The Best TSA Friendly Shoes

Laura Lopuch

Like good cowboy boots, the best winter shoes are crafted of quality leather with a good sole. They also require a bit of breaking-in to soften up that hard leather exterior. Once you’ve worked the kinks out, those shoes will gladly tramp through all your adventures come snow, sleet or rain.

However, the only hiccup is those best-friend-shoes might not be ideal for trekking through airport security.

All those laces to untie and re-tie. That touching-my-knee height. Pull-on cowboy-boot-style makes me hop like a demented rabbit. Oh my.

I’ve got ya covered. These shoes were made for walking and are TSA friendly. They’ll get you from curbside drop-off to airplane gate quickly and easily.

Top 5 Fall & Winter TSA Friendly Shoes

  1. Lock laces: swap out the laces on your usual sneakers — my best traveling shoes, always ready for a dash to the airplane — for these bad boys. Forget about tying laces after security. Slip your shoes on, pull the lock to tighten your laces, and you’re done. Easy, peasy.
  2. Loafer or ballet flats: You pop them off, stick them in the TSA bin, and grab them after the scanner to slip back on your feet. Women, try SoftWalk Napa ballet flats ($99). Men: check out Cole Haan Howland Penny Loafer ($170).
  3. Boat shoes: Men, opt for Jack Erwin boat shoes ($125) with reverse lining for gripping your heel, leather, and non-slip soles. Oh — and they’re easy to kick off. Women, here’s your version ($65).
  4. Chelsea boots: Iconic, flat boots with a bit of stretch so they pop on and off your foot smoothly. Women, try Aldo Scotch ($120). Men, go for Keen Tyretread ($140).
  5. Toms Shoes ($55): Canvas. Comfortable. Ready for a quick dash for a departing plane. They’re your best friend through security.

Wear This, Pack That

This section is for those tricky trips where your shoe needs battle against each other.

These situations crop up whenever your comfort and your trip’s intention or location (i.e. wedding, or warmer destination) conflict with each other. Welcome to standing frozen in front of your closet for long minutes, debating the pros and cons between Those Shoes and These Shoes.

To blister, or not to blister? Aye, there’s the rub.

You need a comfortable walking shoe to protect against those hard cobblestone streets. But, you also need a shoe that doesn’t leave you struggling to untie your laces in the TSA line.

This section is for you.

Note: Most of these situations assume you’re in the Northern Hemisphere, entering into crisp fall and cold winter months.

Wedding, Party, or Festivities for Festivus

Christmas, New Years, perhaps a glittering wedding; winter holds many opportunities for a party and a chance to shake off your dancing shoes. However, this type of trip means taking another pair of (party) shoes. Here’s what to bring.

Wear Through Security

Women, a cute but dressy Mary Jane is your best friend in this scenario. They’ll pull double-duty for you.

With a low heel and one-strap, this shoe is easy to navigate through TSA and the airport. Plus, it’s dressy enough to look at home with a dress (for the rehearsal dinner or cocktail hour) or with jeans (hello, hotel or dive bar). Check out Naot Footwear Pleasure ($175).

Men, a handsome leather loafer will take you far. Snazzy enough for jeans or black pants, yet comfortable and slip-on to make TSA a breeze.

Even if you’re speed-walking for your gate, your dogs won’t bark in protest. Check out Cole Haan Howland Penny Loafer ($170). Reviews boast of this shoe’s lightweight comfort.

Pack This Pair

Women, forget about spike heels and go for a sexy wedge. It hogs a little more room in your bag, but your feet will thank you. (Stuff each shoe with socks to make good on that space and help your shoes keep their shape.) Michael Kors Damita Wedge ($99) is a highly-rated option.

Men, a beautiful oxford is your best friend. Hankering for an old -fashioned shoe to sip mint juleps in? Stacy Adams Madison ($120) is your answer. These beauts rates 5 out of 5 stars from Zappos’ killer reviewers.

Business Trip

Wear Through Security

Women, go for a classic ballet flat. Check out SoftWalk Napa ($99) for cushioned comfort in a polished black. The leather gets softer every time you wear them. (I know from personal experience; these are my go-to shoes.)

Men, opt for a leather loafer like Hush Puppies Leverage ($135) or Bostonian Capi ($110) with breathable leather and two pods of cushioning under the footbed. My husband wears these to work — he’s on his feet 10+ hours/day — and swears by their comfort.

Pack This Pair

Women, go for your classic nude or black heels like Clarks Delsie Bliss ($65-120). They have an ortholite insole, supple leather, and rubber outsole for slip-free walking.

