How To Embrace Streetwear (& Not Look Ridiculous)

We may know our way around a slip dress and a tattoo choker these days, but there's still one '90s revival that we'll be fine-tuning for a while: streetwear. A mashup of oversized silhouettes, fancy wild cards (think jewels and faux fur), and the occasional flash of skin, it's a dressing technique that's simultaneously casual and complex. Sure, most of us have some key ingredients — hoodie, crop top, sneakers, bomber jacket. But when it comes to putting them all together in a way that feels more fashion week than running to the bodega, we're looking to the queen of bodysuits and boilersuits alike, Aleali May.

The L.A.-based image consultant, model, and blogger has styled some of the biggest names in music. But if you're like us (a.k.a. far from famous), you can still access a virtual streetwear starter pack with a quick scroll through her Instagram feed. Filled with slouchy cargo pants, body-swallowing outerwear, thigh-grazing band tees, and subtle Swarovski gems, May masters that magic mix — and has 145K followers to prove it. Ahead, she explains her signature '90s-girl-group-inspired style, the sex appeal of baggy pants, and totally owning your look, even when you're wearing sweats. Talk about major street(wear) cred.

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Photographed by Allen Park.
At just 24, you've styled some of the most legendary musicians in the game. Would you say music plays a major role in your style?
"Before I got into fashion, I was obsessed with music — '80s and '90s, mostly. Back then, girls could wear baggy clothes and still look sexy. All the girls in the '90s music scene were so dope. Now it's cool because I actually work directly with musicians and artists. I don’t really care for the word 'stylist' because — just like 'photographer' — anybody can call themselves that. I feel like 'image consultant' better describes the type of styling I do. I’m not just dressing someone — I’m actually providing them with an image and aesthetic."
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Photographed by Allen Park.
Besides nostalgia for the '90s, what else fuels your attraction to streetwear?
"My style is based on comfort. I’m not able to wear heels all day. I run around, and I want to be comfortable but still have swag at the same time. Growing up, you would watch your mom getting dressed every day to go to work. She put on her makeup and had a full routine. Now, we've come into this creative era — and you don’t have to get dressed in this way all the time. Streetwear literally means clothes you wear on the street, and it’s more about comfort and being versatile, so you can work it in many different ways."

Any tips for someone who might be afraid to try out streetwear?
"Confidence is really what makes a look. You can put clothes on a person but, if they're not confident, it’s not going to look as good as it would on someone who just wears it, you know? So that’s honestly the key component. Whether you’re in a formal gown or just a T-shirt and sweats, I think the trick is to just own it."
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Photographed by Allen Park.
Comfy-but-sexy is a look that feels so effortless for you. What's the trick to making baggy clothing look stylish, not sloppy?
"Baggy pants always look great with a fitted top, which adds a sexy vibe. The great thing about many clothing brands today is that they have baggy fits in your actual size. That way, your boyfriend jeans won't be too big."

When you're putting a killer outfit together, what's the first step?
"Definitely my shoes. I can build a whole outfit based on shoes."

Are sneakers usually your go-to choice?
"I wear a lot of sneakers, but with streetwear I like to throw in heels, and that instantly spices it up. You can have the same look but alter it for day or night."
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Photographed by Allen Park.
What's your philosophy on accessorizing?
"I think it's about finding a middle ground. I love jewelry and I feel like it completes any outfit. I like gaudy pieces for certain occasions, but I really prefer simple, detailed, dainty designs. I'm always wearing necklaces and I'm obsessed with bangles — I loved wrapping this Swarovski bangle around my arm for a Cleopatra vibe. I also wear rings sometimes, but I’m just scared to lose them."

What's one weird way you get creative with your outfits?
"I tend to use shoelaces as belts."
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What are the most important pieces for putting together a street-ready winter look?
"The jacket and the boots. If you have those two staple pieces, you can always layer with sweaters and scarves underneath. Invest in a nice, cool jacket that's a different color [from what you normally wear]. I wear a ton of black, so I’ll get a blue jacket to switch it up. Naturally, you’re going to have to get a coat for winter, so go for a [bold] color that will make your outfits pop more."

You're constantly tasked with styling unexpected looks, both for yourself and your clients. How do you recharge and come up with fresh ideas?
"Honestly, it’s a lot of sitting around and looking through magazines. I also do a lot of meditation — it sounds strange, but sometimes I come up with outfits when I’m meditating. Once you find your niche, that's how it is — it just hits you. Or I’ll see a color, fall in love with it, and be like, I need to find a T-shirt in that color."
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Photographed by Allen Park.
What catches your eye when you're shopping for new wardrobe staples?
"I’ve always been drawn to details. So if I'm looking at a jacket, I [might be drawn to] the lining or zippers. I love minimal pieces because they're so intricate."

With the holidays around the corner, do you have any pro tips for shopping for friends and fam?
"I like to shop at a vintage store on Melrose (in L.A.). I usually will get my friends some cool sneakers or a candle."

Do you and your friends have similar tastes?
"Yeah, it's funny because we’ll show up to a place and all have similar combos on. I definitely get a lot of style inspo from my girlfriends — and guys, too. We each have cool, unique swags, and we definitely look like a '90s girl group if you put us all together."

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