My 7 Secret Tricks for Dressing “Nice” in Summer

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Picture any season but summer and think about what you would default to wearing if you wanted to look put-together and sophisticated. It doesn’t have to be dressed up, but it’s dressier than casual. I feel safe guessing that it includes some type of jacket like a blazer, bomber, or trucker, some form of long sleeve button up shirt, nicer pants or darker denim, and some kind of boot or dressier shoe.

Now picture what you would wear if you had to go to the same dress-level destination in the sweltering summer heat on August 1st. Maybe it’s a work function. Maybe you’re going to a four dollar sign restaurant while on a tropical vacation. Maybe you got invited to some trendy launch event from a friend of a friend.

If you’re mind goes blank, you’re not alone. Dressing well in summer is one of the most common things I get hit up about. For guys that live anywhere with more than two seasons, we default to layers and thick, textured fabrics – and lots of them – to build refined, cohesive outfits.

In summer, all of that goes out the window. But, here’s a little fun motivation: learning to dress well with the limitations of the hot season will noticeably improve your overall style for the rest of the year.

Here are 7 of my summer principles for making my summer uniform more put-together for dressier occasions:

1. Wear more refined versions of your summer go-tos

For many of us, sneakers are the shoe of summer, and there are some classics like canvas options from Vans and Converse that will pound pavement for you through your sunny months.

But when it’s 7PM and you’re getting ready to go somewhere, you may find paired with your pared down summer clothing, a pair of Vans Classics doesn’t seem put-together enough for the nice place you’re going.

In that case, swapping the canvas Vans for black suede slip-ons keeps everything you like about your just-kickin’ it shoes, but noticeably augments the outfit to something more intentional.

Similarly, keeping everything else in your outfit the same, swapping out your flip flips for a leather sandal immediately upgrades the look from oceanside to an evening appropriate outfit.

2. Lean on simple, enduring styles

I often see guys end up doing too much because they're trying to make up for a lack of layers and material choices. A bright coral pink linen shirt with an intricate and colorful swim suit. Vivid shirts, shorts, and canvas sneakers all in completely different colors. I’m not opposed to bold colors, but when looking to build an outfit that looks more refined, as they say, less is more.

Just like with our recent Chris Pine outfit rebuild, starting with items that are classic and simple naturally create a more sophisticated outfit. To whatever degree that feels “boring” to you can be augmented incrementally, as Pine did with his rectangular watch, braided leather belt, and fuller cut chinos.

Bold or vivid colors and patterns are right at home in summer. To do it well, consider employing an emphasis hiearchy. Choose a bold item to highlight in your look, and build out the rest of the outfit with more subdued pieces that enhance the bold item, instead of fighting it or compounding it:

In summer, that could mean a uniquely patterned short sleeve shirt with neutral-hued shorts or pants. Or it could be bright teal chino shorts with a white oxford shirt and brown loafers. If you’re ever looking in the mirror and unsure if you’re attempting to do too much with your summer fit, try swapping just one item for a more subdued alternative and check again. If it feels balanced and cohesive, you’re good to go. Repeat as necessary.

3. When you want more splash, turn to vintage/retro trends so you’re calling on menswear from past eras, which are inherently more dressy

The summer months can feel a little repetitive: Polo, shorts. T-shirt, shorts. Short sleeve button up, shorts.

When you want to inject a little punch into a summer outfit, my personal move isn’t to go wild with bright colors or trend-chasing styles, it’s the opposite. I like to lean on vintage or retro designs, calling on past eras from menswear.

Lots of great options have become increasingly mall-accessible over the last few summers. Knit polos with interesting textures and tipping take your standard polo look from sporty to suave. Grail brands like Todd Snyder are the go-to for celebrities and the otherwise financially inclined but more affordable options are available if you’re willing to look.

Abercrombie & Fitch has become one of my favorite summer shirt stores thanks to their rotating offering of unique, retro-inspired knit polos and button ups. The Tie Bar is probably the safest, budget-friendly option, which is something I’m excited to see.

For bottoms, flowier pants like the linen ones we recently featured instantly add a touch of retro Riviera. For shorts, going with a shorter inseam, cuffs, or pleats all introduce visual callbacks that enrich the way your shirt and footwear appear in your outfit.

