The Well-Dressed Tomboy’s Guide to Fall Fashion


Fall is a time to celebrate new beginnings, the changing of seasons, the proliferation of the color orange, and, of course, the unleashing of fall fashion. As a masculine of center dresser, your average tomboy launches into the autumn of the year with a wardrobe bursting with plaid, denim, leather jackets and beloved hiking boots.

While there’s nothing wrong with that, some who aspire to a more refined and professional aesthetic may find themselves wondering how to upgrade their look while still staying true to their personal style. We’ve got some tips and tricks for putting your best foot forward this fall!


The Secrets of Layering Clothing

Everybody knows the best thing about fall fashion is that you get to bring out the wardrobe items that are normally too toasty for summer. Yes, it’s time for the wonderful season of layering! Although you may not know it, there’s a science and an art to layering. Let’s walk through the fundamentals.

First, remember to layer from thinnest to thickest, material wise. This is for a reason: as you’re going in and out of environments that fluctuate in temperature – and indeed, the great outdoors itself has a habit of fluctuating in temperature throughout the day during the autumn – you want an easy way to go from sweltering to comfortable. If you’ve got a super thick and warm shirt on underneath of three thinner layers, it takes a lot more awkward wrangling to get rid of the guilty party when you start to realize you’re over-insulated. This stacking of thin-to-thick has another purpose, too: it makes the shape of your silhouette less chunky and more deliberately dimensional, with an architectural outline that looks right and moves nicely.

Aesthetically, there’s another element to consider when strategizing the order of your layered garments: color and pattern. A good rule to follow is that you should go from the most subtle to the least subtle, either inside out or outside in. So, for example, you could go from a plain white shirt, to a solid blue vest, to a checked patterned jacket. Alternately, you could go from a bright orange and black polkadotted shirt, to a black v-neck sweater, to a muted charcoal jacket. (If you own this outfit, please send us pictures.)

Finally, when planning your layered outfits, you need to make sure that each visible item can stand on its own merits. The advantage of layers is that they can be easily removed to suit the weather – which means you need to be prepared to look sharp and classy at each stage of layer removal. You don’t want to be stuck sweating in three layers too many because there’s a hidden mustard stain underneath your argyle sweater vest, or an embarrassing logo from a cartoon you liked as a teenager on your t-shirt.


If You Wear Plaid, Wear It Stylishly

Yes, it is possible to wear plaid and still look stylish instead of sloppy. We all love to be comfortable, and plaid is a guilty pleasure for many people all year round and not just during the fall. So how do you indulge in a love of that classic pattern without making a mess of your carefully curated aesthetic? Here are the two key things to remember: fit and pairing.

The fit of a plaid shirt is what makes or breaks the essential classiness of your look. A well-tailored shirt brings out the best in everyone, so if you find that magical garment that looks like a chesterfield from the 70s but fills your soul with inexplicable joy, go ahead and buy it, but then take it to a trusted tailor and get it fitted to your unique silhouette. This doesn’t have to mean tight or uncomfortable – it’s just taking into consideration that all off-the-rack clothing can be improved to better suit you, because each body is a unique shape and size. Super loose and baggy is a look, but it’s not always a look that commands respect. If you want to rock the plaid and demand the attention and admiration of the people around you, you want a custom-tailored shape that shows off your taste in a way that makes it look like you’ve mastered the plaid, instead of the plaid mastering you.

Now, all that said, you can elevate any garment by what you choose to pair it with. Your plaid shirt, custom tailored, will look nice enough, but will still have a casual vibe not appropriate for the office if you’re wearing it with sneakers, a hoodie, and jeans. On the other hand, you can bring your fashion to a sharp and dapper point by matching your upscale lumberjack look with some nice chinos, a pair of dress shoes or formal boots, and a suit jacket. Bonus points if you add a classy necktie in a simple, solid color like black or navy blue. Obviously, this will be easier to do if the plaid is a thinner fabric instead of a thick, genuine flannel – be sensible with what you’re working with and don’t put a silk tie on a flannel shirt dense enough to be pajamas.

Finally, if you truly are a plaid aficionado, you should consider other ways of including that iconic pattern in your fall outfits. Plaid accessories, like socks, ties, scarves, and even watch bands can bring that fall flair to your outfit without forcing you to compromise on formality or office appropriateness.

Doreen Pierre shot by Charley Malone for Autostraddle

Choose a Nice Pair of Dress Boots

When the weather starts to get colder, there’s a familiar satisfaction to be found in the feeling of pulling on a nice pair of ankle-high boots. To face the chill with flair and style, it’s important to expand beyond the classic hiking boot or slip-on chukka, neither of which should really be worn to the office or to a formal occasion. Dress boots send a message of strength and adaptability, but also one of professionalism and panache. The perfect dress boots, when worn with a long pant leg, are easily mistaken at a glance for a quality pair of dress shoes. Nobody would ever see a pair of muddy hiking boots peeking out from under some single pleat midnight blue tuxedo pants and think they belonged together. Don’t trap yourself into having to decide between warm feet and appropriately dressed feet. Dress boots are the answer: versatile enough to be worn anywhere dress shoes go, but also appropriate for weekend adventures in the city or a low-key date night to that local craft beer place you’ve heard good things about.

Remember, when the weather is cold and rainy, you need to take extra good care of your footwear. You should be using shoe polish or cream to gently clean, shine, moisturize and waterproof your boots, whether they’re genuine leather or vegan leather, on a regular basis. Depending on how often you wear them, the weather conditions you wear them in, and how you store them, you should be doing this every eight weeks at the absolute minimum. If you’ve worn your boots out in the rain or muck, wipe them down and don’t leave them sitting with the moisture on them. You’ll also get more longevity out of them if they aren’t stored in direct sunlight, but the most important thing is remembering that when you’re wearing them a lot in rough weather you’ll want to up that frequency of care to as much as every two weeks.

To go along with your boots, you’ll want to invest in some nice wool socks. Dress boots are typically thinner material than other boots and will benefit from the insulation if you do need to navigate a blustery day. Additionally, when you wear the boots with a shorter leg – and yes, come spring time you’ll absolutely want to wear these boots out with your favorite capris – a nice pair of wool socks with interesting but understated texture and color will emphasize your excellent fashion sense.

Here at Tomboy Toes we believe tomboy fashion should be empowering and joyful instead of confusing and stressful. Ready to arm yourself with more dapper dressing knowledge? Check out our guide to dressing better as a masculine-of-center fashion lover and our list of top five dapper dressing mistakes.

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