MY FALL FASHION SHOPPING STRATEGY

A couple of weeks ago I published my first post about the topic of money (one I’m excited to talk more about!) – and it was all about how I set myself up for financial health and changed my money mindset. Well, if there was ever a time to test my own willpower – it’s the fall fashion season. I blame it on the fact that as a kid the only real “shopping spree” I ever got to go on was for back to school, when my Mom would take my sister and I to pick out a new pair of jeans, new shoes and a few other new novelty items before the school year started – and it felt like SUCH a treat. Flash forward to being an adult, the onslaught of new arrivals, magazine’s September issues and the fact that I just truly love fall clothes.. and it can be really hard to stay on track. This year, I was determined to do things differently though. And so I came up with a strategy.

Rule One: Don’t buy anything in July. Or August for that matter. If you haven’t unpacked your sweaters from storage, it can be really easy to forget that you do in fact already own an oversized cream cardigan and before you know it, you’ve bought a second one. Last week, I dutifully flipped my closet and found myself excited about all of my favorites that I already own and get to wear again this season. While you’re doing this, think about which pieces you wore most last year. If it was crewneck sweaters, maybe you could use a new one to add to the rotation. If you remember feeling like you never had any cute blouses to wear to work, keep that in mind as you shop.

Rule Two: Make a good old fashioned moodboard. Or a Pinterest board. Or hit save on Instagram. Back in high school, I used to pour over magazines and whittle down the one or two key pieces that I could buy into (on a budget) – maybe it was one cool pair of boots or a particular handbag silhouette – and the rest I would try to find in my own closet. I started doing this again and SO many of the looks I was seeing in my inbox or on Instagram, I could nearly recreate with pieces I already owned. I just had to ignore the shiny new version. Below are looks from Veronica Beard, Sezane and Reiss that I loved.

Rule Three: Make a list. Write out the things you still really have your heart set on, and be specific. You’ll be able to see that three pairs of ankle boots are on the list.. and can clearly cut back. Or the fact that three fancy dresses are on there, but you end up in jeans and a t-shirt everyday and you work from home.. so maybe re-think that. Note the prices and estimate a rough cost per wear (a $40 trendy sweater you’ll wear 2 times has a $20cpw while a $140 camel cashmere sweater you’ll wear 40 times this fall has a $3.50cpw). While it’s nice to add a couple of fun things into the mix to refresh your existing wardrobe, be realistic about what you feel comfortable in and where you want to put your money.

Now the fun part – shop for the things left on your list. I mean, wait for sales.. but then, you know, go for it. Below – the things I’m spending on this season and why:

  1. Plaid Miniskirt – In the past ten years I’d say consistently the item I wear most in fall is a plaid miniskirt. To work with tights and a button down shirt, for a date night with over the knee boots or casually with sneakers and a crewneck sweater. It’s my signature style. I love this one with the hits of green and know I’ll get tons of wear out of it.
  2. Patent Leather Loafers – I had a pair of black patent ankle boots and black patent leather flats that I literally wore to shreds over the past three years and finally had to toss them both. This feels like a hybrid. I tried on in store to be sure they passed the ‘walk to work’ test too.
  3. Simple Cardigan – I eyed this fluffy cardigan ALL of last fall and winter and didn’t pull the trigger but this year I’m doing it. I love that you can wear it with the buttons in front or back, all buttoned up or off the shoulder for a cool, undone look. So simple, so chic.

ON CAREER: WHAT KEEPS YOU UP AT NIGHT

I think its safe to say that work keeps a lot of us up at night. Stress over your next career move, worry about a big project deadline.. as an adult these are the things that go bump in the night.

I’m a notoriously good sleeper. I’m asleep before Adam’s head has hit the pillow after kissing me goodnight. Give me an 8 hour flight and I’ll be asleep before we’re off the tarmac.. the stewardess gently nudging me at landing. But lately, I’ve been waking up in the middle of the night consumed with thoughts of work.

I moved into a new role at the beginning of the summer and its been stressful as I transitioned into a more managerial position. Each week, without fail, come Wednesday or so and I’d start to get restless in the night. The sounds of sirens out my window not enough to drown out the noise inside my own head. Little things that I needed to add to my to-do list or bigger picture things like budget planning for 2020. And what’s worse is that first my brain would think of work and then it would veer into new (old) territory – that time I said the wrong thing to that person 7 years ago. The perfect comeback line I should have used on that ex-boyfriend. How it would have been best to stop at three tequila shots that time at that bar. You get the idea. It seems my transition at work was strangely digging up my entire past.