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4. Add Structure to a Structure-less Season

With traditional professional and formal wear, there is an emphasis on structure and silhouette, with both virtually absent in summer clothing. On the far end of formality, with things like tuxedos, dress military uniforms, overcoats, crisp standing shirt collars, and perfectly knotted ties, sophistication is delivered with a detailed balance of rigid form and elegant drape. Drape is the quality of how clothing hangs and moves on your body.

With summer, all emphasis is placed on a flowing and rakish drape. Classic summer menswear staples include loose linen shirts and fluid, unbuttoned silk-like resort shirts. The looseness and thin material allows movement and airflow.

But sometimes that thin material can look too casual, for instance, in the collar area because it flattens out under its own weight.

A dead-simple way to dress up your summer clothing is by adding structure. For example, wearing a polo with floppy collars looks casual and possibly even sloppy. Having a linen shirt's collar go any way it wants in the sun is fine but casual.

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5. Shop from the middle out

Personally, I prioritize buying things that “live in the middle.” Either because of their design or how they interact with the other outfit elements, these items can be dressed up OR worn casually. I refer to this as “shopping from the middle out.” I still buy only-casual or only-dressy pieces sometimes but I’m always drawn to this priority of versatility.

I do this all year, but it’s especially important in summer.

Unless you live somewhere hot and sticky most of the year, your summer-only clothing likely gets worn more frequently but for less of the year. This makes the case for buying not only designs that are versatile, but also nicer versions of these things. The benefit is you can then incorporate these into other seasons (linen shirts in spring, knit polos year round) even further justifying investing in these better versions.

Now you’ll start building a wardrobe that is not only easily pairable with one another within a specific season, but also when building outfits in other seasons:

One of the best parts about shopping from the middle out, is “how dressy they appear” is controlled predominantly by what footwear you choose for a Getup.

Wear a retro-inspired knit polo with beat up white vans and you have a cool, casual day look. Pair them instead with a premium suede loafer and the entire outfit feels refined and evening ready. Generally speaking, it requires more effort and expertise to take a very casual or very dressy item and pull it the other way. Beginning with a middle out mentality requires a lot less computing power when you’re rushing to pack before summer vacation.

6. There are 2 ways for combating heat when making summer outfits

More than any other season, getting dressed in the summer prioritizes reducing the discomfort of making a hot sun hotter.

You have two options for optimizing being comfortable in high heat while maintaining some semblance of your personal style: Wear different, summer appropriate items (e.g. shorts over jeans):

or wear the same thing as always but with swaps for their summer versions (e.g. linen pants over jeans):

In this outfit, I've swapped the white long sleeve dress shirt for a silk short sleeve camp collar shirt, the cotton dress pants for linen pants, and brown suede boots for suede loafers.

In summer, swap your…	…for:
jeans	chino shorts, pull-on shorts
chinos and dress pants	linen pants
Wool suit	linen or cotton suit; linen blazer over a polo with lightweight chinos
button up oxford shirt	Short sleeve resort shirt; knit polo
dress shoes or boots	leather loafers or leather slip on like huaraches
Sweaters	loose knit button up shirts or polos
Jackets	Unlined cotton or linen versions

7. Embrace Jewelry

Lots of guys stop at sunglasses, wedding ring, and a watch, but accessories can add a lot to an outfit, especially a low key one, like the rectangular watch and bold sunglasses in the Chris Pine outfit I mentioned earlier.

For a long time, men’s jewelry in specific forms has only been embraced by certain subcultures, economic classes, or the fashionably fearless. In the last few years, the guardrails have really come off on what is and isn’t “acceptable” for day-to-day wear.

And it’s not just “who” can wear it, it’s how to wear it. Wearing both metal colors, multiple rings or bracelets, and simple chain necklaces can be mixed and matched as desired.

Nobody does that better than Primer style contributor Daniel Baraka, who regularly includes multiple pieces of jewelry in the outfits we feature to great effect. It never feels flashy or out of place, and we’ve previously discussed his personal connection to some of the pieces, which make wearing them that more meaningful.

Start slow and simple, if you’re curious. A narrow metal cuff bracelet or simple chain necklace adds degrees of character to a classic and minimal outfit.

What are some of your summer style tricks? Keep the list going in the comments below!