Wardrobe Basics: Finding Your Style

Q. Hi Jordan,

My question is about style. I have none right now. I used to have a closet full of clothing that I’d mix and match, but I recently went on a closet rampage and gave away some choice pieces because I no longer do a 9-5 – my job now is very casual.

I want to feel feminine, comfortable, and sexy but it seems as though I have NO IDEA what kinds of clothing fit that description. I either end up looking like I am half-dressed for a club or I look sloppy. I like variety, [but] clothing swaps don’t really work for me – tried them, and I run into the same types of issues. Nothing feels like “me” anymore.

I need affordable choices that feel like a reflection of my inside spirit!


– Marissa

A. It can be tough finding your “style footing” after a big transition. I know when I first moved back to NYC from LA it took me awhile to feel like l was both dressing for where I was and dressing like myself. It makes sense that clothing swaps and such aren’t working for you, because the point of those kinds of things are to get pick up fun little extras – a neat jacket, interesting accessories, or a pair of shoes you’d never ordinarily buy – not the kinds of great basics that form the backbone of your wardrobe. What it sounds like you need are a few of those basics, and the approach of fall is always a GREAT time to pull together a classic wardrobe.

It’s hard for me to offer specific outfit ideas for you because I don’t really know what kinds of things you like, but since you’re writing me rather than…you know…someone else, I’m assuming it’s not too far off from my style?

Let’s try this: think about if you were going on a first date. What would you wear, in a perfect world? A pretty sundress? A white tee and jeans? A pencil skirt and a blouse? Whatever the answer is, that’s your “happy place” look, and that’s the silhouette that you should build your wardrobe around.

For me, the answer to the above question is “a loose sweater and low-rise jeans.” But watch: working from that basic silhouette that I know I feel good in, I can style countless different looks.

Right there we’ve got, what, 20 different combos? And I know that I’d feel great in every single one. So while variety in a wardrobe is fun, it doesn’t sound like that’s what you need right now. You need classics in shapes that make you feel great…and then you can add all that fun variety with accessories (that’s what the Forever 21 jewelry rack is for).

Now, let’s talk about those basics.

What I absolutely require in my wardrobe for fall:


– Skinny jeans with a ton of stretch to them (so they’re comfortable – try Vintage Revolution), to wear with flats or boots

– Bellbottom or bootcut jeans (longer hem, to wear with heels)

– Three or four lightweight, loose-ish sweaters with a slouchy, sexy fit (camel, grey and black, ideally)

– A couple of thin, comfortable tanks or tees in neutral colors (I like looser cuts)

– Two boyfriend-style or cropped lightweight cardigans (one patterned, one solid)


– Flat black or navy slip-on shoes

– Flat brown boots

– Chunky heels or wedges (try a lace-up, rugged style this fall)

– Black boots with heels


– Two or three gorgeous patterned scarves

– Brown belt

– Amazing bag (for fall, try teal, red, or a rich brown)

– Jewelry (the cheap stuff is fine, but I like having a lot of options)

– Sunglasses

And…that’s it. Really, if I had just those things, I’d be good 99% of the time. For fun seasonal extras, try a silk bed jacket with a vintage-y feel (H&M has a pretty floral one on sale right now), a pair of red shoes (they’ll go with more than you think they will), a leather cuff, or a summer dress (they’re ALL on sale right now) that you can wear now with flats and a hat, and in a couple of months with boots and a chunky sweater (more on now vs. later dressing here).

I hope that helps!



Product info after the jump…Sweater: Thakoon

Jeans: Seven For All Mankind

Shoes & accessories, clockwise from top left: Linda Farrow sunglasses, Target tortoiseshell earrings, Repetto ballerina flats, Matthew Williamson studded belt, Iosselliani mismatched earrings, Karen Walker tortoiseshell sunglasses, The Alchemist earrings, Dorothy Perkins tasseled scarf, Steve Madden Lakke boots, NARS lip pencil in Baroque, Windsor Store braided belt, Clairashley rose earrings, Sam Edelman leopard boots.

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