Now + Later

So even though Labor Day has (sadly) come and passed… it’s definitely not fall yet. We’re kind of in that in between. Summer clothes seem a little too bright and inappropriate, but fall clothes are uncomfortable since it’s relatively warm out.
This makes planning outfits a little more challenging. The trick is to kind of have one foot in each season. Wear clothes that have a little bit of an autumn-y look, but still casual enough for the summer warmth. It is September after all, and the autumnal equinox isn’t until the 22nd!
I pulled together two looks using one staple piece, the tweed skirt. You can wear them now and later
A tweed skirt seems a bit out of place in the heat of the summer, but it’s definitely doable for this transitional period. Pair it with a casual chambray button down and it works for the next few weeks of September. (Plus, that subtle polka dot is an easy way to incorporate an extra print without going overboard.) A black pair of ballet flats with airy holes has a Summer Meets Fall vibe. 
When things cool off even more, the same skirt can be updated for a great fall look. A grey wool blazer gives the skirt that sharp Ivy look. For super cool days, layer it over a sweater set and add a pair of thick black tights. Flannel loafers (complete with tassels, of course) round out the look.

What is one of your “transitional” pieces? How would you style it for now and later?

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Cardigans! If they're light enough (maybe roll up the sleeves) you can wear them over more summery dresses now and wear them with slacks and flats later.


I love that tweed skirt! I agree that it's the perfect piece to transition between seasons, and it can even be dressed up or worn more casually.

Sarah O'Neil

Capris are definitely my transitional piece. I have demin pairs and dressier mid-calf and ankle length ones that really work for any occasion. However, I'd be lying if I said I wasn't counting down the days until I can break out my sweaters, thick jeans, and boots!