What to Wear

Q. I love shoes but since I'm still in school, I have a tight budget. I was ecstatic when I bought these affordable olive wooden wedges from Target! Even though I love them to death, I have no idea what to pair them with. Would they look better with pants or a dress? What about with tights?
- Wear With What?

A. Your new stylish, budget bought wedges will work with skirts, dresses, slim cropped pants and even cuffed shorts. But no tights; these wedges are a warm weather sandal with too many open areas to pull off tights.

Q. I'm a stay-at-home mom of 2 little boys. I recently bought myself a nice pair of brown pinstripe pants on a splurge. They are the only nice pants I own that fit me. The last three "dressy" occasions I attended, my sister-in-law was in the mix of people. Is it terrible if I wear the same pants each time? Should I just tell her the situation? I typically spend my days in jeans. Over the last four years I have fluctuated between maternity clothes, post baby sizes (starting at 10) all the way to my current size 2. We're planning on having another baby soon, so I don't want to invest in too many "nice" clothes that I will rarely get to wear. Any ideas to mix it up?
- Same Pair

A. Don't fret over wearing the same nice pants to several parties; men do it all the time with suits to the office. The best way to mix it up is to always wear a different top when seeing the same guests and choose eye-catching jewelry to additionally distract friends, particularly your sister-in-law. You don't have to worry about size with jewelry so you can be a two or a ten and still wear a cool necklace.

1. Diane von Furstenberg Austral Halter Top, $185 at saks.com
2. TOMMY HILFIGER Paisley Pleated Top, $59.50 at macys.com
3. Beach necklace, $64 at bananarepublic.com
4. Bubble necklace, $150 at jcrew.com
5. Subversive® for Target® Cameo Multi-Row Necklace, $59.99 at target.com

Q. I am so glad to have found your website. It is truly amazing, and you give great advice. I am going to be attending a 4-day conference soon, and towards the end of the conference, there will be a banquet for all of the attendees. The dress code is semi-formal and I have NO idea what to wear. I don't really wear dresses, so any other options would be great.
- Not Knowing

A. You can vamp it up and look stylish without wearing a dress by pairing tuxedo-style pants with a fancy top.

1. Diane von Furstenberg 'Gavin' Tuxedo Pants, $194.90 (sale) at nordstrom.com
2. Lafayette 148 Analisa Silk Blouse, $177.90 at saks.com
3. Robert Rodriguez Ruffle Top, $264 at eluxury.com
4. 3.1 Phillip Lim Leaf-Embroidered Blouse, $345 at eluxury.com
5. 3.1 Phillip Lim Draped-Sleeve Tee, $175 at eluxury.com

Q. I just bought a very cute BCBG dress, but it has fall colors: oranges (light and deep), bone, and dark grey. I am wondering if I could wear such an obviously fall dress in the spring and if so what color shoes and accessories to put with it.
- Wear in Spring

A. While the dress may be darker fall colors, the whether-to-wear-now depends on the fabric. If it is not a heavy wool dress and is made of lighter fabrics then slip it on. The best way to lighten up the look for spring would be to pair it with shoes and accessories that play with the colors of the dress. Opt for light grey patent peep toes or a bright orange strappy sandal. Alternatively, look for a taupe strappy heel that you can wear with many other pieces in your wardrobe. Add bright enamel bracelets to add more color.

Q. I have a short chartreuse colored cocktail dress I am wearing to an event on Friday evening... what color shoes? Black or Gold? The color is a bright lime-y chartreuse 100% Silk.
- Very Sex In The City!

A. Go for gold or neutral strappy heels. Here are some suggestions:

1. Luichiny Primal, $73 at zappos.com
2. Charles David Cascade, $170 (sale) at zappos.com
3. Nine West Dayglow, $83 at zappos.com
4. Nine West Argent, $83 at zappos.com

Q. I have this cute Shoshanna dress that I plan to wear to an outdoor spring wedding. It's an evening ceremony, so I'd like a sweater/jacket that I could throw on top in case it's a bit chilly. Any ideas? Also, I'm wondering what kind of shoes to wear - I have a cute pair of black peep toe heels, but I think I want something a bit more fun. Any suggestions? Thanks! Love reading your advice!
- Cute Seeker

A. Go for a pop of color in your heels and you'll surely strike a pose of stylish sass. Orange or hot pink heels would be ideal to give the dress punch and wear black the next time you pull on the dress and want to keep it simple. As for a jacket or cardigan, choose black or white to keep the look sophisticated. I've chosen several shapes that should work with the dress.

Get the dress: Shoshanna Geometric Print Silk Dress, $350 at nordstrom

1. Theory 'Niba - Deep' Jacket (black or white), $365 at nordstrom
2. Trina Turk 'Minx' Ponte Jacket (black or white), $298 at nordstrom
3. Two Wishes Double Breasted Linen Blend Jacket, $138 at nordstrom
4. Kenneth Cole Reaction Button Front Cardigan (black or white), $79 at nordstrom
5. Lilly Pulitzer® 'Flora' Cardigan, $148 at nordstrom

6. BCBGirls Oriana, $89 at piperlime.com
7. Pura Lopez 'K122' Sandal, $228 at nordstrom
8. Guess Footwear Jelissa, $100 at piperlime.com
9. Stuart Weitzman 'Sharp' Pump, $280 at nordstrom
10. BCBGirls Nice, $90 at piperlime.com

Q. I just got a great new pair of white jeans and now I'm at a loss as to what to wear with them.
- White Uncertain

A. At a loss? How can that be? White jeans are a classic in the Spring and Summer months and the list seems endless of what works with them. Bright polo shirts and striped belts create a preppy look, while striped tops and cropped jackets give an homage to Parisian or nautical flair. Add a button down shirt and a cotton or linen blazer and you're appropriate for casual Friday at the office and shopping chic. For night, pair your white jeans with a flirty v-neck wrap top or a shiny, silky camisole and don't forget the heels. Make sure you have your jeans hemmed as long as you can while wearing semi flats without touching the ground (nobody likes dirty whites) so you can wear low heels to high heeled wedges, strappy sandals or espadrilles.

