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So You Want To Dress for Fall

Welcome back to “So You Want To…” the series wherein I give you outfits and *~*lewks~*~ for things like: time of year, a random event, a vibe, an energy!

This month we are diving back into regular ol fashion writing, and getting prepped for the greatest season, Fall!* While I might be adjacent to a fashion expert, I am absolutely a fall expert. I grew up in the Hudson Valley and thus I have reclaimed the right to act incredibly basic about fall, as my teenage years were spent selling pumpkins and apples to what we referred to as “the city people.” For years, I resisted the glee that driving down a mountain road on the first day the leaves change evoked, but no more! Let’s get wrapped up in a cozy sweater and munch on an apple (no Red Delicious, please) because we are talking Fall Fashion, baby!

Now, I don’t particularly believe in following trends per se — my general fashion ethos is if you know what makes you feel good, you should wear that thing. Still, I do think it’s helpful to be aware of what kind of trends are out there, if only so you are not perplexed at the offerings available to you. Plus, it can be fun to take note of a trend and mix into your wardrobe in a way that works for your style! I’ve gathered a combination of basic pieces that any fall wardrobe would need and some things that are more trend forward. As always, I encourage you to take what you like, and leave the rest! That might mean a color from one item, a print from another. At the end of the day, fashion is about what makes you feel like you!

*When I say “Fall” — I do mean East Coast Fall, I am biased and I apologize, I just have no idea how those on the West Coast do it, tbh.

Outerwear

A masc person in a blue bomber jacket, a femme in a red leather jacket, a femme in a long trench coat in a flannel pattern, a femme in a black-and-white checkerboard coat

Left to Right: Melton Bomber Jacket, BooHooman ($43.20) // Faux Leather Moto Jacket, Eloquii ($149.95) // Plaid Shacket Coat, Eloquii ($169.95) // Checkerboard Coat, Eloquii ($184.95)

As a woman who has been known to describe herself as a “coatsexual,” it was incredibly challenging for me to not select upwards of twenty coats and jackets here.

Consider, if you will, the classic varsity jacket. You can pair it with anything! You can femme it up (with say, a school girl skirt and platform boot?) or you can can butch it up (relaxed fit jeans and a white tee?), it’s casual and stylish, I love it. Next, we all know the moto jacket is never going to go out of style, not if we gays have anything to say about it. And since you likely already have a black one, why not try a faux leather in a bold color this year? Bright, saturated colors are happening in a big way right now, and this could be the perfect way to try out! Pair it with all black everything if it feels a little too bold, or toss it over the tan jumpsuit I’ve got down below.

For our next coat-testant, you might be saying “wow, plaid in the fall? How original.” And to that I say, you know, fair enough, but this classic happens every season for a reason! It’s giving academia, it’s giving English countryside, it’s giving effortless and chic. Over a cuffed jean and some Docs? Simply gorgina. Our final jacket is another opportunity to lean into one of the trends I saw all over the place researching for this, statement prints! You could even slide a bright turtleneck underneath and really go for it, if you dare. Or let the checkerboard do the talking, the choice is yours!

Pants

A femme in purple pleated wide leg pants, a femme in high waited baggy jeans in a dark wash, a pair of high rise jeans with holes at the knees, a femme in biker shorts with a white stripe down the sides

Left to Right: Pleated Palazzo Pant, Eloquii ($99.95) // Carrie High Rise Wide Leg Jeans, Universal Standard ($118) // High Rise Distressed Baggy Jeans, Target ($25) // Colorblock Bike Short, Eloquii ($39.95)

This season, the bottoms are going to be big and dramatic. (Same.) I would not be doing my due diligence as your gay fashion reporter if I did not report that I did notice a whisper of low rise jeans scattered about, but I was literally not strong enough to make myself include it here. I was a teenager in 2002, I cannot do it again. I hope you will forgive me

Thankfully, the shape that is really popular is an easy, relaxed fit, like the one in those incredible palazzo pants. I love a pair of pants like this because they look like you are doing a thing, but you feel like you are in sweats. Ideal! Additionally, I firmly believe everyone needs at least one dark wash and one black pair of jeans, thus I have provided you with these two options. And I had to include my personal fall staple, the bike short. I love the feint in the direction of athleticism on this pair, simply toss on an old hoodie and live out your Princess Diana fantasies!

