Making the Switch: Dressing for the Transitional Season

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The change in seasons is one of the things that makes dressing well fun. There is always something to look forward to, be it wild madras in summer or luxurious tweeds in winter, and the simple act of swapping your wardrobe, or “shopping in your closet,” can be as fun and refreshing as buying new clothes. But what do we do in those transitional times when it’s too hot for one set of clothes, but too late for another? You don’t have to be the guy in a parka and flip flops (athletes from the Cayman Islands at the Sochi Olympics get a pass).

Labor Day has just passed, and that means it’s time to stash the wild madras, seersucker, and faded pastels of summer. And yet, as I write this, the temperature is approaching ninety degrees. Obviously, it’s too soon to wear tweed and corduroy, but full blast summer clothes just don’t seem right either. Creating outfits that are appropriate for the weather and time of year can be tough, but certainly not impossible. Here are some tips to help you get through the “shoulder season” in style.

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Keep It Simple

The most important thing to remember is to dress for the weather in a way that is comfortable. You may be dying to wear that new sweater or those great flannel pants you picked up a while ago, but if it’s too hot and you’re sweating in them, you won’t look good. At the beginning of fall, when temps can still rise, stick with a classic selection of simple items. Crisp khakis and a blue shirt are appropriate year round and, being cotton, they are comfortable in the heat. Dress it up with a navy blazer in a year-round weight and a tie, or just wear the combo as is. If it’s still hot enough, feel free to continue to skip the socks.

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Wear Long Sleeves

It may still be hot enough at the start of the season to wear shorts, and that’s fine. Try wearing shorts with a long sleeved shirt instead. With the sleeves rolled up, you’ll stay cool but not look like you’re hanging on to summer too much.

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Introduce Darker Colors

Start phasing in the darker colors and richer textures of fall slowly. You can keep wearing that lightweight tan jacket, but try pairing it with darker trousers and a knit black tie for a look that keeps you cool but still nods to the time of year. With a look like this, putting socks back in rotation is a must.

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Opt For Mid-Weight Items

As the weeks wear on and temperatures cool, those heavier fall clothes will come into their own. But, it likely won’t get really cold in a day. Put a tweed or two in a lighter weight in the closet, but save the burly stuff for really cold days. On a cool (not cold) day, a lightweight tweed has the advantage of working equally well with cotton chinos as it does with heavier wool slacks, giving you a degree of versatility that a heavier coat lacks.

Dressing for the heat of summer or the cold of winter is relatively easy, but with just a little thought and attention to the weather on a day-by-day basis, transitional dressing can have a style all its own. Use these tips in reverse order when the spring rolls around, and you’re set.

Photo credits: An Affordable Wardrobe

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