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Fall Finds & Outfit Planning

I find with most things in life, it’s best to be prepared. But, for reasons seemingly beyond my control, I’m always shocked by how quickly the next to-do item, activity, event, project, season, or school year looms before me. With Labor Day fast approaching and autumn about to make itself known, I’ve finally started my fall list of garments and accessories from which I’ll base my seasonal wardrobe. From cozy sweater dresses to neutral layers and chic boots, here are the fall finds and strategies for outfit planning in the coming cooler months.

When taking stock of your wardrobe, you will probably already have some tried-and-true staples, like turtlenecks, jeans, button-down shirts, and sweaters. In fact, like me, you may have a variety of these go-to pieces, which can be overwhelming. Instead of outfit planning around every last garment you could wear this season, select four or five of your top options. These should be picks you’re most likely to wear that need little-to-no maintenance to be outfit-ready and have styling versatility for multiple looks.

Next, make your shopping list for fall finds that you’re lacking. This list can consist of basics as well as statement pieces and should include accessories, footwear, and outerwear. My list this season features baggy jeans, heeled loafers, a workplace bag, and anything plaid.

Garments that are trendy for Fall 2023 that you may want to consider adding to your closet include Ballet flats, midi denim skirts, half-zip sweaters, flare-legged jeans, and boucle blazers.

If you want to fill in your transitional clothing options for chilly mornings that turn into sweltering afternoons, look to sleeveless turtleneck tops, lightweight cardigans, trouser shorts, and wrap dresses. These all work as layered looks for fluctuating daily highs and lows.

Once you have your list of finds, it’s time to shop — or, more so, research before shopping.

Nowadays, there are very few and far between one-stop shopping destinations. Sure, you’ve got your Macy’s, Kohl’s, and Nordstroms, but even these department stores can fall short on every item on your list and within your budget.

Oh, I forgot budget. Yeah, make one. If not a full budget, then a maximum price you’re willing to pay for any particular garment. Keeping budget in mind, research which stores and sites offer you what you’re looking for at a price you can afford. You may already have your go-to brands for particular items, so start there, but don’t be afraid to shop around.

Speaking of shopping around, don’t limit yourself to traditional retailers. For my baggy jeans search, I’m looking at secondhand and thrift shops. And I’m not just browsing the women’s section. I’ll also be exploring men’s denim for the perfect slouchy, worn-in look. A trick with oversized pieces, especially thrifted finds, is customizing the fit with alterations if you’re handy in that way, or for a no-sew option, there are adjustable button pins for jeans that will allow you to realign pants buttons. On the opposite end, you could also utilize a button extender. Raising or lowering hems, taking seams in, or replacing zippers and snaps are other ways to customize and revitalize secondhand purchases. And don’t feel limited to in-person thrifting. There is Poshmark, Depop, and ThredUp for online thrift shopping.

Another shopping alternative to consider is subscription or styling services. Companies like Stitch Fix, Wantable, Gwynnie Bean, or ThreadBeast all offer curated boxes sent to your door to try on and outright purchase or rent-to-purchase. Working with a stylist can take out a lot of the leg work, literally, of searching for items and figuring out sizing.

Once you have a roster of pieces, you can start outfit planning. This can be as detailed and specific as you want or a general loose idea of outfit building blocks. You can schedule certain looks for certain days or identify key items you want to wear each week. It’s whatever works best for you, your daily needs, and, of course, the weather.

I like to categorize my outfits based around my weekly activities. There are work-from-the-office outfits on which I spend the most effort and budget. There are work-from-home looks that also double as errand-running and hiking looks. Then, there are weekend outfits divided amongst family activities, going out, and church ensembles. There can be some crossover; I may wear the same dress and cardigan on a Sunday that I do on a Wednesday, and I may don the same athletic leggings for a walk in the woods that I do for family mini-golf. The main point of outfitting planning is not to stress it but to be prepared for the week(s) ahead and hopefully look and feel stylish in the process.

Lastly, don’t forget the final touches. We all need a bottom, top, shoes, and a jacket for fall, but an outfit calls for a bit more. Jewelry, hair accessories, belts, hats, scarves, a bag, and cosmetics all contribute to an overall look. You don’t need a whole cadre of accessories for each look; just having standard quality pieces that elevate any outfit is the simple trick to accessories. I rotate three watches, two sets of rings, and four different necklaces with all of my outfits. So, while the accessories are repeated often during the week, their pairing with different outfits still gives polish to the overall looks.

There is no one right way to shop, style, or outfit plan. It’s all about what works best for you, whether you lay out each piece of your look the night before or only have a general idea of what to wear on the day. The key idea is to be prepared as fall approaches, which will hopefully take away some of the stress with sartorial decision-making in the season ahead.