Joan Didion once said “I think we are well advised to keep on nodding terms with the people we used to be, whether we find them attractive company or not. Otherwise they turn up unannounced and surprise us, come hammering on the mind’s door at 4AM of a bad night and demand to know who deserted them, who betrayed them, who is going to make amends.” This summer has been the first time I truly understood her.

But then last week – something changed. I launched a project at work and was really happy with the results, then came home and had spent the evening feeling very excited about a side project I’ve been working on, thinking about how it perfectly combines some of my passions and will be a great creative outlet besides my full time career. That night I predictably woke in the dark, but this time – my mind was bright with ideas. I was back asleep before I knew it. I’ve been sleeping soundly ever since.

It turns out – you may need to shake your mind awake so that you can sleep. There’s always going to be things to be stressed about (career-wise or life-wise), but for me at least – once I managed to flip the script and think of all the possibilities of the future, the missteps of the past started to quiet down in my head. Here’s to a solid eight hours.

SHOP THE STORY:

THE BEST FALL SHOES TO SHOP NOW

There are few things that soften the blow of summer’s impending end to me.. but fall footwear is one of them. This past weekend I felt the first of fall’s cool air creep in and promptly did what any rational New York woman would do.. I went shoe shopping. The picture above shows the two perfect pairs I snagged and the rest I’ll just be dreaming about from now until when fall truly shows up. I’m not rushing it though.

SHOP THE POST:

LINEN BLAZER + CUT-OFF DENIM SHORTS

In general, I’m not a very casual dresser. I don’t wear leggings out of the house unless I’m going to the gym and I never got on board with the whole athleisure trend. It’s not to say I don’t think it looks good on other people, it’s just not me. That being said – one casual piece mixed into with other more classic pieces feels right for a hot summer day. Case in point: these jeans shorts paired with a linen blazer, statement earrings and neutral block heels.

SHOP THE POST:

I’ve always just felt that life (and especially New York) is worth dressing up for. What if you run into an ex? Or a potential boss? Or a reallyyyy pretty West Village street. Dress for the neighborhood you want to live in, right?

In full disclosure, these jeans were Adam’s and were only slightly too small for him so he gave them to me to cut-off (I won’t dwell on the fact that we have nearly the same sized waist…), but pretty much every thrift store in America has a good pair of vintage Levi’s that you could do the same with. I say that because there are an somewhat alarming number of girls on Instagram wearing $150 cut-off jean shorts and raving about how amazing they are. Here’s an alternative.

And while I’m giving out advice – this bag has been one of my favorites since spring and is now on sale. It will be a wardrobe hero straight through fall. I tied on this vintage Liberty London silk scarf that I bought in a nearby vintage shop about 10 minutes before we snapped these photos. Even my bag’s like to dress up apparently.

CHIC SUMMER STYLE ON THE UPPER EAST SIDE

I’ve been thinking a lot about identity lately. How we define ourselves and how important or unimportant that really is. On a podcast I listen to (Happier with Gretchen Rubin) they recently mentioned how often we “identify” as something but actually aren’t putting in any real work there. For instance, if you call yourself an artist but haven’t actually set aside time to pick up a brush in years. You’ve got to check in every so often and make sure you’re prioritizing the identities that are most important to you.

I identify as a vintage lover, a classic style-type and a sentimentalist – it’s what makes me love holding on to clothes for years. It’s why I don’t find the idea of Rent the Runway’s unlimited program (where you basically borrow clothes to wear and return for a flat monthly fee) very enticing. There’s just no story there. You wear it once and it’s over. And for awhile I felt a bit of pressure that I needed to be wearing/sharing something on the blog that was always buyable. Something new and noteworthy. But nothing in these photos is still available to shop, and I love each of the items anyway. And I want to share them anyway. That’s what feels true to my identity.

To note, if ‘trendsetter’ is an important part of your identity then maybe you’d feel the opposite when it comes to a shopping strategy. And that’s cool too. Just recognize what feels true to you and follow that lead.

It’s why I also re-prioritized reading in my life, travel over more clothes purchases and spending time with Adam, friends and family whenever possible over quite so much work. At the end of the day, I want to be an avid reader, world-traveler, good partner, friend, sister, daughter and Aunt more than a success at Instagram. And it feels nice to remind myself of that from time to time.

Get a similar look: