have dressed in something like all navy and gray, but because of her blog/instagram she picked different colors and packed more. So my question would be, how do you balance this in your life/work? Where is the line between doing something that you’d do because it’s who you are and doing something because you feel obligated for the blog? I know that for many the blogs are their job and I think that’s great and would love it myself, but it seems like a lot of pressure put on you.

    1. Hi Jess! On my blog I’m very true to my personal everyday style, to the point that I occasionally receive negative comments about wearing too much navy blue or too many stripes, etc. But I know I can’t please everyone and I can always see the difference in photos of myself wearing outfits I’m not as comfortable in. The way I see it, bringing a couple extra clutches in my suitcase is something a lot of girls would do (not just bloggers) and while for me personally it’s something I’ve started doing as a result of my blog, it’s a small tweak that hardly feels like an obligation and certainly doesn’t compromise who I am. Of course I feel pressure to look good on my blog, but I think most women (and men) feel that every day, regardless of their chosen profession. I’m sure there’s a line somewhere (for me it might be posting skirt suits to wear to work or wearing riding boots when it’s 100 degrees in Dallas) but I like to think I keep it pretty real. Thanks for tuning in! 🙂

  3. Mackenzie I’m a daily reader and love your blog!!! Where is your monogrammed toiletry bag from if you don’t mind my asking? PS love all of your other essentials, great post!