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7 Shoe Styles That Make Summer-to-Fall Dressing Effortless

What shoes do you reach for when summer is ending, but you are not quite ready for full fall dressing? I always find this part of the season a little tricky. Sandals still feel right on warm days, but boots and closed-toe shoes start looking more appealing as the weather gets cooler.

The good thing is that you do not have to change your whole wardrobe at once. The right shoes can make summer dresses, skirts, jeans, and light layers work well into fall. I like styles that feel easy enough for warmer days but still have that slightly richer, more autumn ready look.

I found different options from American Rag Cie’s women’s shoe collection that fit this idea. From simple flats to tall boots and statement heels, these are the shoes I would keep reaching for as the seasons change.

1. 1460 Patchwork

1460 Patchwork
American Rag Cie
$200

If you want a boot with plenty of personality, this is an easy pick. This Dr. Martens classic has a rounded toe, yellow stitching, and a chunky treaded sole. What makes it special is the mix of hairy suede, leather, wild grain, and milled nubuck that gives the patchwork design a unique look.

I would wear these with a simple summer dress when the weather starts to cool down. They also look great with straight-leg jeans and a lightweight sweater. The chunky shape adds a little edge to even the simplest outfit.

2. The Abby

The Abby
American Rag Cie
$395

The Abby is the kind of boot that can make a simple outfit feel more stylish. This tall Tecovas boot has Western-inspired stitching, a 2-inch heel, and a soft leather lining. It is made from cowhide leather and has a leather sole, giving it a classic look that can easily work through the changing seasons.

I would pair these boots with a flowy midi or maxi dress while the weather is still warm. When fall arrives, they would look just as good with jeans, a knit top, or a light jacket. The sagebrush color is also a nice change from the usual black and brown boots.

3. Campus 14L

Campus 14L
American Rag Cie
$498

For a more relaxed Western feel, the Campus 14L from Frye is worth a look. It is made from scrunch leather and has a chunky toe, stacked heel, 13-inch shaft, and leather lining and outsole. The banana shade gives the boot a fun look without making it hard to style.

I would pair these with a denim skirt while it is still warm, then switch to jeans and a sweater as fall gets closer. They also work well with a loose maxi dress for a casual outfit with a little vintage feel.

4. Wyn Boot

Wyn Boot
American Rag Cie
$550

Looking for a boot that feels a little more special? The Wyn Boot is a lovely choice for dressier outfits. It has a rich chocolate-brown finish, a pale pink leather lining, a 5 cm heel, and a 7-inch shaft. The inside zipper makes it easy to put on, while the memory foam cushioning adds extra comfort. 

I would choose these boots for dinners, special events, or days when I want my outfit to look more put together. They would look especially nice with a simple dress or dark denim. The rich chocolate color also makes them easy to wear with many fall outfits.

5. Leone

Leone
American Rag Cie
$541

The Leone is a simple black ankle boot that you can wear with almost anything. It has a back zipper, a short heel, and a leather sole. The soft kid leather also gives it a comfortable feel while keeping the design clean and classic.

This would be one of my everyday picks because black ankle boots are so easy to style. I would wear them with cropped jeans and a light cardigan, or pair them with a skirt and tights when the weather gets cooler. They are simple enough for everyday wear but still look polished.

6. Mason Split Toe Ballet Flat

Mason Split Toe Ballet Flat
American Rag Cie
$125

Not every summer-to-fall shoe needs to be a boot. The Mason Split Toe Ballet Flat is a nice option for those warmer early-fall days. This black Matisse flat has a slip-on design, leather upper, round split toe, lightly padded footbed, and synthetic sole.

I would wear these with wide-leg pants, jeans, or a simple midi skirt. They give you a closed-toe option without feeling too heavy, making them especially useful during that in-between weather.

7. Sally Maryjane

Sally Maryjane
American Rag Cie
$450

For something more feminine and eye-catching, the Sally Maryjane is a fun choice. This Gini & Albert style has lustrous midnight-black leather, a sculptural metallic croc-embossed block heel, and a single strap across the foot. Memory foam cushioning and pale pink kid leather lining add comfort.

I would style these with a dress for a dinner date or a skirt and fitted top for a dressier daytime look. They also bring a nice statement touch to a simple pair of trousers.

The Shoes I’ll Keep Wearing

The best thing about summer-to-fall dressing is that you do not need to start over with your wardrobe. A few well-chosen shoes can make your favorite warm-weather pieces work for several more weeks.
With so many different styles to choose from, it is easy to find a pair that fits your everyday outfits. If I had to pick the most versatile options, I would start with an ankle boot and a ballet flat. They are easy to wear now and will still look great once fall is fully here.

RAED MORE: The Stylish Ankle Boots That Turn Simple Fits Into a Whole Look 

Bianca Todd

Bianca Todd

Bianca Todd shares fresh takes on fashion trends, outfit inspo and style tips that make dressing up feel fun, confident and uniquely you, only on TheDailyEdits.

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