Packing Tales and Fails from a Maximalist Who Flies a LOT

In my humble opinion, the only thing more exciting than peeking inside someone’s refrigerator or bathroom cabinet is glimpsing the contents of their suitcase. For better or for worse, this humble vessel is essentially a TSA-enforced capsule wardrobe and beauty regimen combined, and the things you choose to include in it can be extremely telling. That’s why when Lillian Ahenkan, a.k.a. FlexMami, a.k.a. one of my favorite stylish people I follow on Instagram, told me she was coming to New York for a brief visit this month, I asked if Man Repeller could shoot her in three outfits she packed in her suitcase and pepper her with questions about how she contains her vibrantly maximalist fashion sense inside a container. Not only did she say yes, but she also raised the bar and pulled a veritable packing magic trick out of her proverbial hat by showcasing how she wears one staple wardrobe item (in this case, a bright yellow blazer) across multiple outfits when traveling. Keep scrolling to see the photos and read about everything from how her packing philosophy has evolved to her biggest travel disasters.

What is your philosophy when it comes to packing?

My philosophy for packing mirrors my philosophy in life: Excess is best. It’s a habit I’m actively learning to curb, but not fast enough given that I travel for work at least 2-4 times a month. By nature, I’m a big-picture thinker who likes to plan for all scenarios, both realistic and unrealistic, which means that strategic packing is not my strong suit. I pack what’s clean, what would make for a good photo opp and outfits that (from memory) make me feel my best, but I have a pretty poor memory which means I usually end up packing things I don’t quite like wearing, or that don’t photograph well.

Generally, for any trips between two and seven days, I’ll take one checked bag and one carry-on. For trips longer than a week, it’s two checked bags and an unavoidable (probably avoidable) excess baggage fee. Once upon a time, I would use a small suitcase as my carry-on, which in retrospect was completely foolish because I would overpack (see my motto) and then pay a hefty fine. I’ve since graduated to a humble canvas tote bag to hold my essentials – terrible on the shoulders and my hoarder mentality, but great for my bank account. As for my checked baggage, I divide the space into three parts:

1. Beauty

I pack at least nine pounds of skincare and makeup, which sounds absurd, but this stuff weighs more than you think. I would be lying if I said I only carried essentials; it’s mostly non-essentials and fun products I’ve never used — the result of my “beauty influencer” instincts that make me think I’ll film some content.

2. Clothing

Packing clothing tends to be the most frustrating and the most rewarding part of this whole experience: a combination of anticipating how good I’ll feel when I arrive at my destination with a suitcase full of potential opportunities to flex, and the awareness that I’ve probably packed too many items for scenarios that will never happen. For example, who packs a sundress on a vacation to rainy Toronto because it would be a great first date dress?! Or two pairs of cowboy boots so as not to be limited by the potential garishness of the white pair or the boringness of just black? Me. I do. (I know, I’m the worst – but also your fave.)

3. Accessories

A sensible packer would throw in a casual shoe, a dressy shoe and a practical handbag – but no, not me. Shoes are my kryptonite and the “wrong” shoe can ruin my day and my outfit for plenty of reasons. I’m a slow walker ( I call myself a waddler), which is exacerbated by the fact that I gravitate toward fanciful shoes (knitted mules) or painful ones (leather shoes I haven’t broken in). Generally, I pack about four or five pairs of shoes and only wear two. When will I learn?

Do you have any memorable packing-related stories?

One that springs to mind and causes me great distress to recount is when I was departing for a three-day tour (for context, I was DJ-ing Groovin’ the Moo, a traveling festival). I was scheduled to travel all across Australia, which meant I would be encountering really warm and really cold weather. Due to a scheduling mix-up wherein I thought it was Thursday when it was actually Friday, which meant I hadn’t packed ANYTHING and my flight was in three hours, I threw together a mishmash of faux fur coats, bomber jackets, little bicycle shorts and T-shirts – essentially a suitcase full of objectively bad outfits — and went on my merry way. When I got to the airport, my flight was delayed and I was stuck with a suitcase of impending doom. Thankfully I haven’t had any similar snafus since, and with every trip, I’m becoming a lot more discerning about the best way to pack for my lifestyle.

How does travel/packing in a suitcase impact your style?

Packing tends to illuminate the contrast between the “projected version” of me that prioritizes aesthetic over comfort and the “real version” of me that loves outfit repetition and predictably amazing looks. There’s nothing worse than test-driving a new outfit on a trip and being surprised by a wrap skirt that blows too far in the wind, trousers that ride up into your crotch or a shoe that ends up rubbing. (Luckily I’m getting closer to finding my “uniform” — the outfit combination that makes me feel my best and ticks all the boxes, like increasing my self-esteem, working for various occasions, being the perfect blend of functional and aesthetic, etc.) When I travel, my outfits are dictated by daily activities and how I want to be perceived; color means I’m open to socializing, black says otherwise.

Do you have any staple wardrobe pieces you won’t travel without?

I usually pack three blazers — a black one, a brightly colored one and a wild card option. Having these staples in my arsenal is useful for creating multiple different outfits. Styling a yellow blazer three times in three distinct ways for the photos that accompany this story is a testament to this fact. I prefer an oversized fit because it gives me the ability to lean really casual or super put together.

As for other go-to packing pieces, I try to bring a pair of well-fitting trousers that alleviate the effort of putting together an outfit because they just…work.

What advice would you give someone who consistently overpacks?

You know how people advise you not to wait until the day before a special occasion to try a new hairstyle or makeup product? I think that is a valuable mindset to apply when packing. Trips probably aren’t the ideal time to whip out an untested wardrobe, unless you’re prepared to spend a lot of time getting ready. Save yourself the frustration and, when in doubt, follow Leandra’s methodical carry-on approach. Other than that, pack what the current you would wear day-to-day, not what the romanticized version of you would wear. And check the weather app – sounds obvious, but you never know when an unexpected rain storm might be brewing.

Photos by Edith Young. 

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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