Michelle Dalessandro: "I don't have a chest, so baby doll tops work great for me."
  • Michelle Dalessandro: "I don't have a chest, so baby doll tops work great for me."
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I stopped folks from Chula Vista to Del Mar, at the malls and on the street, to ask them about their clothes. Questions ranged from sartorial specifics ("Why this outfit?") to cautionary tales ("Your biggest fashion mistake?"). And I asked what they hated to see on other San Diegans. It's just as you suspected: everyone is watching you...


Michelle Dalessandro, 25, Fashion Student, Golden Hill

This outfit was about $250 to $300. Leggings from American Apparel. Baby doll shirt with capped sleeves and string of gold pearls and plastic gold bangles from Studio 1220. The boots from Anthropologie are somewhere between 16th-century Elizabethan and Louis XIV. I always spend my money on accessories. I look for unusual fabrics -- those that cost less but look like they cost more. I pay attention to the way clothes are designed, the way they fit. If it doesn't fit well, I won't get it. Leggings are a staple for me; they're comfortable and I always wear them. I don't have a chest, so baby doll tops work great for me. The shoes are very me -- the girl in me: very feminine, lots of detail, and a little fur.

I wish I didn't have to hem my pants. I wish I could wear long, long pants and long dresses. If money were no object, I would buy Louis Vuitton, Max Mara, Betsey Johnson. I usually don't regret anything I've worn because everything is intentional when I get dressed. That said, I once wore sandals to a Scarlet Symphony concert and started a dancing pit -- a case of choosing the wrong outfit for the wrong occasion. I wish people would buy the right size, what looks good on them, not just what's in style.

As far as what women in San Diego wear, there's definitely a retro vibe in San Diego, and the women that do it, do it well. Otherwise, women seem to have a lack of imagination and confidence. And they need more color! More color, more confidence.

Barbara Dooley

Barbara Dooley, 27, Personal Banker, Pacific Beach

I'm wearing one of my favorite dresses that is super cute and super comfy. I bought it at H&M for $35. I decided to pair it with some boots -- BCBG, $100. My sunglasses are Marc Jacobs, and the purse is Helen West. Both were about $100, so this outfit costs about $335. I like to add odd, unexpected colors with what I'm wearing, so that's where the necklace and tank top come in. I don't go by brand at all...just cuteness and style!

I chose this dress because I bought it at a store that we don't have in San Diego. That way I won't see myself walking down the street! I think this style dress is very flattering on all different body types. I like the wrap part because it accentuates the waist.

I'm very fortunate because I don't feel limited in what I can or can't wear. Some pant styles are really cute, but they aren't long enough for me. If I could afford whatever I wanted, I'd probably buy big-name designers.

I could always use a second opinion — or a third — before I leave the house, but I try not to make many mistakes or go to extremes with what I'm wearing. Sometimes it's hard to keep up with changing fashion seasons — new styles can get expensive. We've all had our own personal episodes of What Not to Wear! I don't think women should lie to themselves about what looks good on them. Just because it's in style doesn't mean it's right for them. On the other hand, I think that the way a woman dresses says a lot about her personality and how she views herself. -

Linda Cobo, Downtown

Linda Cobo, 18, Student, Sales, Downtown

I'm wearing a yellow, gray, and black printed dress and a black knitted shrug. My mom made the whole outfit for me. She's been making dresses since she was 15; she learned it from her mom, who was also a dressmaker, my grandma. In Mexico, my mother made everything -- wedding dresses, you name it. I just give her a copy of the dress and she'll make it even better...she's very creative. I'm also wearing patent leather flats from Saks Off Fifth. The whole outfit probably cost me $70 -- $20 for two yards of material, $30 for the shrug's yarn, and $20 for the shoes.

I like wearing dresses; I'm a girlie girl and have been since I was five years old. But I'm too short to wear long dresses or long skirts. I wish I could afford BCBG and Marc Jacobs.

Before I choose an outfit, I run it past my mom. She always knows what's right because she makes clothes, and it helps me avoid fashion mistakes. Certain members of my family aren't as lucky: one of my cousins still wears short tops -- you know, styles that are over with already...something that was in a year or two ago, and she's still wearing it. I don't like baggy jeans on anyone.

Christine McLaughlin, University Heights

Christine McLaughlin, 35, Retail Management, University Heights

This is a wool-blend suspender skirt from Cassette that I bought at Neighborhood Boutique. I got the yellow tie-dyed T-shirt there too. Everything except the vintage combat boots, which I bought at a thrift store in Chula Vista. The whole outfit was probably under $200. I chose this skirt because it's edgy and fashion forward, and suspenders are big again. I like to mix different eras -- the new skirt, the combat boots from the early '90s. I love Prada, Anna Sui, Moschino, Comme des Garçons -- the modern design element, it's genius -- but I can't afford it.

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