Office to Afternoon Rooftop Outfit: 1 Look, 3 Budgets

Office to Afternoon Rooftop Outfit: 1 Look, 3 Budgets
From breezy daylight to city lights, we’ve got your rooftop style covered—one look, three budgets, endless confidence.

Golden hour with good friends and a good drink as we head into the busy season. It's the kind of night where a bit of breeze catches up with you as the sun goes down, and you’re glad you layered just right. This outfit is about making those transitions seamless, keeping you looking sharp without making it look like a chore.

In this series, we’re all about showing how you can put together the perfect outfit across different budgets. Pieces like a sleeveless knit polo that works on its own for warmer fall days or under a light layer as things cool down. Tailored chinos that walk the line between casual and dressed-up. Every piece here is doing double duty—keeping you comfortable while making sure you’re ready for whatever the day has in store.

men's fall outfit collage with sweater polo, chore coat, chinos, woven belt, and penny loafers
Fall men's outfit idea with sweater polo, khakis, and penny loafers

Sweater Polo

Recently, we featured the long sleeve navy sweater polo as a surprise fall staple. The sleeveless knit polo is also a perfect base layer for warmer afternoons. It retains the thicker knit quality for temperature and style, and wears easily under a chore coat when things get chilly. Look for subtle details like a contrast collar or tonal stripes to add visual interest without overcomplicating the look.

old navy sweater polo

Old Navy Striped Sweater Polo, $23 $45

Express Johnny Collar Polo, $28 $74

marine layer sweater polo

Marine Layer Sweater Polo, $108

Chinos

Chinos are a smart casual essential. Here we opted for a lighter sand color with an extended tab button closure—these small details give the outfit a touch of classic sophistication without feeling too formal. A tailored cut keeps them neat without being restrictive, making them adaptable for different settings.

These have been featured a number of times before and regularly show up in our deals posts as solid buys.

Nautica Chinos, $38 $44

Bonobos tan chinos

Bonobos Italian Chinos, $62.30 $128

Proper cloth chinos

Proper Cloth Di Sondrio Stretch Cotton Chino, $195

Braided Leather Belt

A braided belt introduces texture that enhances the minimal outfit without overwhelming it. It’s a simple accessory that adds cohesion by connecting the sweater polo to the casual chinos with the loafers.

J.Crew leather woven belt

J.Crew Factory Leather Belt, $34.50

LLBean leather belt

LLBean, $55

todd snyder leather woven belt

Todd Snyder O-Ring Braided Belt, $158

Chore Coat

If things are already getting chillier where you are, or you need to carry a layer for the mercury swings, a chore coat makes a smart addition. While a blazer would also work well with this outfit, the chore coat is used here to add a blazer-like layer without going too dressy. The sweater polo, dressier chinos, and loafers can lean either casual or formal, depending on what they're paired with, and the chore coat helps balance the outfit towards a more relaxed, casual vibe.

getup illustration
Target Chore coat
First featured in our recent Target, Old Navy, and Amazon fall style finds guide

Goodfellow and Co. Flat Collared Shirt, $35

Taylor Stitch Chore Coat

Taylor Stitch Ojai Chore Coat, $188

Buck Mason chore coat

Buck Mason Omaha Flyweight Fatigue Shirt, $228

Loafers

These chinos are no stranger to penny loafers. Both the pants and shoes were featured a few months back in our Chris Pine outfit re-make, but there, when paired with a white t-shirt and denim jacket, you get a classy 80s-inspired casual style:

Denim jacket outfit
See our 37 favorite denim jacket outfits in our massive outfit swipe file
nunn bush loafers

Nunn Bush, $79

gh bass loafers

GH Bass Weejuns, $175

allen edmonds randolph

Allen Edmonds Randolph, $425

What do you think? Chat with me in the comments below

Andrew Snavely

Andrew founded Primer in 2008 and brings 15+ years of men's style expertise. Known for his practical, relatable approach to style and self-development, he has been a recognized speaker at conferences and has styled work for top brands. Off-duty, he loves photography & editing, and enjoys road trips with his dog, Leela. Raised in rural Pennsylvania, educated in DC, and living in LA for nearly 20 years, Andrew's diverse experiences shape the relatable and real-world advice that has helped millions through Primer. On Instagram: @andrewsnavely and @primermagazine.