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Apple Picking Outfits: What to Wear

It is mid-October and decidedly fall here in Ohio. That may mean a few things to you-embracing the season by stocking up on Halloween décor, taking the opportunity to photograph the beautiful changing leaves, or updating your usual Starbucks order to a PSL.

One of my favorite ways to celebrate the season is by heading outside to the apple orchard or pumpkin patch for some freshly picked produce. Homemade apple pies? Roasted pumpkin seeds and jack-o-lantern carving? So nostalgic! In such uncertain and unprecedented times, carrying out traditions like these can feel therapeutic. Many of us have been doing these since we were kids. Plus, the activities are perfectly suited to social distancing while scratching our itch to get out of the house. It’s also the perfect excuse to change out of your sweatpants and into your best apple picking outfits.

Apple-picking season in Ohio runs roughly from late July to late October depending on the variety, and pumpkin season is at its peak throughout October. Take these final weeks to bring your kids, significant other, or best friend with you for these fun fall activities! If you’re heading to the pumpkin patch or orchard for a fall family photoshoot, sign up for an appointment here for a full styling session. Otherwise, keep reading for some outfit ideas.

If you are going to get out of the house, you might as well look good doing it. Something about all the time confined at home makes getting dressed for any outing feel like it takes a bit more effort. A little inspiration is definitely in order to put together your perfect apple-picking outfits. Look for fall prints and color palates, heavier fabrics and knits, and pieces that will keep you comfortable throughout the day. These 3 easy apple-picking outfit formulas will help to get you started.

Classic: Knit Sweater + Knee High Boots + Flat Brimmed Hat

Apple Picking Outfits

The first outfit formula starts with a sweater—an essential we should all have in our fall and winter rotation. You can choose a fine knit for a more refined and classic look or a heavier knit to get in on the chunky sweater trend going strong this season. Pair with your favorite denim and a pair of knee-high boots. Skinny jeans will work best with the taller boots to create a streamlined look and prevent bunching, especially if your boots are a slim riding boot or stretch style. For boots with a more relaxed fit through the calves, slim-straight cuts of denim could also work. Alternatively, a sweater dress would work just as well.

Knee-high boots can be intimidating to buy due to the inherent fit concerns: Notably, they are typically made of rigid leathers or suedes that won’t stretch to fit different calf sizes. Petite women may worry about the shaft height “cutting” their frame and making them look shorter, while taller women may worry that the shaft doesn’t come up high enough.

So, what should you consider when buying and styling them? The best advice is to measure, measure, measure. Women with curvier calves should measure their calves to ensure a comfortable fit and search for boots labeled as a wide calf. Tall women should measure the height of where they want boots to stop and compare to the boot dimensions. Women worried about looking short may consider boots with a small heel and should take care in styling their full outfit. For example, a black knee-high boot paired with a black jean will elongate the legs rather than cutting them in half.

Finish your apple-picking outfits with a classic fall accessory, the flat-brimmed hat, to pull it all together. I love this hat with a boot because it balances the overall proportion of the look by drawing attention upward. A shade of brown or beige keeps this accessory timeless.

Edgy: Suede moto jacket + Bodysuit + Distressed Jeans + Textured Ankle Boots

Apple Picking Outfits
We have discussed how perfect a moto jacket is for fall dressing in previous weeks, but if you’re still not convinced, allow me to mention it once more. I like a suede moto in apple-picking outfits because the texture tones down the edginess a notch and it’s a little easier to move in than a thick leather. Like most things in fall, earth tones will be your best bet to maximize versatility.

The boxier, structured fit of a moto jacket is an ideal match for something more figure-hugging underneath. A bodysuit does just that! I love the clean lines bodysuits provide in outfits because they always stay smooth and in place. A simple bodysuit is your best option. You do have choices in the shape, however. Turtleneck bodysuits are my go-to for elongating your body and providing a little extra warmth, but a V-neck or scoop neck works well for showing off necklaces. Choose what you feel most comfortable in. Match a camel-toned bodysuit to a similarly colored jacket for an easy play on monochromatic hues.

On the bottom, add a pair of distressed jeans. High-waisted denim will keep you tucked in and prevent you from feeling overexposed in the fitted bodysuit. Try slightly more rigid denim to contrast with the stretch of the bodysuit. Finally, slide on a pair of textured ankle boots, such as a snakeskin texture. This detail has been a huge trend for a few seasons now and is so versatile that it won’t feel outdated in years to come. Black-and-white or brown-and-white snakeskin prints are just as popular and easy to style as a simple embossed black boot. Other textures to keep on your radar are croc and calf hair, and there are vegan options for all of these!

Casual: Oversized Plaid + Cropped Thermal + Black Distressed Jeans + Converse


Our last outfit formula pays special attention to comfort. Start with a simple outfit base of black distressed jeans and a thermal. Black or white varieties will get worn time and time again. We’re going to pair this with an oversized plaid shirt, so to keep proportions balanced and not lose sight of your waistline, go for a cropped thermal. Cropped doesn’t have to mean exposed if you’re worried about skin showing or the cold temperatures – just meet the shirt hem with a high waisted jean to close the gap. A black pair will work well with the overall look to push the vibe slightly masculine and outdoorsy. Opt for a skinny, tapered, or slimmer straight leg to allow the oversized shape of the plaid to shine. Too much volume on the bottom risks being visually overwhelming.

For your plaid layer, you could choose a classic flannel button-down or go even heavier with an over shirt or shirt jacket style. These are often made of heavy wool, which will be more insulating as temperatures drop. Look for long lines on this layer. A hem, that hits anywhere from the bottom of your hip to mid-thigh is perfect! The plaid print is synonymous with fall style, and the oversized silhouette brings a fresh modern flair. Finish the look with a pair of Converse or similar basic canvas shoes. Try cuffing your jeans if paired with the high-top version. These sneakers will keep you comfortably on your feet for hours, making them the perfect practical choice for your apple picking outfits.

Wrap-Up

For most of us, there is no way we’re going apple-picking without snapping a few photos, and you’ll want your outfit to be attuned to the scene. Give these apple picking outfits a try for a casual and comfortable day in the outdoors that doesn’t skimp on style. They build on basics that you probably already have in your wardrobe and give them new life. Still missing a lot of the basic pieces? Check our Fall Wardrobe Essentials guide for must-have pieces that can be styled and restyled for all your fall outings. Enjoy the fall festivities and happy apple-picking!