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How to dress yourself in Bend, Oregon

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A glimpse at Bend’s highs and lows for Wednesday, Sept. 26, 2018.

If you’re old enough to read travel blogs, you’re old enough to know how to tie your shoes and choose a shirt to match your pants.

But knowing how to dress yourself in Bend is a different matter, particularly in shoulder seasons like fall and spring. As September draws to a close, we’re seeing temps that range from the 30s in the morning up into the 80s in the afternoon (and back down again at night).

Suffice it to say, that’s tough to plan for. Here’s how to layer up Bend, Oregon style.

A couple caveats…

The following is NOT intended to be an all-encompassing primer on attire for your multi-day backcountry adventure (go here for a roundup of the ten essentials and here for some ideas on packing for your Bend vacation).

This is more about how to look cute while avoiding freezing your butt off or sweating like a snowman in a sauna.

I’ll also clarify that this will be more geared toward ladies since—um, well, I am one. And since our wardrobes tend to be more complex, but don’t worry, guys—most of these basic principles apply to any gender.

Blogger Tawna demonstrates how to layer up (or down) for shoulder season in Bend.

Now let’s talk layering.

Get up, get dressed!

Start your day by layering up. On your feet, you want some sturdy wool socks that can be rolled up and stuffed in your purse or pack later in the day. You’ll find lots of selections at FootZone, Pine Mountain Sports, or Columbia Sportswear at the Bend Factory Outlets on the south end of town.

Your footwear can be anything from hiking boots to dressier boots to sneakers or slip-on hikers. I’m a big fan of the latter, particularly the ones made by Merrell, which you can find at FootZone, cc McKenzie, and Shoe Inn, among other places. Some folks even go for the socks-and-sandals look (it’s Oregon) or keep a pair of flip-flops stashed in a purse (raises hand).

Jeans are a safe bet for the bottom layer, or opt for some cute convertible pants that roll into capris (North Face, Columbia, Merrell, Prana—tons of brands make them, and you’ll find most of them at REI in the Old Mill District).

Next up, your torso. I’ll leave the bra thing to you, but you want to top that with a tank or T-shirt to add a layer of warmth. Bonus if it’s something you feel okay wearing solo when temps spike into the 80s. Next, pull on a longer-sleeved shirt (I dig elbow-length sleeves this time of year) and top that with a cute flannel or light fleece.

A puffy jacket, light gloves, and an ear warmer or cap will complete your ensemble, and now you’re ready for anything from a brisk morning hike to brunch at one of the outdoor fire pits at McKay Cottage. Go, you!

Gents, you’ll follow most of the same principals. My husband’s a big fan of zip-off cargo pants that convert to shorts later in the day. A dri-fit T-shirt topped with a couple longer-sleeved layers and a warm jacket gives you a variety of layers to peel off (and put back on) as temperatures warm and cool.

No matter your gender, you’re smart to carry a purse or day pack that gives you a spot to tuck your discarded layers or access them quickly as needed.

Now start stripping!

As the day warms up, you’ll start losing layers.

My feet overheat first, so here’s where I’ll ditch the wool socks and wear my Merrell slip-ons solo, or stuff the boots in my car and switch to sandals.

Next, cuff those jeans or zip off the legs of your convertible pants. Ahhh…sunshine!

Slip-on hikers like these ones from Merrell do double-duty with wool socks for warmth or sockless with cuffed jeans, capris, or shorts.

This is where you’ll start to appreciate the order in which you’ve layered your midsection. You can peel off a jacket, then fleece or flannel, then long-sleeved tee as the day wears on without having to hunker down in your backseat and undress like a creeper.

Your unsexy strip show will typically progress between the hours of 10 a.m. and 6 p.m., at which point you’ll notice a chill in the air…

Put it all back on, baby!

I’m guessing I don’t need to tell you how to get dressed again, so I’ll skip that level of instruction.

What I will tell you is that temps can drop dramatically as the sun starts to plummet, so make sure you’re prepared. That sunny little patio table where you’re enjoying your happy hour cocktail in short sleeves at 4:30 p.m. could morph into an icy-cold shiver zone by 6, so keep your layers close.

As the evening wears on, that’s when you’ll bust out the thicker jacket, gloves, and hat. Bend doesn’t see a lot of rain, since it’s the high desert. That said, it’s not a bad idea to have at least one water-resistant, wind-resistant layer handy.

Keep an eye out for restaurants, breweries, and hotels with fire pits, since those are some of the most delightful spots to enjoy a chilly fall evening. Some of my favorite fire pits along the Bend Ale Trail this time of year include McMenamins, Worthy Brewing, and either of the two 10 Barrel locations.

Now go out and get dressed. Or undressed. Whatever.



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