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How I Style Athleisure Sneakers

How I Style Athleisure Shoes

I go into the office 1-2 times a week, but I like to bring style when I do. I also appreciate comfort, so athleisure shoes are the only option. I don’t remember the last time I slipped on a pair of black or brown leather shoes.

Before jumping into my top picks, let me clarify what I mean by “athleisure” shoes. They’re not performance athletic brands like Nike or Adidas – though I’ll make very few exceptions. I’m probably the only person who would wear a pair of triple-white Halo Triple-White Kobe 8s or the all-white Air Force 1 Low A Cold Wall with nice pants and a quarter zip.

Take a peak below, and you’ll see why.

I define athleisure footwear as shoes that blend a casual style with an athletic fit. I’ll break down the models I use in my rotation in and out of professional settings.

My “Go-to” Athleisure Shoe Collection

I spend way too much money on shoes. And it’s getting more difficult to smuggle my shoes into the garage and get rid of the evidence before my wife notices.

That said, my most reached-for pairs of athleisure shoes are below.

All of these shoes are versatile, stylish, and comfortable. They pair well with chinos, jeans, tech pants, and joggers. They toe the line between athletic and refined, ideal for someone who values comfort and style like me.

While not budget-friendly, these shoes balance quality materials and design. They may cost more upfront, but their durability makes them a sound long-term investment. 

Boss Jonah Runn Sneaker


I’ll start with the Boss Jonah Runn Sneaker since it was my first foray into athleisure footwear. Visually, it resembles a running shoe with more bulk, pairing a thick midsole with an upper mixing faux leather, mesh, and nylon. The synthetic and rubber materials provide a durable yet breathable feel.

In terms of performance, the Jonah Runn delivers. Its lace-up closure secures the fit, while the EVA and rubber outsole grip surfaces. An extra foam layer in the midsole cradles my feet for all-day wear. I always incorporate these into my professional fit, thanks to the refined combo of gray and black.

My one sticking point is the price – the Jonah Runn retails between $150-175. It’s an investment, and you’ll take a hit on your bank account. But the high-grade construction guarantees longevity versus cheaper pairs that wear out quickly. For the quality and versatility, I find them worth the cost. And they go with virtually everything in my closet.

On Running Roger Centre Court Shoes

Next in my rotation are the On Running Roger Centre Court Shoes, created in collaboration with tennis icon Roger Federer. Inspired by classic tennis sneakers, these feature a perforated faux leather upper for breathability and signature On CloudTec cushioning in the outsole.

I bought the crisp all-white shoes with gold trim. The padded interior sleeve prevents sliding around, while the CloudTec system provides a lightweight yet supportive feel during all-day wear. I can move easily in these, whether giving a presentation or meeting clients over coffee.

My main hang-up is the $189 price tag, which is standard for the Swiss running brand. But as an avid Roger Federer fan, I can justify the splurge for a piece of sports history meeting modern technology. The look also stands out from standard casual shoes on the market – I always get compliments when I wear these distinct kicks.

Wolf & Shepherd Crossover Victory Trainer

Continuing my affinity for crisp white athleisure shoes is the Wolf & Shepherd Crossover Victory Trainer. This lace-up model blends genuine leather, mesh, and rubber for a polished yet sporty look. Touches like the Italian leather trim and foam-injected scuba lining nod to fine craftsmanship.

I usually wear these shoes for weekend errands, date night with the wife, and to the office. Features like the premium rubber sole, shock-absorbing cushioning, and soft leather ensure all-day support during extended wear. The crossover name says it all – this transition seamlessly from active endeavors to professional settings.

The $269 price lands on the high end. These are the most expensive shoes in my sneaker arsenal. However, the price reflects Wolf & Shepherd’s commitment to quality components. Given how often I incorporate these into my rotation, I don’t mind the investment. The white-on-white colorway also maintains a clean, sharp aesthetic that works year-round.

The only challenge is keeping them clean.

Cole Haan Grand Crosscourt Sneakers

Another white pair – the Cole Haan Grand Sneakers get their fair share with my fit. Cole Haan is known for merging classic style with sporty soles, evident in this lace-up model. The upper mixes premium materials like genuine leather and suede, while the GRANDFØAM footbed offers cushioning for all-day wear.

I appreciate little touches like the textured sidewall and contrast heel counter. The low profile gives it a sleek feel, though the outsole still grips well on various surfaces. 

Compared to other leather athleisure shoes, these retail for less than $100 on Amazon.

The white leather pops against both casual and business casual attire without veering too athletic. Easy to break in and style, the Crosscourt Modern is my weekday for everything from client meetings to social events straight after the office.

My Go-To Office Pants

I have a standard rotation of office pants I like pairing with my athleisure shoes. My current favorites come from brands BYLT, Vuori, and Public Rec for their materials that balance comfort and mobility with a tailored fit.

The BYLT Pant

One workwear staple is my BYLT pants – I own almost every color. The stretch fabric moves quickly while retaining a flattering slim fit through the leg, though the hem runs a little long on me. I had to take them to my local dry cleaners to adjust the length just above the ankle, showcasing my shoes perfectly.

Available in versatile solids like black, navy, and gray, these adapt well to business meetings and after-hours events. The all-black pairs complement my athleisure kicks, letting the shoes take center stage. And, the moisture-wicking material makes these breathable whether I’m tackling a full day of clients or traveling to Chicago.

Vuori Ripstop Pant

In the same vein as BYLT, another go-to pant is from Vuori. Their Ripstop Pant is clutch. These stand out for the lightweight yet durable ripstop fabric, which is soft against the skin and flexible enough for all-day movement.

