building a travel wardrobe 01 // bag edition

confessions of a packing procrastinator

I love traveling, but hate packing. Packing is probably one of the most challenging exercises in editing your personal style. Travel’s unforgiving demands strip everything down to dealbreakers. Can I really walk in these all day without blisters? Can this bag handle being shoved under a plane seat and tossed into those filthy TSA trays?¹

Since my college days, I have always been a night-before packer (not smart, I know), and every year I resolve to reform (getting there!). During a late-night packing marathon two years ago, I realized that the reason why this always took forever was the selection of the clothes, shoes, and bags. I’d spend way too much time drafting my packing list, and then it would inevitably devolve into a tug of war between things I’d think I’d want to bring vs. what I would actually choose. Add in extra time for outfit try-ons to confirm fit and style, and, well, suddenly it’s 9pm and a mad rush to finish before a crack of dawn flight the next day. Without fail, my comfort zone, tried-and-true travel go-tos would always win—a classic case of utilitarianism triumphing over aesthetics.

A big part of my personal style journey over the last decade has been accepting that I’m a pragmatist at heart. That said, I’m always on the lookout for ways to elevate my travel essentials. Feeling good about what I’m wearing is such a mood booster, and I can definitely use more of that while dealing with the stress and indignities of flying commercial.

After lots of trial and error, my rule for travel bags is keeping it to 3:

1. a large (but not so large that it can’t go under the plane seat) “personal item” carryall for the flight (I don’t check luggage unless absolutely necessary, so this bag needs to help maximize space in my carry-on.)

2. a medium-small (roomy but still relatively compact) bag for sightseeing, day trips, etc.

3. a small bag with a strap for anything dressier at night, restaurants, shows, etc.

i. large in-flight carryall (Anya Hindmarch, a lucky sale find from 2015 – AH now makes an ingeniously organized travel bag just for this purpose!) // ii. medium all-purpose day bag (Longchamp, purchased in 2018) // iii. small crossbody/clutch (Botkier, another great sale find from 2017, sadly discontinued)

I pack my Longchamp medium pliage as my main day bag 90% of the time—it’s light-as-a-feather nylon, folds flat into a tiny square, all black, and zips up on top. It’s ideal for all day touristing because it’s the perfect size, weather-proof, and secure by design. More importantly, it’s anonymous. (Depending on where you’re going, this stealth factor can be essential for your personal comfort and security.)

This got me thinking: what can my road-tested travel essentials teach me about my everyday wardrobe? (A lot, actually.) Are there key takeaways from my preferred travel accessories that should fundamentally inform how I shop? (A resounding yes!)

I made a shortlist of reasons why I always pack what I pack and found some recurring themes:

• comfort (ergonomic design, lightweight, convenient carry options)

• neutral colors (I find certain colors mentally soothing, and neutrals make maximizing outfit options with very limited space infinitely easier)

• minimal styling (no logos, clean lines, no superfluous embellishments)

• carefree (that priceless feeling of being completely at ease so you can focus on being present and enjoying the actual trip)

This mini wardrobe editing exercise also reminded me that while packing for my last few trips, I kept wishing I had a bigger hands-free style small bag (one size up-ish from the convertible clutch) that could also pack flat like my trusty Longchamp.²

So, inspired by these travel capsule insights, last month I bought two very The Row-esque bags at a fraction of the price: a COS leather crescent crossbody (in a lovely dark chocolate brown) and Uniqlo’s off-white nylon version. Price point, comfort, design, space—they check all the boxes. In addition to travel, the Uniqlo one will be used for workouts and quick errands. (I avoid light-colored leather bags because life’s too short to deal with color transfer, so this will be an easy spring/summer option that can be wiped clean or washed if necessary.) The COS bag is an elegant update to the fanny pack genre: buttery, soft leather that contours well to the body when worn,³ a comfortably wide shoulder/crossbody strap and—bonus: deceptively roomy with a top zip opening that’s easy to get in and out of (I can fit my Kindle!). Both add something new and needed to my existing rotation for travel and everyday. If you’re looking to buy an inexpensive but stylishly versatile small bag for this season and beyond, I recommend these.

Giving off The Row vibes but saving you that chunk of change so you can put it towards your next vacation.

What are your essential travel bags? What do you struggle with when packing?

N.B.: Keep a notepad nearby when packing so you can jot down any pain points or wardrobe needs. Even better, take note of things that are wanting or lacking during your trip. This kind of lived experience note-to-self will be invaluable when you make your next wardrobe wishlist, and more importantly, will make future travel more enjoyable!

1. I always bring one or two Baggus (reusable, washable nylon totes that I also use for grocery shopping) and will sometimes use one as an outer shell to protect my in-flight carryall from scuffs and conveyer belt gunk when going through the security check. I’ve had them for well over ten years and periodically throw them in the washing machine and hang dry, and they’re still good as new.

2. Flat-packable bags are a godsend, especially for suitcase-based travel.

3. It took me some time and a few purchase mistakes to realize that structured bags that are a) very bulky and b) protrude awkwardly when worn are bad buys. A supple shape that sits well on the body makes all the difference in how often I’ll reach for it.