Men’s Summer to Fall Outfits

If you know how to do it, you can pull off wearing these three pieces all year.

Rack of men’s summer and fall outfits
Post by Trunk Club
September 5, 2019

A wardrobe is no good if you need to replace it entirely every three months—especially if you live in a place with temperamental in-between seasons. The trick is to have a handful of pieces you can wear for several seasons. Here’s what to wear when you’re transitioning your closet from summer to fall.

Men’s Fall Trend #1: Dark denim

Why we love it: They’re a Jack-of-all-trades and one of the hardest-working pieces in your closet.

For summer: Wear a nautical-inspired T-shirt with brown leather sandals. (See if you can snag some time on a boat, too.) Cuff your jeans for an East Coast feel or roll them even higher if you want to dip your feet in the water.

Into fall: Use dark denim as a foundation piece. To build a casual fall work outfit, layer a utility jacket over a long-sleeve henley and toss on a pair of chukkas.

Men’s Fall Trend #2: Long-sleeve button-down

Why we love it: Having a solid rotation of these will last you for months and years.

For summer: Instead of wearing jeans and a tee, swap the lengths and try a long-sleeve shirt with shorts. You get a similar amount of warmth and coverage, and you can always roll up your sleeves if you’re toasty.

Into fall: We’ve talked about color blocking before, and this is another great opportunity to explore with colors you may not think complement each other. For example, pink and earthy green balance each other on the color wheel. We promise, it works.

Men’s Fall Trend #3: Statement sport coat

Why we love it: Because they’re cool and every guy should have one that feels unique to him.

For summer: Think about accessories. White shirts and medium brown leather feel like classic summertime. Then add on some sunshine-y touches with a bright yellow tie and a sky blue pocket square.

Into fall: Trade your brown shoes and belts for black in a more formal setting. Keep your pants neutral and let the pattern on the sport coat do most of the heavy lifting.


Our stylists are trained to build you a wardrobe for any season. If you want to learn how to transition summer clothes to fall, send them a message.

At Trunk Club, our stylists help people build their best wardrobes by discovering what fits their body, their budget, and their personal style.