Men, go for black or cognac oxfords. Try Rockport Syle Purpose Cap Toe ($120) for old-world brogue detailing and handsome leather.

Cold Weather Destination

Wear Through Security

Short motorcycle-inspired boots with decent tread and good arch support are TSA friendly. Pack merino wool socks in your carry on and you’re set for any kind of weather.

Women, check out Frye Vicky Artisan Back Zip ($200) or go for these Rockport combat boots ($160) with a cushioned insole.

Men, see Red Wing Black Side Zip Motorcycle Boots ($130). Let me list the ways I love these: water-resistant leather uppers, extremely tough, repairable soles if you destroy them, and high resistance soles with a meaty tread.

Pack This Pair

Women, Clarks Janey Mae ($110) are perfect if you’re an older traveler. They’ll keep you safe and comfortable on any surface, even those icy sidewalks. Or, if you’re in the boot-mood, opt for Frye Melissa Button Back-Zip ($142+) and rock the classic riding boot look.

Men, waterproof Rockport Oxford-inspired shoes will keep you warm and dry. The handsome leather and style will take you from mountain to steakhouse. The under $100 price keeps your wallet happy.

Warm Weather Destination

Wear Through Security

If you want slip-on-easy and casual shoes, look no further than Toms‘ original canvas shoes, a big travelers’ favorite.

While I’ve never worn them, fans rave about their comfort. Score one for being TSA friendly. With a non-slip sole, you won’t be skidding over slick airport floors, racing for your flight.

Pack This Pair

Ah, beaches and sunshine call for sandals. If your warm weather trip involves a considerable amount of walking, go for sturdy Birkenstocks ($99-160). With their iconic two straps and a shock-absorbing sole, your foot is stable and comfortable. Here’s the unisex version.

If all your walking is from Airbnb to beach, go for flip flops.

Sanuk flip flops are the ones I love; almost 5,000 Amazon reviews gave this flip flop a 4.5 out of 5 stars. The footbed is made from yoga mats, so your feet are walking on layers of cushion. Beware: the footbeds can get slippery when wet.

Women, here’s your Sanuk ($32). Men, here’s yours ($17-42).

Walking Destination

Wear Through Security

Women, you have a plethora of options. Thank the fashion gods that cute and comfortable are no longer mutually exclusive. Opt for ballet flats with a cushioned sole and classy style for dining out or nights at the opera.

Check out:

  • Cole Haan Women’s Air Monica Ballet Flat ($117-200): One Amazon reviewer said, “Classy, classic and reasonably comfortable for someone who walks 5+ miles a day.” Beware: these flats take a while to break-in due to their high-quality leather.
  • Josef Seibel Women’s Pippa 07 Flat ($65-115): Premium leather, dual air-reaction insole, and durable rubber outsole. Heck yeah. One reviewer raved, “Comfortable. They remind me of the expensive French brand of shoes in their look.”
  • Cole Haan Zerogrand Stagedoor Stud Ballet flat ($140): Deceptively thin-looking, these chic leather flats have a full rubber outsole with Zerogrand technology (Cole Haan’s new version of Air technology) for your supreme comfort.

Men, Under Armour SpeedForm Apollo 2 ($75) has you covered. They hit all the tick marks: Easy to slip-off, sophisticated black color, pairs well with shorts or jeans, ready to hit the gym, and dry quickly if they get wet.

Pack This Pair

Your favorite sneakers, all broken in with tread left on the bottom. If you’re strolling Europe’s hard cobblestones or China’s miles of cement, you’ll want shoes that you:

  • Don’t have to break in already
  • Can hold up to long days of trekking, exploring, and wandering

I know the cliche of tourists in sneakers, but trust me, you’ll want sturdy, comfortable shoes on this trip.

Women, check out New Balance Fresh Foam Hierro ($115) With a foam midsole and exceptional traction, you’ll battle cobblestones and 10+ mile days easily.

Men, you’ve got it easy. Just bring one pair of shoes: the Under Armour.

With their discrete black color and no flash, you can wear them to a nice dinner out. Granted, you won’t be able to pull off a ballgown and tuxedo event in these shoes… but that’s a packing list for another post.

MVP Additions

Did you buy a pair of shoes that you love, but they’re lacking in arch support? Or, maybe the balls of your feet are aching?

Spring for a pair of insoles and make your piggies happy:


When traveling in the fall and winter months, opt for leather and a sturdy, non-slip outer sole for your shoes. To make your shoes TSA friendly, look for slip-on or zippered styles.

Your best bets are:

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