The transition from late summer into early fall in Chicago is anything but predictable. One day can feel like the height of summer, while the next brings cool mornings, steady rain and the first real hint of colder weather ahead. That variability makes the Chicagoland area an ideal place to put outdoor gear through its paces.
The gear in this review was tested across a wide range of conditions, from woodland field work and urban commutes to complete downpours and hot, sunny days. For me, testing gear in the Midwest is a great litmus test for versatility—especially heading into fall, when what you wear and carry may need to handle several different conditions in a single day.
This review is broken into five sections: shells and weather protection, shirts and layers, footwear, packs and travel, and accessories. Whether you’re squeezing in the last warm-weather adventures of the year or gearing up for cooler fall days, these pieces offer plenty of versatility for the changing season.
Shells and Weather Protection
Paramo Velez Jacket
This jacket is truly exceptional. This piece was a go-to for me throughout the wet Chicago spring and its light insulation is perfect for when it is cooler. The Velez uses Paramo’s Nikwax Analogy waterproof system instead of a traditional membrane, which helps with moisture management during movement. Large vents and an active fit make it particularly suited to wet-weather hiking and intense exercise.
Filson Shelter Cloth Waxed Anorak
Built with waxed cotton calling back to a more traditional style, the Shelter Cloth Waxed Anorak emphasizes durability and weather resistance over lightweight efficiency. These jackets can get passed down for decades and their heft is great comfort to me. You don’t need to be precious with this jacket and the old-fashion waxed jacket has a style of its own that I love.
Stio Dawner Hooded Jacket
Built as a lightweight insulated layer for variable conditions, the Dawner Hooded Jacket bridges technical insulation and everyday wear. I love wearing this jacket at dawn! It is a perfectly appropriate name. This jacket has a low-bulk construction and is great for throwing in a weekender travel bag. The basic weather resistance of the jacket makes it a versatile piece for cool mornings and shoulder seasons.
Showers Pass Cloudburst Hoodie
Designed around breathability and mobility, the Cloudburst Hoodie combines lightweight waterproofing with stretch fabrics and ventilation features. The “it” factor for me is the stretch aspect of the hoodie which makes cycling and running comfortable. There is a wonderful balance of weather protection and active comfort with this piece. I also wore this jacket during a rafting trip through the Grand Canyon and it was a needed waterproof layer that really held up.
L.L.Bean Trail Model Rain Jacket
Built as a straightforward rain shell, the Trail Model Rain Jacket emphasizes packability, affordability and lightweight weather protection. The simplicity of this jacket makes it easy to throw in a pack for uncertain forecasts and travel days. I keep this one in my car for easy access if rain comes.
La Sportiva Discover Shell Jacket
The Discover Shell is designed for weather resistance and strong construction. This piece isn’t as mobility-friendly as some of the other jackets on this list, but it is very hearty. This jacket took hard days of field work, and with a quick rinse under a hose or sink, this jacket is back to new. This is a classic example of an exemplary shell.
Salomon Bonatti Waterproof
Built for fast movement, the Bonatti Waterproof emphasizes low weight and packability for runners and fast hikers. This minimalist approach focuses on providing weather protection without adding bulk. This jacket also comes in excellent colors like Marlin and Coffee Bean.
Fjallraven Keb Lätt Wind Jacket
On the lighter half of this category, the Fjallraven jacket is between a shell and a windbreaker. This jacket is built around breathability and packability and is the perfect “just in case” jacket. It is intended for changing conditions where wind resistance matters more than full waterproofing and this has proven to be a lifesaver on a few occasions.
Shirts and Layers
FarPointe Sun Cruiser
I wore this sun hoody for 6 days while in the Grand Canyon on a rafting trip and I was so glad I had it. It is light-weight and very breathable. It doesn’t stick to your skin and allows for great airflow throughout the hoodie. I would highly recommend this piece in hot dry environments like in Arizona.
Ibex GOAT Short Sleeve Crew
As highlighted in my last review, Ibex makes incredible Merino wool products. This is just another testament to the quality of the products. The GOAT Crew emphasizes temperature regulation and odor management, as wool is a naturally odor resistant fabric. I wear this one for everyday use, as well as intense technical hikes.
Ibex Nomad Henley
Again, Ibex at its best, except this piece is a little heavier weight and is conveniently cut to be a Henley-style shirt. This long-sleave blends casual aesthetics with performance-focused materials as well, sporting the benefits of Merino wool well. This piece is optimal for travel and folks moving frequently between urban and outdoor settings.
L.L.Bean Comfort Stretch Performance Shirt
This button-down takes stretch fabrics and casual styling and blends it together for travel-friendly comfort. LL Bean makes trusty pieces and this shirt is evident of that. This shirt has a casual looking approach, while retaining performance features in the fabric.
L.L.Bean Comfort Stretch Everywhere Chinos
Rooted in a similar mindset as the performance shirt, these chinos also aim to bridge technical apparel and everyday clothing through stretch materials. I appreciate the wide variety of color choices and sizes, which can sometimes be limited in performance wear.
Fjallraven Hoja Hybrid Shorts
Fjallraven is a company that makes wonderful collaboration products, and this is an example of that. Fjallraven and Hoja have come out with a biking line of products that I have eaten up. I plan to cover more of their biking products in future reviews. The Hoja Hybrid Shorts aim to perform on and off the bike. Mobility and multi-use functionality define the design and I like the shorter, tighter cut as a style choice.
