Every October, I start the slow but steady summer-to-fall wardrobe swap. Bringing back boots and storing sandals. Shorts for slacks, tanks for blouses, etc. This is also a great exercise to rediscover some of your chilly-weather favorites and think about new outfit combinations. Having a handful of outfit formulas to rotate for the season makes getting dressed less hectic, but still stylish. Here is a rundown of some outfitting combos to consider as you shop your closet or look to fill in gaps.
First up, a short trench + straight-leg jeans + loafers. This combo can be worn on repeat once temperatures start to dip below 60 degrees. It’s the kind of outfit that looks put-together in under five minutes. You can wear it with a T-shirt, sweater, or button-down. Now, I know you’re thinking, why a short trench? Well, I’ve found that full-length trenches can get bulky, while a more cropped version like Gap Factory’s Relaxed Cropped Trench is just as chic but has more ease of movement. You can easily swap in a barn jacket for a trench style with this combo for a more rustic look. Or, if you’re looking for an alternative to a traditional trench, there’s Athleta’s Daymaker Jacket; similar to a trench but more functional with its water-resistant material and hood for those fall sprinkles. And yes, I have highlighted this Daymaker jacket in a previous piece, and no, I’m not getting any sort of endorsement from the Gap family of brands.
Next up, one of my new favorite combos: Cardigan + oversized sunglasses + leather bag. Why I like this so much is because with the accessories and cardigan, it can elevate the look underneath. You can go with a lightweight cardigan like Lands End’s Fine Gauge Cotton Crew Cardigan as the season unfolds. As we head toward late fall, swap out for a grandpa-style chunky cardigan. I try to source big, oversized cardigans from second-hand and thrift stores. Why not get the grandpa look from the wardrobe of actual grandpas, right? Contrast the coziness of a cardigan with sophisticated round sunnies like Ray-Ban Women’s Sunglasses available at Macy’s and currently on clearance. A great pair of sunglasses will also add polish to any look. As for a leather bag, if you don’t already have one, look to thrift stores or secondhand resellers for mid-level designer bags at a bargain.
From bags to stripes. Striped tees and shirts can be quite the workhorse in outfit formulas if you remember to wear them. Stripe shirt + black pants + black blazer. A black blazer and a striped tee might be the most reliable outfit formula out there. Swapping jeans for black wide-leg trousers makes it a touch more polished for an office setting without losing any of the ease. To get a bit more use out of some summer pieces, go for a striped shirt + linen pull-on pant + ballet flat. Or, if you’ve put away your linen for the season, swap in a jogger instead. I love the combination of a classic black-and-white striped shirt with an easy, solid-colored, preferably black, but a contrasting shade like red or sky-blue works, pant. And then either a pop-of-color flat or a patterned flat, like an animal print. Old Navy’s Soft-Knit Pointed-Toe Ballet Flat in leopard will contrast nicely with a graphic striped tee, with the solid bottom giving space so as not to clash. Remember, contrast creates interest, while clashing causes disruption.
If you’re feeling like disrupting a bit here in your look, go for it with dress + pants + vest. I do not recommend this formula for outfitting novices. This is for the tried-and-true outfitter because to disrupt in a stylish and not foolish way takes the right combo of pieces, fit, silhouette, and fabric. So, approach with caution with a shirtdress (which acts like a button-up), trousers, and a suit or sweater vest. A dress like J.Jill’s A-Line Shirtdress in black and white stripes provides some length and drama when paired with a baggy-ish full-leg pant like Halara’s High Waisted Zipper Pocket Wide Leg Work Pants in a mirrored black and white stripe. Create some shape and balance the proportions with a tailored vest. A shorter version like Madewell’s Tucked Mini Shirtdress can work with a more cropped fitted trouser and a more casual knit vest. Again, this formula is not for the faint of heart; outfit with care.
There are a few more formulas to share in part 2, but for the time being, think about these looks as being less about specific pieces and more about combinations. This styling approach works best with what’s already hanging in your closet.
