How to Build the Perfect Trail-to-Town Outfit

Find functional benefits hiding behind a fashionable facade with each of these transitional pieces that will take you from hike to hangout in no time.

Hikes are clearly our jam here at REI Co-op: We love everything from short jaunts on local trails to epic summit pushes that begin predawn and end after dusk. We also love post-hike breakfasts, brunches, coffees, beers, snacks and dinners. But that less-than-graceful shimmy out of functional hiking duds into more fashionable attire in the backseat of the car before heading for a nosh in town? Not exactly the best part of the day.

The same goes for those before- or afterwork hikes: It’s tougher to commit to the outside time off the clock when you have to pack an extra outfit (and change in the office bathroom). 

Thankfully, more brands are developing apparel that folks want to wear out just as much as outside. From button-downs with wicking properties to snugly fleeces with funky, retro patterns, it’s much easier to find pieces that transition seamlessly from trail to town (or vice versa).

We go over the properties you’ll want to look for as you build your go-anywhere outfit, and offer some of our top picks in each category. Choose correctly and you’ll never have to suffer through another backseat shimmy again.

Tee George is smiling and seated in front of a large waterfall.
On the trail, REI partner Tee George is wearing REI Co-op Trailmade shorts, REI Co-op Sahara shirt and Danner Mountain 600 Leaf hiking boots.

Technical Top

We love Saturday mornings that start with a group hike. Everyone meets at the local coffee shop, sets out to the nearby trailhead (ideally by foot), chats their way through the miles and returns to the starting point for some post-adventure grub and another shot of caffeine. When your hike turns into an all-day hangout, you want to both feel comfortable and look the part in every setting. Moisture-wicking, sun-protective fabric is a must for warm, sunny or challenging hikes. You’ll also want to choose pieces that breathe, stretch and easily pull double-duty as business casual attire (which is much easier now than ever before).

The crisp workwear look, wicking qualities and UPF 50 ratings of both the short-sleeve REI Co-op Trailmade shirt ($49.95) and Mountain Hardwear Stryder long-sleeve shirt ($89) make them perfect for more casual day hikes with before or after plans. One member-reviewer from Kansas loves the subtly heathered print on her UPF-50-rated REI Co-op Sahara Shade hoodie ($49.95) and says, “It’s so soft and comfy that I started wearing it to work.” Looking for a little unexpected hit of pizzazz on a hotter-weather hike? We like the strappy back and built-in bra of the quick-drying Talus tank top ($75) from Black Diamond. Read more about layering in Layering Basics.

Fleece Mid Layers

With its can’t-beat hand feel and insulating properties, fleece mid layers are a shoo-in for any hiking kit, and lighter-weight versions tend to be easily stuffable into a daypack if the weather warms up. For trail-to-town versatility, you might consider a jacket or pullover that has a relaxed fit and pockets, including a zippered or snapped pocket for those can’t-lose items.

We love the bright colors and secure storage (zippered hand pockets and interior drop-in pockets) of the Trailmade fleece jacket (men’s and women’s, $59.95) and Trailmade fleece vest ($49.95) from REI Co-op. The Lightweight Synchilla Snap-T fleece pullover (women’s and men’s, $129) from Patagonia is another easy-fitting option that falls a bit lower on the hip for extra coverage outdoors. Look for recycled polyester fleece when possible. (The items listed here feature it.) Read our other top picks in The Best Fleece Jackets of 2023: Staff Picks.

Windbreakers and Rain Jackets

Performance is pivotal for outerwear, but that doesn’t have to mean your top layer needs to be bulky and frumpy. Look for options that effectively block the wind, offer free range of movement and include a hood. Because jackets often get shed when you warm up and stashed once you step inside, you might consider one that stuffs down to a packable size.

The Trailmade Soft-Shell Anorak (women’s and men’s, $99.95) from REI Co-op, for example, features a breathable stretch-nylon double weave shell in a hip silhouette with creative color-blocking. The Cielo rain anorak ($155) and Cielo rain trench jacket ($200) from Cotopaxi offer fully taped seams and PFC-free durable water repellent—especially great if a downpour is in the forecast. To learn more about hiking in rainy conditions, read How to Go Hiking in the Rain.

Hiking Pants

Tee George smiles as she walks down a street in town.
Back in town after a hike, Tee George wears Outdoor Afro Inc + REI Co-op Trail Pants and Trail T-shirt and sneakers by Merrell.

There’s nothing inherently wrong with traditional, over-pocketed khaki pants. Sure, they do carry a certain je ne sais quoi—as in, je ne sais if he’s going fishing, safari exploring or on a corporate retreat. But today, your options for hiking pants are practically limitless. You’ll want to choose pants that fit your hiking style: Leggings and joggers are lightweight and stretchy options for casual treks or warmer days, while a chino-like style may offer a more tailored fit with durable or reinforced material for technical outings.

For a less-strenuous hike, the ruggedly good-looking Rydr pants ($99) from KUHL feature trail-approved articulated knees and reinforced rear cuffs—though their cotton twill construction is not ideal for moderate to hard trails. The cropped cut and flattering fit of the lightweight, stretchy Mountain Hardwear Dynama/2 ankle pants ($85) are a versatile workhorse too: They work just as well with hiking boots as they do with a pair of wedges.

