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Q. I am going to a Mets baseball game in April for a first date! I am so excited, but what to wear??? It will probably be chilly and a there’s always a good chance of showers. Do you have ideas for a cute and warm raincoat? I love color, especially jewel tones. We might hang out in NYC after the game, so I’d want to have a cute top and somewhat practical heels that can be worn all day. I want to look cute, but not too dressed up or silly at the game. I’m travelling from Boston for the date so I want to make it count. :) Thank you, stylebakery. Hoping for a Homerun!

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A. A Red Sox fan at a Mets game for a first date, he must be a special guy! This is definitely a tricky outfit to pull together: sporty and comfortable, yet appropriate for a first date and an evening in NYC. When it comes to date dressing, I think it’s always best to lean a little bit towards classics, rather than trendy items. Guys don’t always “get” trendy. Even when choosing classic pieces, you can still have a little fun with your look and mix in some chic accessories.

The look below is a chic, classic, comfortable early spring look. Start with a pretty top and slim ankle cut jeans, then add a comfortable flat in a pop of color and a bold necklace. Finish the look with a classic trench and a cross body bag - you’ll look pulled-together without looking like you’re trying too hard at a baseball game. If the weather is very chilly, you can always add a scarf, or even a sweater if necessary. If it’s too cold for bare ankles, add a pair of flat boots instead. Have fun!

Q. I’m going to a wedding in LA next month and absolutely stumped at what to wear. It’s going to be at a country club in the mid-afternoon. I was told suits for the guys, but wasn’t given any indication on what to wear as a girl. I’m 5’8, size 12-14, with a smaller waist and more junk in my trunk, and I want to also look as slim as possible! What do I wear??

A. Afternoon weddings are my favorite! They are a great excuse to get dressed up and wear a pretty dress, without having to invest in something black tie. In other words, you’ll get a lot more use out of the dress you choose! Play up your assets with a fitted top that shows off your waist and shoulders and look for a skirted bottom that flares out to conceal your “junk”.

For a spring afternoon wedding, I love a pretty printed dress, so here are a few options to choose from. Add a pair of heels, some fun jewelry and a pretty clutch and you’re all set!

Q. I am looking for a pair of really comfortable pants that don’t look like run-of-the-mill sweats but that I can wear and feel as though I’m wearing run-of-the-mill sweats. I’m afraid of yoga pants because they accentuate every flaw and I have to stand by my belief that leggings should not be worn as pants (and yoga pants are, essentially, leggings with flared bottoms). Can you help me find something comfy that I could actually wear in an airport without feeling like a slob and that I don’t need to wear special underwear with?

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A. If you’re really looking for an upgrade to run-of-the-mill sweatpants, you’ll be thrilled about spring’s new dressed up sweatpant trend. Though I’m not sure I would spend $175 on a pair of Alexander Wang sweats, there are more affordable options available from a variety of designers. Here’s a selection of super cozy sweats to wear on the street, not at the gym:

Q. I recently bought a long navy skirt from Anthropologie that I plan to pair with a tank and flower belt in the summer. I was surprised that at 5’2” I could pull this look off but the darting and flowiness of the skirt work on me. Plus, I plan to wear the belt at my natural waist to make my legs seem even longer. However, I am confused about what shoes to wear. I don’t want to pair it with flats because I am afraid that it would look dowdy. I am not sure that I should introduce gold or silver gladiators to the look either. Do you have any suggestions? Please note that I am a mom chasing around my 9-month-year old so I can’t really rock stilettos but I am open to a comfortable wedge or short heel.

A. One of this season’s top trends, the maxi skirt, looks great worn with platform sandals in the spring and summer. Whether you prefer a high wedge or one of the new “flatform” low wedge styles, here are some options to pair with your new skirt:

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Q. I’m attending my first-ever writers conference at the end of January, and am feeling a little lost about what to wear. From what I’ve heard, most of the people do business casual or dressier casual attire, and a suit would be a definite no-no. I usually feel more comfortable in a dress, but since the conference happens to be during winter in NYC, that might not be the best of ideas. There will be a lot of standing/walking around, so heels won’t really be practical either. I’ll be pitching my new book idea to some literary agents and I want to look professional, yet creative. There will be a lot of potential authors there, so I’d like to stand out (in a good way). I’m also very petite so I don’t want to look like I’m playing dress up in my Mom’s business clothes!

A. I love when you can infuse a bit of creativity into a work look. Since you feel most comfortable in a dress, wear one! We New Yorkers wear them all winter long - just add some opaque tights and a pair of boots and you’ll be fine. To add a creative touch to your dress, try pairing it with a sleek leather jacket. Another option is to pair skinny black pants with a belted jacket and booties. Add a stylish accessory like some great jewelry or an animal print belt or scarf, and a chic tote.

Though I understand the need to wear comfortable (and perhaps flat) shoes if you’ll be on your feet for hours, your best bet is to look for a stylish pump or shoe with a mid-size heel - this will help you to stand out a bit more since you’re so petite (sometimes we have to suffer a bit for fashion!) Find a shoe that you’ll be comfortable enough in that still offers a little bit of height and will add style to your look.

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Below are some looks for inspiration:

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