Dresses and Jumpsuits

A collage of four people: a femme in a peach sweatsuit dress, a femme in a brightly patterned suit, a femme in a stripped dress, and a femme in a gender neutral taupe jumpsuit

Left to Right: Betterterry Hoodie Sweatshirt Dress, Madewell ($98) // Wide Leg Square Neck Jumpsuit, Eloquii ($139.95) // A-Line Dress With Puff Sleeves, Eloquii ($99.95) // Kate Stretch Cotton Twill Jumpsuit, Universal Standard ($185)

Neutrals are always in for fall, and this year is no exception. Muted pinks, olive greens, rusty oranges and tans are the ones that leapt out to me as I was rounding up items for this piece. If you aren’t ready for a return to any kind of “hard clothing,” you should one hundred percent slip into this hoodie dress. Honestly, add a platform or heeled boot and blazer to this and it’s suddenly dressy in a very cool, blase way.

Now, how about some fun prints? Florals, despite what you may have heard, are not just for spring! Fold in some darker ones, like on this very hot square necked jumpsuit and let me tell you, you will be turning heads in a big way. I also noticed an uptick in stripes, especially pieces that incorporate vertical and horizontal ones, as you see on the A-line dress from above. Also, note those bell sleeves and remember wayyyy back in the month when I talked about the 70s resurgence? It is still happening!

Finally, you cannot go wrong with a neutral jumpsuit in a slightly thicker fabric for the cooler months, you can dress it up, you can dress it down, you can go everywhere or nowhere in it!

Sweaters

A femme in a cream Henley shirt-style sweater, a close up of a sweater with a pattern of a cow on a farm at sunset, a close up of a sweater vest that is pink with multi-colored daisies, a femme in a black turtleneck.

Left to Right: Striped Bowden Henley Sweater, Madewell *Editor’s Note — this item is no longer available, here is a similar item MWL Betterterry Henley, Madewell ($68) // Aelfric Eden Sweater, Amazon ($25.99) // Daisy Gender Inclusive Sweater Vest, Nordstrom ($45) // Renee Raglan Turtleneck, Universal Standard ($88)

Put your hands together for the glorious return of the sweater! Perhaps it is just the fact that I am deeply into dressing like a field hockey coach these days, but I am loving this preppy Dad sweater from Madewell. And speaking of Dads, one of the best and most amusing trends I clocked in my research was that so many of the sweaters had the energy of like… Neil from The Santa Claus?  See also this sweater vest that has the same energy signature? It’s very gay and I very much like it. For a must have basic, get yourself a black turtleneck, I promise you won’t regret it.

Shoes

A close up of pair of Doc Martens, a close up of a loafer with thick cream soles, a Chelsea boot, a cream colored Rebook sneaker

Left to Right: DR. MARTENS 1460 Boot, Nordstrom ($150) // Emme Lace-Up Shoe, Nordstrom Rack ($39.97) // Newburg Leather Ankle Booties, Bluefly ($118.99) // Reebok Women’s Club C Sneaker, Amazon ($75)

Perhaps because we’ve got so much happening everywhere else — print and texture and fabrics, oh my — I purposefully went lowkey for the shoes. Here are some fall time classics, with a few updates. First of all, it’s fall, we’re all gay, here is a classic pair of Docs. What more is there to say? Next, a slightly dressy slide with a decent platform, because I am telling you now you will not be able to outrun the platform trend. It’s here to stay! For the Mommis out there, I am including this perfect Chelsea boot, one with a more slimmed down silhouette from the heavier styles of previous years. For a sneaker option, try a classic Reebok like this one, it’s retro, comfortable and will pair beautifully with your Princess Diana cosplay!

Until next month, my loves!!

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Christina Tucker is writer and podcaster living in Philadelphia. Find her on Twitter or Instagram!

Christina has written 118 articles for us.

14 Comments

  1. Omg that second jumpsuit so cute!

    I have a fashion question. Is that allowed? I like this whole dark academia vibe thing, despite it’s inherent issues, but I don’t want to dress like someone who wants to reanimate Margaret Tatcher. Any tips on how to look at home in a library but also kinda queer?

    (I usually dress femme. Plenty of skirts and dresses. Can’t stand to wear turtlenecks. Love wool. About EU size 44. Kinda muscular. On the edge of plus size here.)

    Thanks for anyone who has any tips :)

    • Yes! I think the most helpful thing to avoid that Disney channel energy is to minimize textures when layering! Think about the sparkly scarves, the weirdly textured sweaters, that weird sheer fabric that was everywhere circa 2006. If you wanna toss on a textured blazer or cardigan, don’t let the rest of your fabrics compete with that!

      Also, if you are doing say, a big dramatic cardigan, let that be the focal point! keep the rest of your look more form fitting—slightly cropped tee and maybe a straight leg or relaxed jean or pant. That way you’ll still feel like a grown up!

    • Personally I almost only find them in the “mens” department. Which is not always the fit I’m looking for. For a lot of pants making the pocket bigger or adding one is pretty easy, especially if there is a side seam.
      If you are crafty you can diy (Bernadette Banner has a tutorial on YouTube) or you can ask your local tailor.

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