1. Ralph Lauren Skinny Polo (10 colors), $79.50 at ralphlauren.com
2. Airy ribbon washed favorite tank (6 colors), $29.50 at jcrew.com
3. Solid cross-back tissue tank (8 colors), $48 at jcrew.com
4. Joie Flower Child Bubble Tank (2 colors), $118 at shopbop.com

Q. I love your answers to all the quandaries that people write and do peruse them for helpful hints for me for the future! My dilemma is this: we are going on a Mediterranean cruise in early June. It's a work related cruise my husband has earned. I will know some of the people but need advice/ ideas as to the formal nights. I have plenty of black, but don't really want to be taking black. I love color and wear it well. I am 4 '11 and about 118 lbs and 48. I don't want to look to matronly or too prom-ish! I am having dilemma as I haven't shopped for formalwear in a long time and need to always leave alteration time as well. Any ideas? I am eagerly awaiting your formal flair opinions! Thanks for your help.
- Formal cruise wear challenged

A. Skip the black dresses and embrace color while enjoying the view of intense blue waters. I've found several options both long and short that should make a sophisticated and stylish impression - far from prom styles. You will, however, have to visit your beloved tailor.

1. Phoebe Couture for Kay Unger V-Neck Stretch Satin Dress - Petites', $280 at bloomingdales.com
2. Pencey Sonnies Dress, $417 at shopbop.com
3. Green and Gold Ruched Gowns by BCBG MAXAZRIA, $440 at edressme.com
4. Maggy London Chiffon Gown with Charmeuse Waist, $158 at nordstrom.com

Q. I am a HUGE fan of your website and would love to get your advice. I will be vacationing with my fiancé's family in St. Maarten in mid-June. I have never been outside the states or to such a nice vacation spot. I do not have a clue what to wear that would be comfortable and beach-worthy. I know we will be going around sightseeing, since I am a very adventurous gal. I am in my early-twenties, petite, and looking for some great versatile pieces to wear. Any help would be greatly appreciated! And, could you find some great footwear as well?
-Beach Bummed

A. It's very simple to pack for the Caribbean. By day you'll be wearing a swimsuit, shorts, tanks and short skirts, and by night, sundresses. For shoes you'll need a good pair of flip-flops. I'm a fan of inexpensive Havianas, sandals/flats and one pair of higher heeled sandals or espadrilles. For sandals, consider a metallic pair that will match with all the dresses. And just bring along one small clutch for evening and an oversized bag for shopping and the beach. I shopped for several pieces that should fulfill many items on your packing list and they are all incredibly affordable.

1. Havaianas Flip Flops (7 colors), $16 at saks.com
2. Boutique Nordstrom 'Tabby' Sandal (5 colors), $69.95 at nordstrom.com
3. Xhilaration® Tally Strappy Wedge, $19.99 at target.com
4. Calvin Klein 'Coral' Sandal (2 colors), $89.95 at nordstrom.com
5. Steven by Steve Madden 'Casting' Thong Sandal (4 colors), $78.95 at nordstrom.com

6. Women's Mix-Print Henley Tanks, $14.50 at oldnavy.com
7. Women's Low-Rise Cuffed Twill Shorts (4 colors), $15 (sale) at oldnavy.com
8. Holly Striped Hobo (2 colors), $26.50 at delias.com
9. Women's Embroidered Keyhole Halter Dresses (2 colors), $39.50 at oldnavy.com
10. Lux Lightning Strikes Dress, $68 at urbanoutfitters.com

Q. I just discovered your site today and thought perhaps you could help me. Every time I have to go to a wedding, I end up getting a long, floor length dress because I feel the need to conceal a very noticeable, three-inch-long scar right below my knee. One of my best friends is having her wedding reception outdoors at the botanical gardens in Dallas in June, however, and a dress this long would be inappropriate due to the warm weather. Could you please suggest some calf-length dresses that would be appropriate for an outdoor reception? Also, you should know that I am pear shaped, 5'3'', size 4/6 on top and 8/10 on bottom. Also because of the scar, I only wear slacks to work. Now that summer is coming, I would love a couple of suggestions on skirts and dresses that would be appropriate for work as well. Thank you in advance for all of your help!
- Just So Sick of Slacks

A. I wish I could help you unlock some confidence to bare your scar without feeling self-conscious, but until you're ready, here are a few dress options that are fresh, fun and appropriate for an outdoor garden wedding setting. They should lay fluidly over your bottom half, but you may have to get a little tailoring to have a snugger fit up top. Pair any of these with strappy, high-heeled sandals.

1. Diane von Furstenberg Naro Printed Silk Jersey Wrap Dress, $385 at bloomingdales.com
2. Alice + Olivia Belted One Shoulder Dress, $330 at shopbop.com
3. Lauren Ralph Lauren Petite Linen Sleeveless Wrap Ruffle Dress, $179 at macys.com
4. Diane von Furstenberg Tolara Dress, $365 at shopbop.com
5. Calvin Klein Petite Graphic-Print V-Neck Dress, $148 at macys.com
6. G Wheels Drapeneck Top and Sandy Starkman Printed Skirt, $79 at bloomingdales.com