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How to Dress for a Warm Fall

The heat just won’t quit, and it’s almost Labor Day! Usually, around this time of year, I would start transitioning my closet from summer clothes to fall apparel. Fall is similar to spring in that it starts very differently than how it ends. On day one, it feels like the height of summer, and by the end of it, it’ll feel so cold you’ll already be unpacking your winter coats. However, this year, the chillier fall weather seems such a long way off that I’m wondering if I’ll see any of my beloved knits and boots before Halloween. Instead of a transitional season between summer and fall, summer just seems to be extending longer each year. By this point, I’m experiencing some major outfit fatigue with my warm-weather wardrobe. Of course, it’s just not practical to unearth autumn appropriate clothing, so how do you dress for a warm fall?

Start by embracing your favorite pieces from summer. Yes, you may be tired of wearing the same cutoffs shorts day in and day out. So, switch things up with pieces you haven’t worn as much these past grueling months. Give shorts a rest and try dresses or skirts. When dressing for hot weather at any time of year, the key thing to remember is that layers are your best friend. Fabrics and styles that give you that cozy fall feeling—knits, turtlenecks, blazers, trousers—all have cooler alternatives.

Speaking of alternatives, sweater weather may be quite some time off, but you don’t have to forgo wearing knits. Boxier, looser weaved tanks are the turtlenecks of late August. You can wear them solo now, then incorporate them as a layering piece when the temperatures start to dip. If you’re sick of wearing the same style t-shirt, switch things up with a muscle tee. Keep it classy with a padded shoulder version, which is available across price points from Forever 21 up to top designer brands. If you are going with long-sleeved shirts, they should be airy and made of cotton to help keep your body temp low.

From tops to bottoms, I don’t think many people have given their skinny jeans a second look since the pandemic started, and the good news is that you still don’t have to. Sweating in a tight pair of jeans is not ideal, so opt for baggy denim, like boyfriend jeans and loose-fitting trousers. Linen drawstring pants are a great summer-to-fall transition piece, as are palazzo pants and culottes. Again, you want to look for these silhouettes in breathable fabrics and don’t be afraid to pick up a pair in a fun novelty pattern or bold color. A bright red cropped flare-legged pant will look just as good now as it will in the holiday season.

For dresses, versatility is the ticket. When you’re considering a new dress to see you through to fall, opt for one that will look good with tights. Not all warm-weather frocks can transition into a cooler season, and you’ll want something that will carry into fall when the mercury starts to drop. For my money, oversized midi dresses are the way to go in a never-ending summer. Try a baggy (but not sloppy) simple t-shirt style dress for a minimalist late summer style, and then pair with leggings and a denim jacket come October.

Speaking of the denim jacket, even in the warmer-than-normal fall, outwear does have its role to play. Eventually, the evenings will get chillier, and you don’t want to be caught outside bare-shouldered and goosebumped. Go with lightweight styles like linen blazers, utility jackets, and of course, the aforementioned denim jacket in a boxy cut. For a sporty look, go with a windbreaker or warm-up hooded style in a bold graphic print. Of course, you can also consider stowing an oversized scarf in your day bag to wrap-up in once the sunsets. Just make sure it’s not too heavy like pashmina, but airier.

Lastly, footwear. My poor feet are pretty much done with sandals and flipflops; they need a break. So, I’m looking at chunkier shoes for the next few weeks, that will also serve me when pumpkin spice lattes are up for grabs. (I know that they may already be available, but I just can’t stomach the thought until we hit daily highs in the 50s). I particularly like an oxford loafer to wear now with barely-there-socks, and then bust out my argyle knee-socks later on. Another great style show for this transitional season are white sneakers, from brands like New Balance and Reebok, these functional shoes are also great for a low key, yet still, pulled-together look.

Fall will eventually come our way, and we can either wait it out wearing the same old tired tank tops and cutoffs or try to up our transitional style with a few key pieces to see us through. Just remember to opt for items that not only look great now but will also serve you when the leaves start to turn.

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