Accessories
Shinola Canfield Sport Chronograph
This Shinola watch is in a league of its own. Its sturdy, immaculately crafted build leaves nothing to be desired in design. This Canfield Sport Chronograph combines traditional watch styling with sport-oriented features like a larger read-out and stopwatch. This watch doesn’t have all of the tech that some modern sport watches have, but it is a rock-solid watch that holds up in all conditions.
Suunto Vertical 2
On the other end of the watch spectrum, is the Vertical 2. This incredibly high-tech piece is built for extended adventures where you will need technical support from a watch. The watches in this series emphasise navigation tools, battery life and mapping capabilities. As someone who loves long hikes and long runs, this watch has been a great training asset. It can support all sorts of data from blood oxygen to how high you get off the ground between steps when running. It’s pretty impressive.
Smith Boomtown, Venture and Sliders
I’ve been wearing Smith sun glasses all summer. If I am out for a run, bike ride, work day, rafting trip or hike, I am wearing one of these pairs. Chromapop is a technology that Smith uses to truly make colors pop by increasing contrast. The Boomtown and Venture glasses also are conveniently polarized, which reduces glare and gives a sharp view when in the sun.
Lupine Blika
The Blika is an incredibly powerful, immaculately designed lamp. It boasts German engineering, and whatever the Germans are doing is, it’s working. This design is a high-output lighting system with multiple mounting options. I used it as a headlamp most and it has high, low, incredibly high, green and red light functions. You can control the light options with a small remote you can fit in your pocket if you mount the lamp somewhere out of reach. Its flexibility makes it useful across cycling, trail use and camping.
Skida Sun Tour Neck Gaiter and Packable Run Cap
For both the neck gaiter and run cap, I love how light-weight they both are. They are very portable and offer a lot of sun protection for how much space they take up. These can both fit in a fanny pack and be forgotten about until you need them. The mesh on the side of the run cap allows for great breathability, and they come in many fun designs and colors like Calypso, Odyssey and Snow Cat.
Darn Tough Men’s Frontrunner Micro Crew Ultra-Lightweight Running Socks
Darn Tough never disappoints and this time I wanted to try their ultra-light running socks. I ran a few 5-10ks in these socks and they were incredibly comfortable. They don’t grip the foot too hard while allowing for very little friction. With all Darn Tough socks, they also provide a lifetime warranty, so if they start to fail, mail them in to Darn Tough and you will get a new pair. Lastly, I also love the roadrunner on these.
Packs and Travel
Cotopaxi Allpa 50L Adventure Travel Pack
The Allpa is a truly innovative pack, where the top unzips and becomes its own sling bag. The design and organizational layout is impeccable, with intuitive pockets and robust zippers and stitching. The Allpa 50L combines suitcase-style organization with backpack portability, and has the whimsy fun colors that Cotopaxi always offers. The large storage capacity and travel-oriented design make it particularly useful for longer trips, hostel-jumping and backingpacking.
Buffalo Jackson Roosevelt Travel Duffle
Buffalo Jackson really puts out premium quality leather products, which is demonstrated with the Roosevelt. It is perhaps one of the most beautiful bags I’ve ever seen, which is complimented by its durability and functionality. Built from leather and metal fasteners, the Roosevelt Duffle favors durability and aesthetics over lightweight efficiency. But if weight is not your biggest concern, this is the Cadillac of travel bags. It feels designed for long-term ownership rather than minimalist travel.
Buffalo Jackson Roosevelt Laptop Bag
Similarly to the piece above, the Roosevelt Laptop Bag is simply a beautiful, sleek bag that combines traditional materials with modern organization. You can easily fit most laptops in here, which for OWAA, is a big plus. It is geared toward users who do some office work with a more rugged aesthetic.
Mission Workshop Control EPX Pack Kit 3
The Mission Workshop Control Pack is an urban commuter legend. Mission Workshop makes biking packs that are built to last with many innovative designs. This pack comes in different kits which satisfy different needs. I tested kit 3 which prioritizes extra space and waterproofing. This pack has been tested rain, shine and snow on the streets of Chicago and performed brilliantly. This pack is built around modularity and weather resistance, the Control EPX Pack targets users moving between city environments and outdoor use. The design emphasizes organization and adaptability.
Gossamer Gear Mariposa 60
The Mariposa 60 is an ultralight backpack benchmark. This nimble, sleek pack prioritizes lightweight efficiency without sacrificing carrying capacity. Large exterior pockets and long-distance comfort remain central to its design. I used this pack to train for future long thru-hikes, and the Mariposa has a very comfortable fit. The hip supports genuinely relieve weight in a balanced harmony with the should straps. On top of all the technical benefits of this pack, I love the mint green color it comes in.
Gossamer Gear LT5 Carbon Trekking Poles
Alongside the Mariposa, I used these trekking poles for training in Chicago. These poles prioritize low weight with their carbon build and they pack up easily for backpackers and long-distance hikers who go in and out of using poles. The poles have a corky grip that prevent blistering and the straps are easily adjustable.
RADL Pack 01
The Pack 01 is the perfect mix of reliability and comfort. While this pack isn’t ultralight, it has a hollow aluminum frame that is not cumbersome. From RADL, this pack was specifically designed not to fail, so if you are going on a long hike that could potentially rough up your pack, this would be the option to go for. This pack is intuitively designed with a floating lid specifically designed to hold a bear-canister.
Stio Cacher Hip Pack 2L
The Cacher Hip Pack offers compact storage for quick outings, long bike rides and daily carry. The padded strap offers remarkable comfort compared to some other hip packs and it is easy to forget that you’re wearing it. With the weight distribution sitting on your lower back, this pack is very comfortable to wear when riding a bike. Its size and layout prioritize accessibility over maximum capacity and it has become my daily adventure pack.