3 Travel-friendly Dresses for Petite Women Who Prefer Flat Shoes

I used to wear heels all the time. Now I avoid it if I can. Even though I’m only 4’11” the pain isn’t worth the price. This Orange County girl’s motto is now, function over fashion. And while traveling, in particular, going with flats makes sense – traversing uneven sidewalks, walking uphill and downhill, etc.

I think everyone has received the memo by now…flats don’t mean compromising on cute. Especially when paired with a dress.


Over this year I’ve added a few different dresses to my wardrobe. I focused on:

  • variety of style
  • packability
  • comfort

These are the 3 dresses that I love traveling with:

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MICHAEL Michael Kors petite maxi dress: $84 on sale at Macy’s
BCBGeneration: $15 on sale at Macy’s (no longer available in this style but they have it in a different style.
Maison Jules Fit & Flare $38 at Macys. No longer available in this style but they ALWAYS have cute fit & flares, like this one.

There’s a maxi dress, an A-line, and a fit and flare. I bought all of them on sale at Macy’s. Side note: in my opinion Macy’s has petite-friendly brands, carries nice styles, pretty good quality and has reasonable prices. And these dresses are all VERY travel-friendly. They don’t wrinkle, they fold compactly and are pretty light.

{Yes Shawty! You Can Wear Maxis Too!}

I have literally never owned a maxi dress before. This is my first one and I LOVE it. I always thought I couldn’t wear maxis because of my short stature. But I realized that it’s just a matter of finding one that has the right cut and fabric for my body.

And fellow (shawty) shorties finding that is NOT easy. I scoured the websites of Nordstrom, Anthropologie, White House Black Market, Macy’s, Ann Taylor, Bloomingdale’s, Old Navy, Athleta, and Target and this was the ONLY dress I found that:

  • fit
  • didn’t have a super plunging neck and back line
  • didn’t have spaghetti straps
  • and had a design that wasn’t just common stripes or humungous flowers

Those were my criteria, of course yours will probably be different. But I wanted something that I could wear casually as well as for work.

I bought the petite-small (I’m 4’11”, 100lb.) and had to get several inches hemmed from the bottom. I  recently wore this on a short flight from San Francisco to San Diego and was so comfortable. I’m usually really cold on planes, but the length kept my legs warm and I wore a light jacket on top. Plus it was a short flight, during mid-August – not the middle of winter.

{The A-Line Dress}

I love the sleeves on this A-line dress. They’re fitted and not too short. I happened upon the jewelry set a few months after I bought the dress. It matches really well with this dress but because it’s plain navy blue, I can wear it with so many things.

I also like that the length is above knee so in Fall and Winter I can pair this dress with leggings and boots and wear it like a tunic. This dress has so many colors in it and I already own a few plain colored scarfs that would look cute for winter as well.

{Above the Knee Fit & Flare Dress for Flats}

This Maison Jules fit and flare dress is flowy. It’s really a spring and summer dress. It’s incredibly comfortable and SUPER light to pack. I love wearing it with a belt which just gives it that finished look. In general, fit and flares are flattering on petite women and I personally always go for ones above the knee that look great with flats.

I see so many cute below the knee and midi dresses but I’d have to wear heels with them.

{Ladies, Travel + Bloating Is a Thing}

These three dresses have other travel benefits too: they’re all machine washable and….forgiving. Channeling my inner Maggie Q, I’m referring to bloating. It’s a common thing, especially amongst women. When you’re eating every meal out, and a lot of rich foods, and perhaps bigger portions than normal…or you’re simply you’re on your monthly – bloating is a thing and all 3 of these dresses hide it.

{Traveling Light with Pairings and Accessories}

I like feeling and looking put together while traveling. But I also prioritize traveling as light as possible AND not buying an entirely new wardrobe for every single trip.  So when I buy clothes (and I think most women do this), I think about what I already have in my closet that can go with my new items.

For instance, I have a light jean jacket that I can wear with all 3 of these dresses – so when I’m packing, I can carry one light cover up instead of 3. I can also take one pair of shoes to wear with all 3 dresses.

In the photo above I am wearing flat Aldo sandals and I also like the sparkly silver ballet flats too. Similarly the jewelry set I’m wearing in the A-line dress photo, can work with all 3 dresses. With the maxi, I tend to wear earrings only and maybe a bangle – sans that 3 strand beaded necklace. And alternatively I can pair the fit & flare dress with a fitted silver belt and silver earrings. The accessories are minimal, easy to pack but really give a finished look.

{Travel Purse-Bag From the A-Line Dress Photo}

As for the bag, I’m wearing in the A-line dress photo, you can’t really see it but it’s a Kipling crossbody. Crossbody bags are fantastic for travel – for obvious reasons. But I find it hard to find a crossbody that fits a lot of stuff but doesn’t look humungous on me like the other Kipling bags below.

Vertical oriented bags, like the one on the left, are unflattering on short women (IMO). And wide bags, like the one on the right, look frumpy, in my opinion.

Enter this Kipling crossbody bag – also from Macy’s. I bought this in red and black and have really enjoyed it. To be clear I wouldn’t use this for a whole day out walking around a city. For that I’d want either a backpack or something bigger that can hold my DSLR and a water bottle. But for evenings out or just walking down the street from your hotel for a quick bite, these are great from a style and carrying capacity perspective.


Left: me with the rounded, frumpy bag. Right: me with the horizontal bag.

{Use Cases For This Crossbody Bag}

I wouldn’t take this Kipling bag to London, Paris, Sydney, Cape Town or other bustling big cities. For that I’d want something bigger that offers more security like a Travelon or the women’s Soho Ogio backpack.

But I would take it to Hawaii. I would take it for a weekend in Orange County and traipsing around Caye Caulker. I would take it as an evening bag for dinner at my safari lodge. Basically it’s a great bag for scenarios where you’re not going to carry your DSLR, nor your water bottle and you want a refined look in an attractive bag that can carry your phone, wallet + tablet, sunglasses and other essentials AND keep your stuff organized with lots of pockets.

Bonus points that I know, not everyone cares about, but some do: these bags are not leather.

Regardless of the material, I think it’s important to note the application of the items that I recommend.

For a more detailed review of these bags and why I think they’re great for traveling petite women, click here.

{Side Note on Travel-Friendly Jackets for Petite Women}

In my opinion, White House Black Market does the BEST job on stylish jackets for petite women – whether for work, play, cold weather or just as a fashion accessory. They’ve really nailed feminine looks that fit petite women, and that will not go out of style.

They’re a bit expensive. One jacket is usually at least $150 but I find these are investment pieces as they will never go out of style and are (usually) good quality. Alternatively they do a lot of sales and good sales too – like as much as 40%-50% off.  So if you can wait, it can be worthwhile. Of course, you risk that the item or your size is no longer available.

{Quality and Longevity of Your Clothes}

I find the clothes at Macy’s to be pretty good quality and within what you’d expect for what you’re paying.

Keeping your clothes looking fresh is like karma – put care into it and you’ll reap the rewards. I think I’m super particular about this (and my fellow petite ladies can probably relate) that hitting the trifecta is kinda hard:

  • attractive
  • fits great without requiring alterations
  • within your budget

It’s particularly challenging for petite women because there are fewer options to select from!

I hope this article has been helpful! If it has please write in the comments and share photos from your dress-travel-adventures!

Cheers and happy travels!


Me, on the roof top of Marina Bay Sands, Singapore

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