Personal Shopper: A Winter Wardrobe for Autumn

Autumn writes: Hi Outblush! I need your help with building a brand spanking new winter wardrobe. I've been living overseas in the endless tropical summer of Singapore for 6 years and now I'm moving to blistery Boston in December. I'm excited to move back to the US and to experience the changing seasons again, but I'm also in desperate need of a winter wardrobe. To give you an idea of how bad it is - I don't own a pair of boots, closed toe shoes or even socks (other than gym socks and shoes). The only long sleeve top I have is a cardigan that I wear to the movies. I have a few pairs of light weight work trousers but no jeans. Where do I start?? Please help me build the foundations of a wardrobe so that I can mix and match and add onto it as the months go by. I'm a medium/size 6 in dresses and 8 in shoes, I have about $700 for my shopping spree and my style is relaxed and comfortable yet sophisticated (not sporty or cutesy), I tend to go for solid colors in flattering cuts with interesting details over patterns. Thank you!

Hi Autumn! Trajano here and I am a wizard when it comes to dressing in the cold. I went to the University of Vermont and live in Boston so I knows the snows. When doing big wardrobe overhauls I tend to turn to the Gap family of merchants (Gap, Old Navy, Banana Republic, Piperlime, Athleta). We're not sponsored by them or anything, but they have one shopping cart so you save on shipping and they have almost constant coupons so you can get a big bang for your buck. I concentrated on easy to match separates that'll keep you looking chic and feeling toasty (all the tops and sweaters come in other colors, sometimes like 12). If you're doing any kind of serious commuting wearing a pair of cotton tights or leggings under your pants will make a big difference (the tops of your thighs will freeze and turn purple after about 5 minutes outside in February. The hat, boots, and jacket are a must-have for New England's long, hard cold. The weather may be frightful but Boston is a great town and getting cozy with a hot toddy and some baked mac and cheese is a pretty fine winter-tivity.


1. Gap 1969 Skinny Boot Corduroy pants ($69)
2. Gap 1969 Mid-Weight High-Rise Trouser Jeans ($69)
3. Levi's Bold Curve Skinny Jeans ($84)


1. Old Navy Women's Scoop-Neck Tees ($15)
2. Old Navy Women's Lightweight Boat-Neck Tees ($10)
3. Old Navy Women's Poplin-Stretch Dress Shirts ($27)
4. Boden Hampton's Tee ($38)
5. Boden Wrap Jersey Top ($54)

1. Gap Long Sleeved Scoop-Neck Sweater ($40)
2. Gap Marled Moto Jacket ($65)
3. Hive & Honey Weekend Escape Pullover ($59)
4. Agagra Wrap ($75)

1. Michael by Michael Kors Puffer Coat ($156)
2. North Face Fuzzy Ear Flap Beanie ($35)
3. Calvin Klein Kendall Pump ($)
4. Dr. Marten's Jenny Tall Pull-On Boot ($82)

Frustrated in your search for that perfect leather handbag, red stiletto pump, or whatever makes your heart go thump in the night? Click here to check out our requests for you, the reader, and to contact us, and we might do the shopping work for you in a future Personal Shopper feature!

taylor-bornstein-pic-of-miranda.jpg Trajano here: Conundrums about clothes and accessories are my tasty cup of tea. I am a firm believer in a rich and varied wardrobe so if you want to change, update, or inject some forward fashion into your closet I can hook you up. In my capricious youth I would invest (or squander...don't judge) most of an entire paycheck on a pair of shoes or killer jacket and then live on $27 for two weeks. My dedication to looking lovely runs deep.

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Posted on 10.31.11 at 7:24 AM

The links for the GAP products are wrong.

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