#OOTD: How to Dress for a Rainy Spring Day

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

If you’ve been keeping up with the #OOTD series here on The Style Guide, you might notice that the outfits as of late have leaned more casual (if a tailored look is what you seek, head here). Perhaps it’s the shifting climate that has this menswear writer more geared toward shorts, perhaps it’s the effects of a stylish trip to Florida, or perhaps it’s the return of semi-chilly weather earlier in April that has me digging the chance to , well, actually wear shorts now that it’s a bit warmer — regardless, that’s where we’re headed today. Just because you go with a more casual vibe (note the drawstring shorts below) doesn’t mean you have to look sloppy. That’s doubly true even if it rains or it’s breezy — you don’t want just any spring jacket. In the case of the below, we’re talking serious protection from the elements, and some neat heritage style thrown in the mix. Work in some new spring sneakers and an easygoing watch, and you’ll be all set no matter how hard the rain comes down. Sound good? Good. Want to see a different #OOTD? Head to The Style Guide’s Facebook page for a chat!

Casual vibes upgraded thanks to some high-quality brands & subtle style details.

Casual vibes upgraded thanks to some high-quality brands & subtle style details.

The Jacket: Taylor Stitch Beach Jacket in Navy, $128: Another standout from a brand that’s chock full of ’em, this piece is currently pre-funding, but the general idea remains the same — tough outerwear can look great and take you very far. You could also grab a classic JackThreads Mac Jacket and perhaps some light wash denim instead if you wanted something similar now.

The T-Shirt: Bridge and Burn Graphic Tee, $36: The tee keeps this outfit casual (so it’s probably more weekend-minded), but it’s part of some style ugprades we’ve talked about — the graphic is subtle and understated, and the fit is on-point.

The Shorts: JACHS NY Indigo Linen Shorts, $89: Another fantastic style upgrade from standard shorts, they’re easygoing yet not frumpy. If it’s a bit breezy or you want to dress this outfit up, sub in a chambray shirt & dark denim.

The Sneakers: The Hill-Side Standard Low-Tops in Natural Duck Canvas, $175: If you haven’t gotten around to checking out a pair of The Hill-Side sneakers, I’d recommend you do so. Sturdy, well-crafted and stylish!

The Socks: Mack Weldon No-Show Socks, $14.50: The same brand that makes your favorite merino T-shirt also makes some handy socks for that “ankles-out” look so common in the warmer months.

The Trunks: Mack Weldon 18-Hour Jersey Trunks, $22: Just as their socks are worth a look, this brand knows how to craft a great pair of underwear (no, really). Again, an investment that’s also a significant style upgrade from standard boxers.

The Watch: Timex Weekender Fairfield, $75: A downright simple watch for a downright excellent price, ideal for all kinds of casual wear.

The Sunglasses: Spine Optics Aviator Sunglasses, $88.99: As with the above Timex watch, sometimes, simple is better. These sunglasses are durable and remarkably flexible, and won’t upstage the rest of your look.

As with other seasonal spring style suggestions, be it how to dress for Sunday brunch or how to prep for a spring bar crawl, your gear should fit where you’re going. That is, if a T-shirt needs to be subbed out for a slim plaid shirt, that’s the move to make. But alongside that, choosing to upgrade your casual basics — like standard sneakers for a sturdier pair, or old boxers for new trunks — should also be top of mind. Wardrobe reinvention doesn’t have to be done all at once, but small steps can pave the way toward great style. Pick up that Taylor Stitch jacket for me while you’re at it, ehh?

Stay stylish,

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