Petite Friendly Fall Skirts and Dresses

For anyone 5’3″ and under, finding the perfect flattering length in skirts and dresses can be quite a chore. Skirts and dresses are great not only in summer, but for fall as well, particularly midi skirts and dresses. They are so pretty paired with ankle boots or tall boots and jackets.

Skirts and dresses in fall colors and prints are also a great way for those in warmer climates to still have fall vibes. I refused to be left out of the look so I’ve been scouring the retailers for petite friendly fall skirts and dresses.

My favorite easy to order and to return site came through with a few pieces. Finding petite friendly skirts and dresses from Amazon isn’t always easy, but at least the shipping and returns are low hassel and free ( with a Prime account) since you have to go through a few misses to find the hits.

Skirts and dresses are rarely labeled petite at Amazon but measurements are usually given so it helps to know your measurement- the length of skirts and dresses that hit at your sweet spot.

I’ve styled these skirts and dresses with Thanksgiving outfits in mind but they are perfect for all your fall gatherings and events. Skirts and dresses are especially nice for Thanksgiving because you can dress up a bit and still eat to your heart’s desire without having a constricting waistband. Go for elastic or stretch waistbands in skirts.

Note: I’m wearing a medium in most of the skirts and dresses, and small in the tops.

Petite Friendly Fall Midi Skirts

Lavender is a trending color this fall. When lavendar is placed on a dark background like black, it makes the perfect fall floral print. This floral print skirt is a tiered aline skirt with an elastic waist. Aline skirts are generally universally flatteting to all body types and also a good choice for petites, especially petite pear shapes. An aline is a good starting point when looking for petite friendly fall skirts and dresses.

While black boots would be a good choice for taller ladies and would coordinate well with this skirt, I chose a camel color ankle boot to extend the leg line and create a little more height. The top is a waffle weave so it’s more casual but works with the skirt to create a dressy casual outfit perfect for Thanksgiving dinner.

fall skirt outfit with lavender top

Skirt- Amazon; top- Amazon; boots- Amazon; necklace- similar; earrings- Kendra Scott

The rich earthy brown color in this floral skirt screams fall. Paired with this pretty embroidered top in rich fall colors, it would be perfect as a Thanksgiving Day outfit, or for wearing to a fall bridal or baby shower.

This skirt features a ruffle hem and side zipper with elastic in the back half of the waistband. It’s also high waisted and almost too high for me, but still manageable.

Petite friendly fall skirt with embroidered top

Skirt– Amazon; top- Amazon; boots- Amazon

I featured both of these pieces styled with other pieces in my Cute Thanksgiving Outfits post.

This skirt is from Old Navy and comes in a petite. It doesn’t appear to be currently available in petite but it might get restocked. This one is similar and is available in petite. The fun orange color is easier to style than you might think. Wear it with grey or olive, in addition to cream or white.

I paired it with an ivory lace trimmed cami and a cognac suede moto jacket, but this fall midi skirt can be dressed down too.

petite orange floral midi skirt outfit

Skirt – Old Navy; cami- similar; jacket- Nordstrom; similar boots- Amazon

Petite Friendly Fall Dresses

Finding petite friendly dresses can be daunting. My lack of height comes mostly from my upper body and short torso, and not my legs, so buying a mini skirt or mini dress isn’t the answer. The skirt or dress is often still too short in spite of my overall height of 5’2″. Midi dresses tend to make me look frumpy because they fall too long on me.

Here are a few petite friendly fall dresses of different lengths that work if you are in a similar situation as me. Wear these for your Thanksgiving outfits and you’ll still look polished and be comfortable no matter how much you eat.

This cute little floral dress is fully lined and has a hem that dips a little lower in the back. The front falls at knee length on me, which is my most favored length (in spite of it being labeled a mini dress, this one wasn’t too short.) Add a jacket for warmth. Add tights as well if you are in a really cold climate.

Jacket- Nordstrom; dress- Amazon; boots- Amazon; necklace Kendra Scott Shop the look HERE

This dress features a wrap top and elastic waist. The material is smooth and silky feeling. The pretty dark floral print is perfect for fall and the dress looks great topped with a jacket. The cognac brown moto in faux suede gives it even more of a fall feel.

floral vneck midi dress
fall dress outfit with cognac moto

Dress- Amazon; Jacket- Nordstrom, similar; boots- old/ similar

The same dress as the red one above, because it’s so good you’ll want it in all the colors. I paired the blue one with a button front cardigan. This makes a cute outfit option for fall brunches, showers and for Thanksgiving day.

Floral blue mini dress with button front cardigan Thanksgiving fall outfit

Dress- Amazon; Cardigan- Amazon; boots- Amazon

This dark moody floral dress falls just below my knees. It could be just a little longer for wearing with tall boots but it does come just over my boots. It would be perfect for those who are shorter. It has an empire waist and three buttons on the top, but it doesn’t button. They are purely decorative.

This flowy dress would be comfortable for holiday gatherings and comes in several colors. The ruffle hem and sleeves make it more feminine. I’m wearing this one in a small.

fall midi dress for petites

Dress- Amazon; boots- Naturalizeroption; necklace- Amazon; earrings- Loft

Color makes a lot of difference. This is the same dress in light blue. If dark moody florals, aren’t your thing, this pale wintery blue would be perfect. This dress has a side front split, but it doesn’t seem to fall open much.

Midi dress for petites

If you are a sneakers and dress kind of girl, this dress is adorable with sneakers. The khaki and grey in the print pair perfectly with these light taupe faux suede sneakers from Old Navy.

how to wear sneakers with a dress

tote- Amazon

Add a button front sweater if you need more layers and warmth.

fall floral dress with button front sweater

Sweater- Target

Don’t discount a sweater dress for being cozy and comfortable. This color block sweater dress is the softest I’ve ever worn. I wore it a lot last winter while teleworking. I’m wearing a small, size up for a looser fit. It’s still available in some sizes and in other colors and solids.

sweater dress outfit

Dress- Amazon; boots- Nordstrom

I easily recommend any of these petite friendly fall skirts and dresses for Thanksgiving outfits and fall events. You can be comfortable and stylish. Many work for non petite/ regular height women as well.

petite friendly skirts and dresses