Do you feel like you forgot how to get dressed? If you do, you’re not alone. Between working from home (in sweats) and coming off an active summer (in tank tops and shorts), you may have forgotten how to pull yourself together. And create complete outfits that make you feel good. And look stylish and cool at the same time. And now that fall weather is on the horizon, you’re not feeling ready at all.
Don’t worry, I have a solution. Here are a few outfits that work for most every body type and function for different occasions. And they just make you feel like a ‘cool girl’ – you know what I mean, right? Those women on Instagram that always seem to have it pulled together – and make it look so effortless. The good news is that it can be just as effortless for you with a few versatile outfit ideas. And the best part is that you can wear a version of these outfits right now. And easily adapt the same outfit ideas to cooler fall weather.
Take a look at 3 never-fail cool girl outfits, with tips on wearing them from late summer September right through late fall December.
BLAZER, GRAPHIC T & JEANS
This is seriously a never-fail cool combo – and you can adjust the items to work for your individual style and wardrobe. Don’t have a print blazer? Go for a solid one. Prefer a striped t to a graphic t? Switch it out. And play with whichever denim fit and wash and color you like. It’s the epitome of laid back (but still put together) cool.
Above is a perfect example of how to wear this look right now – pair a light or midweight blazer with a fun graphic t, pale blue jeans and slides. Push up your sleeves, pop your collar and you’re ready for a casual lunch or movie date. (And then read this for 3 fall looks I created with one plaid blazer.)
Shift this look right into cold weather with a few simple swaps. Trade your lightweight blazer for a wool one. Since graphic t’s are easier to find than graphic sweaters, a striped sweater works just fine. And grab a comfortable boot – yes, it’s that easy.
STYLE TIP: Switching seasons is less about individual items and more about fabrics. If you love a crewneck t-shirt, heavier knits and thin crewneck sweaters can act like your t-shirt layer as you head into fall/winter.
Top outfit: Rails blazer. Anine Bing t-shirt. Veronica Beard jeans. Steve Madden mules. Warby Parker glasses. Capucine de Wulf bracelet.
Bottom outfit: Anine Bing blazer. Nordstrom Signature sweater. Re/Done jeans. 3.1 Phillip Lim boots. Warby Parker glasses. Uno de 50 bracelet.
DENIM JACKET & PRINT SKIRT
You may have already worn this outfit – but it’s still a great ‘I want to look pulled together while I’m running around’ look. It’s a straightforward combination of wardrobe staples (denim jacket, solid t-shirt, white sneakers) plus one interesting piece (print skirt) that’s much more than the sum of its parts. And it can take you everywhere from weekend errands to meeting friends for coffee to the first parent meetings of the new school year.
Turn up the style volume with the same basic pieces translated into fall. A roomier denim jacket (that works with a sweater underneath) and boots are all you really need (tights optional). And if you’re tired of your denim jacket, here are 3 options that work just as well.
STYLE TIP: The same print skirt that you wear in summer can work right into fall in transitional fabrics – but be aware of the print you pick. Prints with a light background tend to feel more warm weather, while dark based prints feel right any time of year.
Top outfit: Veronica Beard jacket. Agolde t-shirt. Vero Moda skirt. Vince sneakers. All Saints earrings.
Bottom outfit: Anine Bing denim jacket. Simon Miller sweater. Veronica Beard Skirt. Vince Camuto boots. Lauren Ralph Lauren earrings.
FEMININE DRESS & MOTO JACKET
This look is all about juxtaposition – a feminine dress in a floaty fabric balances a masculine shaped moto jacket. It’s always an interesting combo, and a good reminder that you don’t necessarily need a dressy jacket to wear over your nice dresses.
The late summer/early fall version of this outfit is all about ease – an on-trend slip dress, light suede jacket and sandals work for any occasion from a cocktail party to dressy date night. (Even with a full social calendar, you don’t need a big dressy wardrobe – click to see the 5 dressy pieces you need.)
Shift into chillier temperatures with heavier fabrics and a little more coverage. A long sleeve dress, leather jacket and suede boots maintain the cool girl vibe.
STYLE TIP: A change of accessories also transitions outfits from summer to fall. Straw bags feel specifically summer, so store them once the weather changes. And there’s no need to freeze your toes off in sandals when sleek boots look just as good.
Top outfit: Blank NYC jacket. Anine Bing dress & sandals. Baublebar necklace. Loeffler Randall bag.
Bottom outfit: Anine Bing jacket. Intermix dress. Schutz boots. F+H Studios necklace. Cult Gaia bag.
Are these outfits new to you? Or have you tried them before? Comment to let me know.
If you’re looking to add a little ‘cool girl’ into your style, click here to schedule a free Zoom consultation. We’ll chat about your needs, I’ll let you know the process I’ve used with hundreds of clients and you can ask any questions about what it’s like to work with a stylist.
And if you want some more information, click here to read about my Re-Style Framework. And click here to read what a bunch of my clients have to say about the process of evolving their style.