My usual colors are classic charcoal gray and earthy sesame tan. The neutral tones pair easily with my full sneaker rotation from crisp white leather to understated gray mesh. And the stretch mesh fabric doesn’t wrinkle, making this ideal for travel days or last-minute client visits.

I reach for my Vuori Ripstops when comfort is critical, but I still need to look sharp. The streamlined profile creates a tailored fit that works in professional settings, while subtle design features like the zippered pockets and drawcord hem add uniqueness. They’re my weekend chill pants that still work for impromptu meetings, which always happen.

Public Rec All Day Everyday Pants

My most recent addition for ultimate comfort is the Public Rec All Day Everyday Pant. I’ll admit, I only have one pair so far – the versatile Stone Gray. But these feel like wearing pajamas all day, thanks to the mega-soft, four-way stretch fabric.

I specifically keep these on hand for long Caltrain commutes into the office. Pulling them on feels like sliding under the covers at home instead of prepping for a cramped train ride. Yet the tailored cut still looks polished with a hem hitting right at my shoes. Out of all my go-to’s, these receive the most double-takes and “Where did you get those?” questions when paired with my Crossover Victory Trainers.

My Go-To Tops

First and foremost, you’ll notice a trend – BYLT tops are my staples for the office and going out. I’ve become a devoted fan since discovering them on Instagram in 2020. Between quality materials and fit, BYLT retains comfort while elevating my style. I incorporate their shirts, pullovers, and jackets with all my pants and sneakers.

BYLT Elite+ Fairway Drop-Cut Pullover

The Elite+ Fairway pullover is an MVP for transferring from professional settings to dinner with fellahs. I own black, storm gray, and heather gray – all colors that pair effortlessly with my shoes. The drop-cut hem provides great coverage at my waistline, complementing tailored pants and relaxed denim on my off days.

Despite the golf-inspired name, I receive compliments whenever I wear these. The moisture-wicking fabric keeps me cool, while the mock neck adds unique flair versus a standard crew. I’ll throw on a Fairway over everything from button-downs to tees when it’s time to get casual.

BYLT Coastal Overshirt

My latest BYLT addition is the Coastal Overshirt, which I broke in during my birthday trip to Napa last December. Its longer fit layers perfectly over slim tees, while the chest pockets and corded collar play up subtle accents.

Long Sleeve Henley with ASRV Waterproof Vest

For colder months, I rely on long-sleeved henleys as my base layer, specifically from BYLT and Nordstrom brands. The henley placket adds visual interest to an otherwise basic shirt. But the real hack is layering with a sleeveless vest on top.

My go-to is the ASRV waterproof vest – it retains heat while protecting my core against the elements. I also own a similar vest from Lululemon that packs down easily for traveling and commuting. The sleeveless cut leaves my arms free while keeping essential organs shielded.

The henley and vest combo feels much more pulled together than just wearing a hoodie. It brings outdoorsy performance to my business casual aesthetic. I’m covered enough for crisp Bay Area winters without sacrificing style points. And it showcases my athleisure footwear perfectly.

Jackie Premium Fleece Quarter-Zip Hoodie

Quarter-zip hoodies are tough to find from athleisure labels. While I own some from Nautica, stock options are limited. But I have one on my wish list: Normal Brand’s Jackie Premium Fleece Zip Hoodie.

I like how it brings the tailored look of a quarter zip with the comfortable feel of a hoodie. Perfect for outdoorsy weekends while running errands or watching the Lakers game with friends. I wish they offered more than three muted colors, though – expanded shades would increase versatility to pair with my shoes.

But based on materials alone, the Jackie Premium seems ideal for layering during transitional weather before shedding down to a tee or polo. Once I evaluate my wardrobe gaps for spring, this is high on my consideration list to test out.

B. Draddy Procter Hoodie

Another hoodie on my radar is from LA brand B. Draddy – namely, their Procter design. This one captures a more athletic essence with the kangaroo pocket and contrast zipper tracks. I’d wear it over performance tee brands like Ten Thousand and Vuori for weekend getaways or music festivals.

My hesitancy lies in the $200 price tag, which is steeper than other hoodies I own. But the premium Italian fabric and subtle branding suggest longevity over fast fashion alternatives. Before pulling the trigger, I’d want to try it in person to ensure the correct slim fit. But the Procter could level up my casual look with white leather low tops.

Before You Go …

As someone splitting time between home, commutes, and office visits, adaptability is everything in my wardrobe. The athleisure trend has been a game changer in letting me move quickly between different environments without sacrificing style or professionalism.

I’m no fashion expert – I simply understand which fabrics, fits, and styles enable me to transition to everything I have going on in my life, personally and professionally. But the regular compliments I get on my kicks and ‘fit let me know I’ve found an athleisure uniform that works. When style and comfort unlock better confidence and performance, I’ve validated my choices through experience rather than chasing trends.

My philosophy is that all-day comfort lays the foundation – if my body feels restricted or uncomfortable, my confidence and work suffer. Materials with stretch and breathability ensure I stay unrestricted whether in 4+ hour Zoom meetings or last-minute client visits that turn into evening dinners. Having that flexibility with tailored cuts gives me the versatility to go from train rides to headlining presentations or client meetings.

With options from brands that blend high performance and refined aesthetics, I can merge once-disparate elements of business attire and activewear. My favorite athleisure shoes epitomize that duality, supporting walking San Francisco streets while projecting open and trustworthy body language in business settings. Feeling good in clothes adapted to my lifestyle enhances trust and approachability with colleagues and leads. 

The beauty of today’s options lies in artfully blending, not sacrificing, comfort and professionalism through versatile hybrid techwear. I’m excited to see how the athleisure market continues innovating in the coming seasons.

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