Hiking Shoes, Sandals and Socks

Reliable traction, solid arch and/or ankle support and a durable exterior are nonnegotiable when it comes to choosing trail-worthy footwear. After all, you want to walk back to the starting point, not hobble there. For options that are town-ready too, seek out kicks with sleek lines, suede or leather details and fun color-blocking.

Danner expertly walks this line with its snazzy, lightweight Trail 2650 mesh hiking shoes (women’s, $169.95), featuring Vibram® 460 outsoles with Megagrip technology, and the durable, breathable and modern Trail 2650 GTX hiking shoes (men’s, $189.95), which has waterproof/breathable GORE-TEX® lining under its leather and textile uppers. Merrell’s MQM 3 hiking shoes (women’s and men’s, $120) are another great choice: One member-reviewer from Texas said her first 8-mile hike in them gained nearly 900 feet of elevation. “The treads gripped the limestone rocks without issue and I never felt like my foot could lose traction,” she says. See our other favorites in The Best Hiking Boots of 2023: Tested.

Your shoes are only as comfortable as the socks underneath them: Wool and synthetic materials offer insulation, wick moisture and dry faster than cotton. In warm conditions, opt for lightweight socks with little to no cushioning. For cooler days, longer and rockier hikes or scrambles, more cushion might be better. We like finishing the outfit with a pair of colorful socks like the Hike Light Cushion Great Excursion Print crew socks ($24) from Smartwool or the Sunset Ledge Micro Crew lightweight hiking socks ($24) from Darn Tough for a final touch of peekaboo style. Learn more in How to Choose Hiking Socks.

If you’re a sandal-lover and plan to cover miles over dirt and rocks before hitting the pavement, make sure your footwear is up to the task. Flip-flops and other slip-ons are a definite no-no: You want a pair that fits snugly, offers some support and won’t get dangerously slick when wet. Look for sandals with a thicker sole, secure webbing and some arch support, but if you’re headed out on the town afterward you might want to avoid burly toe bumpers and overly aggressive lug patterns. And since we like to splash in mud puddles instead of dodge them, we look for options in darker colors that are less likely to stain.

We love the timeless look, custom-fitting double straps and podiatrist-approved footbeds of the Chaco Z/2 Classic Sandals (men’s and women’s, $100), which come in a variety of classy and sassy colors. Browse our other favorites in The Best Hiking Sandals of 2023: Tested.


Keep the rays (and bad hair days) at bay by choosing a hat that transitions from your sunny hike to afterward libations. Look for brimmed toppers made from wicking fabrics like nylon and polyester (not cotton or linen), as well as those that feature mesh or loose crochet stitching for breathability. We’re also fans of large, floppy brims, which offer sun coverage and add a just-right touch of stylish whimsy. For chillier weather, a wool or synthetic beanie can help your head—and consequently the rest of your body—retain heat. Crushability is key if you want to stuff your hat into a daypack.

Two hats to try: The look-at-me color scheme of the unisex Cotopaxi Altitude Tech 5-panel hat ($35) works for staying visible in the woods and catching eyes at the pub. We also like the refined look and all-over sun coverage of the Levanzo Raffia big brim sun hat ($69) from Scala.


Yes, you’re wearing a hat. No, that doesn’t mean your eyes are fully protected from the sun. Given overexposure to UV rays can lead to cataracts, corneal damage and ultimately decreased vision, don’t mess around with unprotected peepers. The Centers for Disease Control recommends selecting shades that, at a minimum, block both UVA and UVB rays. (UVA rays can damage retinas, while UVBs pose a threat to corneas and lenses.) Our favorite shades offer additional benefits too, like glare-reducing polarization and grippy nose pads that reduce frame bouncing. Gone are the days when intense, sporty wraparounds were the only sunglasses options for outdoorsy folks: Now there are plenty of polarized options in a wide range of styles and price points.

The Lowdown 2 sunglasses from Smith (starting at $189) combine a contemporary, rectangular tortoise shell frame with polarized lenses that feature a vacuum-applied antireflective coating to further reduce glare. (They’re available in Slim and XL sizes too.) On a budget? Go for the funky, durable Circle Gs polarized sunglasses ($25) from Goodr. Our editor’s pair gets compliments on the regular. Learn more with How to Choose Sunglasses.


Why just tell time when you can track your blood oxygen levels, create an interval workout that syncs with your smartphone and tracks your position using GPS? Today’s smart watches are enough to make a 1960s-era James Bond envious. And unlike previous sport watches that were so clunky and button-loaded they looked like one errant button-press might launch you into space, there are plenty of sleek, understated options you can wear from hike to hangout. Look for a watch that’s water-resistant or, better yet, waterproof, with an easy-to-use interface. Longer battery life or rechargeable batteries are always a bonus: No one wants their timepiece to conk out on a trek when they’ve got a date to meet up with afterward.

The 9 Peak Pro ($549) and 5 Peak ($300) from Suunto both feature a streamlined silhouette, low-profile face and simple watchband that belie functionally (including route recommendations and GPS tracking) worthy of the next 007.

For more information, read What to Wear Hiking.

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