Styling Shorts: 2 Simple But Effective Outfit Templates

It's all about the proportions.

This morning I asked Siri to remind me to schedule an appointment for a leg wax. Shorts season is upon us! Today I will be sharing two of my favorite shorts silhouettes, along with my go-to, foolproof templates for styling them. Before I dive in, I just want to emphasize that the below ideas — as the title of this newsletter suggests — are extremely simple. The point of them isn’t to be revelatory, but rather, to be reliable. The latter quality is particularly valuable when doing things one often does during shorts season, like trying to pack for a weekend away in a tiny suitcase, or throwing on an outfit to get impromptu gelato.

#1: Mid-thigh or knee-length high-waist tailored shorts + belt + fitted cropped tank

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The Shorts

I have two pairs of longer, high-waist, tailored linen shorts that I wear constantly. The white ones are from a brand called Hej Hej, and the black ones are from Modern Citizen (a brand I’ve now mentioned in multiple newsletters because they make such great under-the-radar basics). Sadly neither sells these exact styles any longer, but I found one pair of the Modern Citizen ones on Poshmark in size small for $85. ***They run a full size big, FYI, so would fit you if you’re usually a size medium!*** Similar pairs from other brands I found include: these from Benetton for $74, and these from Bali Lane for $105 (which notably go up to a size 3XL).

The Belt

Pretty much any belt you have lying around will do the trick, but if you’re in the market, Etsy has many options. Here’s a classic brown one for $43. I also love these embroidered Argentinian polo belts, each $67.50.

The Cropped Tank

Likewise, you may very well have a tight-fitting cropped tank already in your wardrobe (a tight-fitting tank that isn’t cropped would also do just fine). The ones I’m wearing above are from Aritzia and sell for $25. I bought them with a gift card I needed to use, so they weren’t my most carefully vetted purchase of all time, but I liked the high neck and the 100% cotton fabrication. I wish the material wasn’t so thin and that the hem wasn’t raw, but otherwise they get the job done. Here’s a similar alternative from Kotn (with a finished hem and what looks like a thicker i.e. better quality cotton) for $35.

#2: Short track or boxer-style shorts + long tunic-style shirt that *almost* covers them

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The Shorts

In the photos above I’m wearing old running shorts from Nike and New Balance, respectively. Do you own a pair of short, solid-color track shorts without any obvious logos? Then you’re good to go! Short cotton boxer-style shorts would also work here. (In an ideal world the shorts you’re styling with here have a dolphin hem, which means a hem that slants upward slightly near your outer thigh, but it’s not a dealbreaker if they don’t). Otherwise, I found a very solid option for $16.50 and with sizing up to 3X from my favorite luxury brand Dick’s Sporting Goods. There are a ton of color options, but for maximum styling potential I’d go with black, white, or red.

The Long Shirt

Poke around in your closet for shirts that hit a few inches below your hips. Sometimes it’s hard to tell which ones are going to work, proportionally speaking, until you try them on with the shorts you’re planning to wear. When in doubt, channel our girl Goldilocks: At or above your hips = too short. Long enough to entirely cover the shorts you’re wearing = too long. Somewhere in between = just right. The shirt should also have a bit of structure to it — anything clingy or form-fitting around the hips isn’t going to achieve the desired look. “Tunic” is a useful keyword in this case, and Marni and Tory Burch are great brands to include in any secondhand search. Here are some shopping leads that look promising:

1. Black Long-Sleeve Tory Burch Top, Size 2, $80

2. Striped Polo Ralph Lauren Top, Size 10, $120.84

3. Green and Cream Missoni Top, Size 6, $103.75

4. Yellow Short-Sleeve Tory Burch Top, Sizes XS - M, $196

5. North Style Chambray Top, Sizes S - 3X, $64.95

6. Black Marni Top, Size 4, $63

7. Cream Altuzarra Top, Size 12, $54

8. Pink Marni Top, Size 4, $80.50

And it goes without saying, but: The beauty of a simple outfit template is that it’s ready and waiting for your personal stamp. Accessorize accordingly!

xo Harling